Fragrance Compounds

Abstract

Compounds according to formula (I) Ketone or aldehyde represented by formula (II) of JPEG2024523397000014.jpg3974 Its use as a precursor in perfume production to produce JPEG2024523397000015.jpg3067 is described.

Description

[Technical field]

[0001] Technical Field The present invention generally relates to fragrance precursors capable of releasing fragrant carbonyl compounds such as aldehydes or ketones.The present invention also relates to perfume formulations and consumer products containing said precursors.The present invention further relates to the methods of making said perfume precursors, perfume formulations and consumer products, and the use of said perfume precursors and perfume formulations in consumer products such as personal care and household care products. [Background technology]

[0002] background Fragranced consumer products, such as cleaning or laundry products, containing fragrances are well known in the art.However, it is known that fragrances can change when incorporated into certain consumer product bases, such as through decomposition caused by interaction with air, or due to the presence of oxidizing agents such as alkali, acid, hypochlorite, or other base ingredients, which can lead to chemical decomposition of fragrances.In addition, volatile fragrances tend to dissipate over time.Furthermore, when used in cleaning or laundry products, the attachment of fragrances on treated substrates is weakened by washing and / or rinsing procedures.

[0003] Nevertheless, consumers would like to have products that can be stored over time and still give a consistent scent impression. In particular, the impact of volatile components should be preserved. Furthermore, it is desired that such products produce a long-lasting, pleasant scent that slowly emanates over time from the treated substrate.

[0004] To address these needs, fragrance precursors, substances that are essentially odorless by themselves but that decompose under certain circumstances to release fragrance molecules, can be used.

[0005] There are several classes of known precursors that release fragrance molecules upon activation, such as hydrolysis, temperature change, oxygen, light and enzyme action. For example, WO2012085287 reports a group of precursors that can release fragrances by spontaneous air oxidation. WO2007143873 describes another group of precursors that can be cleaved by hydrolysis.

[0006] All precursors show different stability and release fragrance molecules under different conditions.There is still a need to provide additional precursor systems, for example to improve the fragrance effect after several days on dry fabric.Therefore, it is desirable to provide new or improved systems that can release fragrance over a long period of time and provide long-lasting release of said fragrance. Summary of the Invention

[0007] According to a first aspect of the invention there is provided the use of a compound as a fragrance precursor capable of releasing a fragrance over an extended period of time and providing a long lasting release of said fragrance.

[0008] According to a second aspect of the present invention, there is provided a precursor compound.

[0009] According to a third aspect of the present invention, there is provided a method for releasing a fragrant ketone or aldehyde.

[0010] According to a fourth aspect of the invention, there are provided methods of making the perfume precursors, perfume formulations and consumer products.

[0011] According to a fifth aspect of the invention there is provided fragrance formulations and consumer products comprising said compounds.

[0012] According to a sixth aspect of the invention there is provided the use of the perfume precursors and perfume formulations in consumer products such as fabric care, personal care and household care products.

[0013] Details, examples and preferences relating to any particular one or more of the described aspects of the invention are described further herein and apply equally to all aspects of the invention. Every combination of the embodiments, examples and preferences described herein, in all possible variations, is covered by the present invention unless otherwise indicated herein or clearly contradicted by context. Description of the drawings [Brief description of the drawings]

[0014] [Figure 1] FIG. 1 shows a comparison of precursors and free aldehydes used in liquid detergents. [Diagram 2] FIG. 2 shows the stability of the precursor in liquid detergent. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] Detailed Description The present invention is based on the surprising discovery that nitrones can serve as fragrance precursors capable of releasing fragrance compounds bearing a carbonyl group. These fragrance precursors provide a delayed release of the carbonyl compounds over a longer period of time than is possible by use of the fragrance itself.

[0016] Thus, the present specification provides a compound of formula (I): [ka] A ketone or aldehyde represented by formula (II) [ka] and use of the compound as a precursor for producing During the ceremony R1 is, Straight or branched C1-C 15 Alkyl, e.g., C6, C7, C8, C9, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Alkyl; Straight or branched C1-C 15 Hydroxyalkyl, alkoxyalkyl and alkylthioalkyl, for example, C6, C7, C8, C9, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Hydroxyalkyl, 4-(hexyloxy)butyl, 3-(methylthio)propyl; Straight or branched C2-C 15 Alkenyl, e.g., C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C210, C22, C30, C41, C51, C61, C72, C81, C92, C19, C23, C34, C45, C46, ​​C47, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Alkenyl; Straight or branched C2-C 15 Hydroxyalkenyl, e.g., C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C210, C220, C23, C24, C25, C36, C37, C38, C39, C40, C41, C42, C43, C44, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Hydroxyalkenyl; C3-C8 cycloalkyl, such as cyclopentyl or cyclohexyl; C3-C8 cycloalkyl (e.g., cyclopentyl or cyclohexyl) substituted with one, two, or three groups selected from C1-C7 alkyl (e.g., ethyl, isopropyl, tert-pentyl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; C5-C8 cycloalkenyl (e.g. cyclopent-3-enyl, cyclohex-1-enyl, cyclohexa-2,4-dienyl, cyclooct-3-enyl); C5-C8 cycloalkenyl (e.g. cyclohex-1-enyl, cyclohex-2,4-dienyl, cyclooct-3-enyl) substituted with one, two or three groups selected from C1-C7 alkyl (e.g. ethyl, isopropyl, tert-pentyl), C2-C7 alkenyl (e.g. isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl and C3-C5 cycloalkyl (e.g. R1 is 7-methyl-spiro[4.5]dec-8-en-6-yl, spiro[4.5]dec-7-en-7-yl, 5,5-dimethylcyclohex-1-enyl, 2,6,6-trimethylcyclohex-1,3-dienyl, 2,4-dimethylcyclohex-3-enyl, or 4-isopropenyl (cyclohex-1-en-1-yl)); (C1-C3)alkyl(C5-C6)cycloalkyl, where the cycloalkyl ring is optionally substituted with one group selected from -OH and =O groups, and / or one or two ether group(s), and / or up to four C1-C7 alkyl groups (e.g., R1 is (3-tertbutylcyclohexyl)ethyl, or (4-(1,1-dimethylpropyl)cyclohexyl)methyl, (3-oxo-2-pentylcyclopentyl)methyl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; (C1-C4)alkyl(C5-C6)cycloalkenyl, where the cycloalkenyl ring is optionally substituted with one -OH group, and / or one or two ether group(s), and / or up to four (i.e., 0, 1, 2, 3 or 4) C1-C7 alkyl groups (e.g., (2,6,6-trimethylcyclohex-1-en-1-yl)ethyl, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-3-yl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; (C2-C3)alkenyl(C5-C6)cycloalkenyl, where the cycloalkenyl ring contains one -OH group, and / or one or two ether group(s), and / or up to four (i.e. 0, 1, 2, 3 or 4) C1-C7 alkyl groups (e.g. (2,6,6-trimethylcyclohex-1-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-ene-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)prop-2-en-2-yl, (2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-2-yl), C2-C7 alkenyl (e.g. isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl, optionally substituted; C6~C 14 Aryl, e.g. phenyl or naphthyl; C6~C 14 Aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 11 (where R 11 is independently substituted with up to three (i.e., 0, 1, 2, or 3) groups selected from hydrogen and C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl); (C1-C4) Alkyl(C6-C 14) Aryl, e.g. benzyl, 2-phenylethyl; (C1-C4) alkyl (C6-C 14 ) aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 12 (where R 12 is independently substituted with up to two groups (for example, one group) selected from hydrogen and C1-C4 alkyl (for example, ethyl, iso-propyl, tert-butyl); (C2-C8) Alkenyl (C6-C 14 ) Aryl, for example 2-phenylethylen-1-yl, 1-phenylhept-1-en-2-yl; (C2-C8) Alkenyl (C6-C 14 ) aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 13 (where R 13 is independently substituted with up to two groups (for example, one group) selected from hydrogen and C1-C4 alkyl (for example, ethyl, iso-propyl, tert-butyl); C8~C 12 It contains carbon atoms and may optionally have one C-C double bond, and is selected from the group consisting of C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 14 (where R 14 is a bicyclic or tricyclic hydrocarbon ring, optionally substituted with up to six groups independently selected from hydrogen and C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl); is selected from the group consisting of R2 is selected from the group consisting of hydrogen, C1-C5 alkyl, and C2-C5 alkenyl; or R1 and R2 taken together with the carbon atoms to which they are attached form a 5-16 membered hydrocarbon ring, which ring may be optionally substituted with a C1-C5 alkyl group (e.g., methyl, 3-methylbutyl, pentyl), or an alkylacetate group, for example, R1 and R2 taken together with the carbon atoms to which they are attached form 3-(2-methoxy-2-oxoethyl)-2-pentylcyclopent-1-ylidene, cyclopentadecylidene; R3 is Straight or branched C1-C 15 Alkyl, e.g., C5-C such as methyl, ethyl, propyl, isopropyl, 2-butyl, 2-methylpentyl, octyl, decyl, dodecyl, 2-methylundecyl, etc. 14 , Straight or branched C2-C 15 Alkenyl, e.g., C5-C such as 3-methylbut-2-en-1-yl 14 ; Optionally substituted C3-C8 cycloalkyl, such as cyclobutyl, cyclopentyl, cyclohexyl, 2-isopropyl-5-methylcyclohexyl, cycloheptyl, cyclooctyl, C8~C 12 Bicyclic or tricyclic hydrocarbon rings containing carbon atoms, for example (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl (myrtenyl); and aromatic residues selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl, is selected from the group consisting of The above uses are provided.

[0017] The configuration of the C-N double bond in the compound of formula (I) is not specified and therefore it has either the E- or Z-configuration, or the compound is a mixture of the E and Z isomers.

[0018] In R1, R2 and / or R3, each double bond can have either the E- or Z-configuration or be an E- / Z-mixture, unless further specified.

[0019] Apart from the ketone or aldehyde of formula (II), the compound of formula (I) further releases a nitrogen-containing compound, such as an oxime (compound of formula (III)) or a nitrile (compound of formula (IV)), or a fragment thereof. [ka]

[0020] In the compounds of formula (III), R4 and R5 together with the carbon atom to which they are attached form the residue R3 as defined for the compounds of formula (I) above.

[0021] In the compounds of formula (IV), R6 together with the carbon atom to which it is attached forms a residue R3 as defined for the compounds of formula (I) above.

[0022] Some subgroups of nitrones have been reported in the literature. For example, according to EP0311568, long-chain N-alkyl-α-alkyl nitrones can be used as process stabilizers for organic materials. In US2004198926A1, the use of vanillin nitrones as hardeners for phenolic resins is described. However, the use of nitrones as fragrance precursors is not disclosed.

[0023] According to one aspect of the present invention, there is provided the use of a compound of formula (I) as a precursor, wherein R1 and R2 are as defined above and R3 is selected from the group consisting of isopropyl, cyclohexyl, benzyl and p-methylbenzyl.

[0024] For example, (E)-N-isopropyl-2-methylundecane-1-imine oxide, 2-methyl-N-(4-methylbenzyl)undecane-1-imine oxide, N-cyclohexyl-2-methylundecane-1-imine oxide, N-benzylnona-2,6-diene-1-imine oxide, (2E,3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-ene-2-imine oxide, 2-methyl-N-(3-methyl N-cyclobutyl-2-methylundecane-1-imine oxide, N-(furan-2-ylmethyl)-2-methylundecane-1-imine oxide, N,2-dimethylundecane-1-imine oxide, N-benzyl-2-methylundecane-1-imine oxide, N-ethyl-2-methylundecane-1-imine oxide, 2-methyl-N-(2-methylpentyl)undecane-1-imine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylundecane-1-imine oxide, N-(3-ethoxy-4-hydroxybenzyl)-2-methylundecane-1-imine oxide, 2-methyl-N-(naphthalen-2-ylmethyl)undecane-1-imine oxide, 2-methyl-N-(2-methylundecyl)undecane-1-imine oxide, N-(4-methoxybenzyl)-2-methylundecane-1-imine oxide, N-(s ec-butyl)-2-methylundecane-1-imine oxide, 2-methyl-N-phenylundecane-1-imine oxide, N-cyclopentyl-2-methylundecane-1-imine oxide, 2-methyl-N-(4-nitrobenzyl)undecane-1-imine oxide, N-(cyclohexylmethyl)-2-methylundecane-1-imine oxide, N-(4-isopropylbenzyl)-2-methylundecane-1-imine oxide, N-(((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-2-methylundecane-1-imine oxide, N-(2-isopropyl-5-methylcyclohexyl)-2-methylundecane-1-imine oxide, 2-methyl-N-(1-phenylethyl)undecane-1-imine oxide, N-(sec-butyl)-2-methylundecane-1-imine oxide, 2-methyl-N-octylundecane-1-imine oxide, N-cycloheptyl-2-methylundecane-1-imine oxide, 2-methyl-N-(pyridin-2-ylmethyl)undecane-1-imine oxide, N-cyclooctyl-2-methylundecane-1-imine oxide, 2-methyl-N-(1-( Naphthalen-2-yl)ethyl)undecane-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-methylpropan-1-imine oxide, N-benzyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, N-ethyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(4-methoxybenzyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-isopropylpropan-1-imine oxide, N-cyclohexyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(1-(naphthalen-2-yl)ethyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(2-methylundecyl)propan-1-imine oxide, N-(sec-butyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N -(1-phenylethyl)propan-1-imine oxide, N-cyclobutyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(3-methylbut-2-en-1-yl)propan-1-imine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-methylmethanimine oxide, N-benzyl-1-(3-ethoxy-4-hydroxyphenyl)methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N- Ethyl methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-(4-methoxybenzyl) methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-isopropyl methanimine oxide, N-cyclohexyl-1-(3-ethoxy-4-hydroxyphenyl) methanimine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-1-(3-ethoxy-4-hydroxyphenyl) methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N -(1-(naphthalen-2-yl)ethyl)methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-(2-methylundecyl)methanimine oxide, N-isopropyl-4-(4-methoxyphenyl)butan-2-imine oxide, N-isopropyldodecane-1-imine oxide, 7-hydroxy-N-isopropyl-3,7-dimethyloctan-1-imine oxide, 3-(4-isobutylphenyl)-N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyl-2,6-Dimethylhept-5-en-1-imine oxide, N-isopropyl-2-methyldecane-1-imine oxide, 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-isopropylmethanimine oxide, 4-(4-hydroxyphenyl)-N-isopropylbutan-2-imine oxide, N-isopropyl-3,5,5-trimethylhexane-1-imine oxide, N-isopropyldec-9-en-1-imine oxide; N-isopropyl-3-(3-isopropylphenyl)butan-1-imine oxide, 3-(4-(tert-butyl)phenyl)-N-isopropylpropan-1-imine oxide, N-isopropyl-1-(naphthalen-2-yl)ethane-1-imine oxide, N-isopropyl-3-methylbutan-1-imine oxide, N-isopropyl-3,7-dimethyloct-6-en-1-imine oxide, N-isopropyl -2,4,7-trimethyloct-6-en-1-imine oxide, N-isopropyl-1-(1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methanimine oxide, 1-(2,4-dimethylcyclohex-3-en-1-yl)-N-isopropylmethanimine oxide, N-isopropyl-3-(4-isopropylphenyl)-2-methylpropan-1-imine oxide, (2E)-N-isopropyl Propyl-3,7-dimethylocta-2,6-dien-1-imine oxide, (2E)-N-isopropylhex-2-en-1-imine oxide, (2E,6E)-N-isopropyl-3,7,11-trimethyldodeca-2,6,10-trien-1-imine oxide, N-isopropyl-1-(8-isopropyl-6-methylbicyclo[2.2.2]oct-5-en-2-yl)methanimine oxide; 1-(8,8-di Methyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(2,4,6-trimethylcyclohex-3-en-1-yl)methanimine oxide, N-isopropyl-4-(4-methoxyphenyl)butan-2-imine oxide, N-isopropyl-2-phenylethane-1-imine oxide, 9-hydroxy-N-isopropyl-5,9-Dimethyldec-4-en-1-imine oxide, 1-(3-hydroxy-4-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-isopropylphenyl)methanimine oxide, (S)-N-isopropyl-1-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanimine oxide, N-isopropyloctan-1-imine oxide, (3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide oxide, N-isopropyl-3-(2-methoxy-2-oxoethyl)-2-pentylcyclopentan-1-imine oxide, (2E)-N-isopropyldodec-2-en-1-imine oxide, 3-(3-ethylphenyl)-N-isopropyl-2,2-dimethylpropan-1-imine oxide, N-isopropyl-3-(3-methoxyphenyl)-2-methylpropan-1-imine oxide, N-isopropyl-3-(methylthio)propan-1-imine oxide, 3-(4-(tert-butyl)phenyl)-N-isopropyl-2-methyl N-isopropyl-7-methoxy-3,7-dimethyloctan-1-imine oxide, N-isopropyl-1-(3-methylbenzofuran-2-yl)ethane-1-imine oxide, 4-(hexyloxy)-N-isopropylbutan-1-imine oxide, (4Z)-N-isopropylhept-4-en-1-imine oxide, 3-(benzo[d][1,3]dioxol-5-yl)-N-isopropyl-2-methylpropan-1-imine oxide, (R)-N-isopropyl-2-(2,2,3-trimethyl)propan-1-imine oxide 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-methylmethanimine oxide, N-benzyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide, 9-hydroxy-N,5,9-trimethyldec-4-en-1-imine oxide, N-benzyl-9-hydroxy-5,9-dimethyldec-4-en-1-imine oxide, (3E)-N-benzyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide, (3Z)-N-benzylhex-3-en-1-imine oxide, N-benzyl-4-(hexyloxy)butan-1-imine oxide, N-benzyl-4-((6-methylheptan-2-yl)oxy)butan-1-imine oxide, (4Z)-N-benzylhept-4-en-1-imine oxide, N-benzyl-2-((3,7-dimethyloct-6-en-1-yl)oxy)ethane-1-imine oxide oxide, (2E,6Z)-N-benzylnona-2,6-dien-1-imine oxide, N-(3-ethoxy-4-hydroxybenzyl)-1-(furan-2-yl)methanimine oxide, (2E)-N-benzyldodec-2-en-1-imine oxide, (2E)-N-benzyloct-2-en-1-imine oxide, (2E,6E)-N-benzyl-3,7-dimethylnona-2,6-dien-1-imine oxide, (2E)-N-benzyl-2-methyl-3-phenylprop-2-en-1-imine oxide amine oxide, (2E)-N-benzyl-3,7-dimethylocta-2,6-dien-1-imine oxide, (2E)-N-benzylnon-2-en-1-imine oxide, 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-(2-methylundecyl)methanimine oxide, 7-hydroxy-3,7-dimethyl-N-(2-methylundecyl)octan-1-imine oxide, (4E)-N-cyclohexyl-9-hydroxy-5,9-dimethyldeca- 4-ene-1-imine oxide, N-cyclohexyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide, N-benzyl-3-(3-isopropylphenyl)butan-1-imine oxide, N-benzyl-4-(4-hydroxyphenyl)butan-2-imine oxide, N-benzyl-2-methyldecane-1-imine oxide, N-benzyl-7-hydroxy-3,7-dimethyloctan-1-imine oxide, 3-(benzo[d][1,3]dioxol-5-yl)-N-benzyl-2-methylpropan-1-imine oxide, N-(2-methylundecyl)propan-1-imine oxide, N-benzyldec-9-en-1-imine oxide, 1-(4-hydroxy-3-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-methoxyphenyl)methanimine oxide, N-isopropylnonan-1-imine oxide, 1-(benzo[d][1,3]dioxol-5-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(p-tolyl)methanimine The present invention provides the use of a compound of formula (I) as a precursor selected from the group consisting of N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyl-1-(3,4-dimethoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyldecane-1-imine oxide, N-isopropylhexan-1-imine oxide, 1-(furan-2-yl)-N-isopropylmethanimine oxide, N-benzyl-1-(4-methoxyphenyl)methanimine oxide, N-benzyldodecane-1-imine oxide and N-decyldecane-1-imine oxide.

[0025] The compound represented by formula (I) above, when exposed to ambient air and / or humidity (by oxidation and / or hydrolysis), releases volatile compounds over a long period of time (e.g., several days, such as 2-7 days, or even longer). In one embodiment, at least one of the compounds released is a fragrance compound. For example, the compound represented by formula (II) is a fragrance aldehyde (for R2=H) or ketone (for R2≠H).

[0026] For example, fragrant aldehydes (for R2=H) or ketones (for R2≠H) represented by formula (II) that can be released from compounds represented by formula (I) upon exposure to ambient air and / or humidity include 2-methylundecanal, 3-(4-isobutyl-2-methylphenyl)propanal, 3-ethoxy-4-hydroxybenzaldehyde, 4-(4-methoxyphenyl)butan-2-one, dodecanal, 4-hydroxy-3-methoxybenzaldehyde (vanillin), 4-methoxybenzaldehyde (anisaldehyde), 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal), 3-(4-isobutylphenyl)propanal, 3-ethoxy-4-hydroxybenzaldehyde, 4-(4-methoxyphenyl)butan-2-one, dodecanal, 4-hydroxy-3-methoxybenzaldehyde (vanillin), 4-methoxybenzaldehyde (anisaldehyde), 7-hydroxy-3,7-dimethyloctanal (hydroxycitronellal), 3-(4-isobutylphenyl)propanal, 3-(4-methyl ... )-2-Methylpropanal (Silvial), 2,6-Dimethylhept-5-enal (Melonal), 2-Methyldecanal, 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (Cyclohexal), 4-(4-hydroxyphenyl)butan-2-one (Raspberry ketone), 3,5,5-Trimethylhexanal (Isononilic aldehyde), Nonanal, Dec-9-enal, 3-(3-isopropylphenyl)butanal (Florhydral), 3-(4-(tert-butyl)phenyl)propanal (Burgeonal), 1-(Naphthalen-2-yl)ethan-1-one (Orange Crist), 3-Methylbutanal, 3,7-Dimethyloct-6-enal (Citronellal), 2,4,7-Trimethyloct-6-enal (Pomelol), 1-Methyl-2-(5-methylhex-4-en-2-yl)cyclopropane-1-carbaldehyde (Rosyfolia), 2,4-Dimethylcyclohex-3-ene-1-carbaldehyde, 3-(4-Isopropylphenyl)-2-methylpropanal (Cyclamen aldehyde ), (E)-3,7-dimethylocta-2,6-dienal (citral), benzo[d][1,3]dioxole-5-carbaldehyde (heliotropine), hex-2-enal, (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal (farnesal), 8-isopropyl-6-methylbicyclo[2.2.2]oct-5-ene-2-carbaldehyde (cyclomyral), 8,8-dimethyl-1,2,3,4,5,6,7,8-Octahydronaphthalene-2-carbaldehyde (Maceal), 2,4,6-Trimethylcyclohex-3-ene-1-carbaldehyde (Isocyclocitral), 4-Methylbenzaldehyde, 3,4-Dimethoxybenzaldehyde (Veratrylaldehyde), 4-(4-Methoxyphenyl)butan-2-one, 2-Phenylacetaldehyde, 9-Hydroxy-5,9-Dimethyldec-4-enal (Mahonial), 3-Hydroxy-4-Methoxybenzaldehyde, 4-Isopropylbenzaldehyde (Cuminaldehyde), Isobutyraldehyde, (S)-4-(Prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde (Egomaldehyde), Decanal, Octanal, Hexanal, (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one (β-ionone), Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione), (E)-Dodec-2-enal (Mandarinaldehyde), 3-(3-ethylphenyl)-2,2-dimethylpropanal (Floral Ozone), 3-(3-methoxyphenyl)-2-methylpropanal, 3-(methylthio)propanal (methional), 3-(4-(tert-butyl)phenyl)-2-methylpropanal (Lilial), 7-methoxy-3,7-dimethyloctanal, 3-methyl-2-(prop-1-en-2-yl)benzofuran, 4-(hexyloxy)butanal, (Z)-hept-4-enal, furan-2-carbaldehyde, 3-(benzo[d][1,3]dioxol-5-yl)-2-methylpropanal, (R)-2 -(2,2,3-trimethylcyclopent-3-en-1-yl)acetaldehyde, (Z)-hex-3-enal, 4-((6-methylheptan-2-yl)oxy)butanal, (Z)-hept-4-enal, 2-((3,7-dimethyloct-6-en-1-yl)oxy)acetaldehyde, (2E,6Z)-nona-2,6-dienal, (E)-oct-2-enal, (2E,6E)-3,7-dimethylnona-2,6-dienal, (E)-2-methyl-3-phenylacrylaldehyde, (E)-3,7-dimethyloct-2,It may be selected from the group consisting of 6-dienal, non-2-enal, 7-hydroxy-3,7-dimethyloctanal and 2-methyldecanal.

[0027] Furthermore, the fragrant aldehydes (for R2=H) or ketones (for R2≠H) represented by formula (II) which can be released from the compounds represented by formula (I) upon exposure to ambient air and / or humidity include benzaldehyde, 2,6,10-trimethylundec-9-enal, 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-naphthalene-2-carbaldehyde, (4-isopropyl-phenyl)-ethanal, 2,4-dimethyl-cyclohex-3-ene-1-carbaldehyde, 1,3,5-trimethyl ... Cyclohex-1-ene-4-carbaldehyde, 4-(4-hydroxy-4-methylpentyl)-cyclohex-3-ene-1-carbaldehyde, hex-2-enal, hex-3-enal, 3-(3-tert-butylcyclohexyl)propanal, 2-(4-tert-pentylcyclohexyl)acetaldehyde, 3,5,5-trimethyl-hexanal, heptanal, 2,6-dimethyl-hept-5-enal, dec-4-en-1-al, 2-methyl-decanal, undec-10-en-1-al, undecanal, tridecane aldehyde, tridec-2-enal, undec-9-enal, 2-phenyl-propanal, 2-(4-methyl-phenyl)-ethanal, 2-(4-methoxyphenyl)acetaldehyde, 3,7-dimethyl-octanal, dihydrofarnesal (3,7,11-trimethyldodec-6,10-dienal), 7-hydroxy-3,7-dimethyl-octanal, 2,6-dimethyl-oct-5-en-1-al, 4-(4-methyl-pent-3-enyl)-cyclohex-3-ene-1-carbaldehyde, 2,3,5,5,-tetramethyl -Hexanal, Decahydro-4,8,8-trimethyl-1,4-methanoazulene-9-carboxaldehyde (longifolic aldehyde), 3-(4-tert-butyl-phenyl)-propanal, 3-(4-isobutyl-phenyl)-propanal, 3-(benzo[1,3]dioxol-5-yl)-2-methyl-propanal, 3,7-dimethyl-oct-6-en-1-al, 2-methyl-3-(4-isopropylphenyl)-propanal, 4-tert-butyl-cyclohexane-1-carbaldehyde, 4-(octahydro-4,7-Methano-5H-inden-5-ylidene)-butanal, (3,7-dimethyl-oct-6-enyloxy)-ethanal, 2(E),6(Z)-nonadienal, 2,4-dimethyl-2,6-heptadienal, (E)-deca-2-enal, dodeca-2-enal, 3,7-dimethyl-octa-2,6-dienal, 2,4-diethyl-hepta-2,6-dienal, 3,7-dimethyl-nona-2,6- Dienal, 2-propyl-hept-2-enal, 3-(4-methoxyphenyl)-2-methylpropanal, 1,3-benzodioxole-5-carboxaldehyde, 2,6,6-trimethylcyclohexa-1,3-dienecarbaldehyde, 4-((6-methylheptan-2-yl)oxy)butanal, 3-(4-ethylphenyl)-2,2-dimethylpropanal, (E)-2-benzylideneheptanal , Cinnamaldehyde, 3-(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)propanal, 2-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)butanal (Cetonal), 4-Isopropenyl-cyclohex-1-ene-1-carbaldehyde, alpha-ionone, dihydro alpha-ionone, dihydro beta-ionone, N-allyl alpha-ionone ionone (1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,6-heptadiene-3-one), N-methyl alpha-ionone (1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one), dimethyl alpha-ionone (2-methyl-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one), and Cetone Further ionones such as Alpha (3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one), Nectaryl (2-(2-(4-methylcyclohex-3-en-1-yl)propyl)cyclopentanone), Magnolion (3-(2-oxopropyl)-2-pentylcyclopentanone), Acetophenone and Cassione (4-(benzo[d][1,3]dioxol-5-yl)butan-2-one).

[0028] For example, a fragrant aldehyde (for R2=H) or ketone (for R2≠H) represented by formula (II) that can be released from a compound represented by formula (I) upon exposure to ambient air and / or humidity is a compound having at least 4 or more carbon atoms, for example at least 6 or more carbon atoms.

[0029] Exposure of the precursor compound to ambient air means exposure to molecular oxygen, which can cause cleavage of the compound of formula (I) and release of the compound of formula (II). The concentration of oxygen in air is sufficient to cleave the compound of formula (I), so that the cleavage products can be detected in the ambient air, for example by olfaction or GC-MS analysis of headspace samples.

[0030] Exposure of the precursor compound to humidity means exposure to water that may cause cleavage of the compound of formula (I) and release of the compound of formula (II). Traces of water are already sufficient to allow cleavage of the compound of formula (I).

[0031] The compounds of formula (I) are extremely stable when not exposed to ambient air or humidity, i.e. when stored in pure form in a suitable container protected from air and humidity, or when stored in a suitable solvent, e.g. dipropylene glycol, isopropyl myristate, triethyl citrate, or when incorporated into consumer products such as detergents, shampoos and fabric conditioners. Thus, the compounds of formula (I) may find use in a wide range of consumer products where sustained and defined release of fragrance compounds is desired. In some embodiments, a stabilizing compound, e.g. tocopherol, may be added to the compounds of formula (I), e.g. 0.01-0.5% by weight.

[0032] For example, the compounds of formula (I) can serve as fragrance precursors in consumer products, such as fabric care, personal care and home care products, or in fine fragrances. In particular, these precursors are well suited for fabric care applications.

[0033] The personal care products that the compound of formula (I) can be added to include, for example, all kinds of body care products.Products of particular interest are hair care products, such as shampoos, conditioners, and hairsprays, and skin care products, such as lotions or creams.Furthermore, the compound of formula (I) can be added to soaps, bath and shower gels, and deodorants.

[0034] The home cleaning products to which the compound represented by formula (I) can be added include all kinds of detergents, window cleaners, hard surface cleaners, multi-purpose cleaners and furniture polishes.Preferably the product is a liquid, for example a fabric conditioner composition.Substrates such as fabrics treated with the product containing the compound represented by formula (I) emit a fresh and / or clean smell under cutting conditions for much longer than those treated with conventional products.Fabrics or clothes washed with such fabric softeners still exhibit noticeable fragrance release after one week.

[0035] For example, compounds of formula (I) may serve as fragrance precursors in consumer products which further comprise an enzyme.

[0036] The compound of formula (I) may be employed in the consumer product base by simply mixing the compound of formula (I) or a fragrance composition comprising the compound of formula (I) directly with the consumer product base, or it may be encapsulated at an earlier stage with the supplemental material, for example using polymers, capsules, microcapsules and nanocapsules, liposomes, membrane-forming agents, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, and then mixed with the consumer product base.

[0037] Thus, the present invention provides a method of producing a fragranced article which involves the incorporation of a compound of formula (I) as a fragrance ingredient, either by directly incorporating it into a consumer product base, or by incorporating a fragrance composition comprising a compound of formula (I), which can then be mixed with a consumer product base using conventional techniques and methods.

[0038] The present invention also provides the following: a) a compound of formula (I) or a mixture containing it as an odorant; and b) Consumer product base Fragranced articles are also provided, including:

[0039] As used herein, "consumer product base" means a composition for use as a consumer product to perform a specific function, such as cleaning, softening, and care, or the like.

[0040] The compounds of formula (I) can be used alone, in their mixtures or in combination with other fragrance ingredients and / or their precursors, such as those described, for example, in "Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 2003, and include fragrance compounds and essential oils of natural or synthetic origin.

[0041] The amount in which the compound of formula (I) may be incorporated into the various above-mentioned products varies within a wide range. The amount depends on the nature of the fragrance compound to be released, the nature of the product to which the compound of formula (I) is added, and the desired olfactory effect. The amount used also depends on the co-ingredients in a given composition when the compound of formula (I) is used in admixture with a perfumed co-ingredient, solvent or adjuvant. Typical concentrations are 0.0001 to 5 percent by weight of the article. In one embodiment, the compound of the present invention may be employed in a fabric softener in an amount of 0.0001 to 0.2 percent by weight. In another embodiment, the compound of the present invention may be used in a liquid detergent in an amount of 0.001 to 0.5 percent by weight (for example, up to about 5 percent by weight), more preferably between 0.02 to 4 percent by weight. In another embodiment, the compound of the present invention may be used in a shampoo in an amount of 0.001 to 0.5 percent by weight. However, these values ​​are given only as an example, since the skilled perfumer may also achieve effects or create new accords at lower or higher concentrations.

[0042] Some of the compounds according to formula (I) are known from different uses, however, the majority of the compounds are novel.

[0043] Thus, the present invention relates to a compound of formula (I) [ka] A ketone or aldehyde represented by formula (II) [ka] As a precursor for producing During the ceremony R1 is, Straight or branched C1-C 15 Alkyl, e.g., C6, C7, C8, C9, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Alkyl; Straight or branched C1-C 15 Hydroxyalkyl, alkoxyalkyl and alkylthioalkyl, for example, C6, C7, C8, C9, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Hydroxyalkyl, 4-(hexyloxy)butyl, 3-(methylthio)propyl; Straight or branched C2-C 15 Alkenyl, e.g., C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C210, C22, C30, C41, C51, C61, C72, C81, C92, C19, C23, C34, C45, C46, ​​C47, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Alkenyl; Straight or branched C2-C 15 Hydroxyalkenyl, e.g., C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C210, C220, C23, C24, C25, C36, C37, C38, C39, C40, C41, C42, C43, C44, C 10 , C 11 , C 12 or C 13 C5~C etc. 14 Hydroxyalkenyl; C3-C8 cycloalkyl, such as cyclopentyl or cyclohexyl; C3-C8 cycloalkyl (e.g., cyclopentyl or cyclohexyl) substituted with one, two, or three groups selected from C1-C7 alkyl (e.g., ethyl, isopropyl, tert-pentyl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; C5-C8 cycloalkenyl (e.g. cyclopent-3-enyl, cyclohex-1-enyl, cyclohexa-2,4-dienyl, cyclooct-3-enyl); C5-C8 cycloalkenyl (e.g. cyclohex-1-enyl, cyclohex-2,4-dienyl, cyclooct-3-enyl) substituted with one, two or three groups selected from C1-C7 alkyl (e.g. ethyl, isopropyl, tert-pentyl), C2-C7 alkenyl (e.g. isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl and C3-C5 cycloalkyl (e.g. R1 is 7-methyl-spiro[4.5]dec-8-en-6-yl, spiro[4.5]dec-7-en-7-yl, 5,5-dimethylcyclohex-1-enyl, 2,6,6-trimethylcyclohex-1,3-dienyl, 2,4-dimethylcyclohex-3-enyl, or 4-isopropenyl (cyclohex-1-en-1-yl)); (C1-C3)alkyl(C5-C6)cycloalkyl, where the cycloalkyl ring is optionally substituted with one group selected from -OH and =O groups, and / or one or two ether group(s), and / or up to four C1-C7 alkyl groups (e.g., R1 is (3-tertbutylcyclohexyl)ethyl, or (4-(1,1-dimethylpropyl)cyclohexyl)methyl, (3-oxo-2-pentylcyclopentyl)methyl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; (C1-C4)alkyl(C5-C6)cycloalkenyl, where the cycloalkenyl ring is optionally substituted with one -OH group, and / or one or two ether group(s), and / or up to four (i.e., 0, 1, 2, 3 or 4) C1-C7 alkyl groups (e.g., (2,6,6-trimethylcyclohex-1-en-1-yl)ethyl, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-3-yl), C2-C7 alkenyl (e.g., isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; (C2-C3)alkenyl(C5-C6)cycloalkenyl, where the cycloalkenyl ring contains one -OH group, and / or one or two ether group(s), and / or up to four (i.e. 0, 1, 2, 3 or 4) C1-C7 alkyl groups (e.g. (2,6,6-trimethylcyclohex-1-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-ene-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)prop-2-en-2-yl, (2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-2-yl), C2-C7 alkenyl (e.g. isopropenyl), C1-C7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl, optionally substituted; C6~C 14 Aryl, e.g. phenyl or naphthyl; C6~C 14 Aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 11 (where R 11 is independently substituted with up to three (i.e., 0, 1, 2, or 3) groups selected from hydrogen and C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl); (C1-C4) Alkyl(C6-C 14) Aryl, e.g. benzyl, 2-phenylethyl; (C1-C4) alkyl (C6-C 14 ) aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 12 (where R 12 is independently substituted with up to two groups (for example, one group) selected from hydrogen and C1-C4 alkyl (for example, ethyl, iso-propyl, tert-butyl); (C2-C8) Alkenyl (C6-C 14 ) Aryl, for example 2-phenylethylen-1-yl, 1-phenylhept-1-en-2-yl; (C2-C8) Alkenyl (C6-C 14 ) aryl, where the aryl ring is C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 13 (where R 13 is independently substituted with up to two groups (for example, one group) selected from hydrogen and C1-C4 alkyl (for example, ethyl, iso-propyl, tert-butyl); C8~C 12 It contains carbon atoms and may optionally have one C-C double bond, and is selected from the group consisting of C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl), -O-CH2-O-, and -OR 14 (where R 14 is a bicyclic or tricyclic hydrocarbon ring, optionally substituted with up to six groups independently selected from hydrogen and C1-C4 alkyl (e.g., ethyl, iso-propyl, tert-butyl); is selected from the group consisting of R2 is selected from the group consisting of hydrogen, C1-C5 alkyl, and C2-C5 alkenyl; or R1 and R2 together with the carbon atoms to which they are attached form a 5-16 membered hydrocarbon ring, which ring may be optionally substituted with a C1-C5 alkyl group (e.g., methyl, 3-methylbutyl, pentyl), or an alkylacetate group, for example, R1 and R2 together with the carbon atoms to which they are attached form 3-(2-methoxy-2-oxoethyl)-2-pentylcyclopent-1-ylidene, cyclopentadecylidene; R3 is Straight or branched C1-C 15 Alkyl, e.g., C5-C such as methyl, ethyl, propyl, isopropyl, 2-butyl, 2-methylpentyl, octyl, decyl, dodecyl, 2-methylundecyl, etc. 14 , Straight or branched C2-C 15 Alkenyl, e.g., C5-C such as 3-methylbut-2-en-1-yl 14 ; Optionally substituted C3-C8 cycloalkyl, such as cyclobutyl, cyclopentyl, cyclohexyl, 2-isopropyl-5-methylcyclohexyl, cycloheptyl, cyclooctyl, C8~C 12 Bicyclic or tricyclic hydrocarbon rings containing carbon atoms, for example (1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl (myrtenyl); and aromatic residues selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl; Selected from the group consisting of: However, the compound is not particularly limited to 1-(4-hydroxy-3-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-methoxyphenyl)methanimine oxide, N-isopropylnonan-1-imine oxide, 1-(benzo[d][1,3]dioxol-5-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(p-tolyl)methanimine oxide, 1-(3,4-dimethoxyphenyl)-N-isopropylmethanimine oxide, The compound is not N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyldecane-1-imine oxide, N-isopropylhexane-1-imine oxide, 1-(furan-2-yl)-N-isopropylmethanimine oxide, N-benzyl-1-(4-methoxyphenyl)methanimine oxide, N-benzyldodecane-1-imine oxide, or N-decyldecane-1-imine oxide.

[0044] The configuration of the C-N double bond in the compound of formula (I) is not specified and therefore it has either the E- or Z-configuration, or the compound is a mixture of the E and Z isomers.

[0045] In R1, R2 and / or R3, each double bond can have either the E- or Z-configuration or be an E- / Z-mixture, unless further specified.

[0046] For example, the compound represented by formula (I) is (E)-N-isopropyl-2-methylundecane-1-imine oxide, 2-methyl-N-(4-methylbenzyl)undecane-1-imine oxide, N-cyclohexyl-2-methylundecane-1-imine oxide, N-benzylnona-2,6-diene-1-imine oxide, (2E,3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide, N-cyclobutyl-2-methylundecane-1-imine oxide, N-(furan-2-ylmethyl)-2-methylundecane-1-imine oxide, N,2-dimethylundecane-1-imine oxide, N-benzyl-2-methylundecane-1-imine oxide, N-ethyl-2-methylundecane-1-imine oxide, 2-methyl-N-(2 -methylpentyl)undecane-1-imine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylundecane-1-imine oxide, N-(3-ethoxy-4-hydroxybenzyl)-2-methylundecane-1-imine oxide, 2-methyl-N-(naphthalen-2-ylmethyl)undecane-1-imine oxide, 2-methyl-N-(2-methylundecyl)undecane-1-imine oxide, N-(sec-butyl )-2-methylundecane-1-imine oxide, 2-methyl-N-phenylundecane-1-imine oxide, N-cyclopentyl-2-methylundecane-1-imine oxide, 2-methyl-N-(4-nitrobenzyl)undecane-1-imine oxide, N-(cyclohexylmethyl)-2-methylundecane-1-imine oxide, N-(4-isopropylbenzyl)-2-methylundecane-1-imine oxide, N-(((1R,5S)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-2-methylundecane-1-imine oxide, N-(2-isopropyl-5-methylcyclohexyl)-2-methylundecane-1-imine oxide, 2-methyl-N-(1-phenylethyl)undecane-1-imine oxide, N-(sec-butyl)-2-methylundecane-1-imine oxide, 2-methyl-N-octylundecane-1-imine oxide, N-cycloheptyl-2-methylundecane-1-imine oxide, 2-methyl-N-(pyridin-2-ylmethyl)undecane-1-imine oxide, N-cyclooctyl-2-methylundecane-1-imine oxide, 2-methyl-N-(1-( Naphthalen-2-yl)ethyl)undecane-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-methylpropan-1-imine oxide, N-benzyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, N-ethyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(4-methoxybenzyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-isopropylpropan-1-imine oxide, N-cyclohexyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(1-(naphthalen-2-yl)ethyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(2-methylundecyl)propan-1-imine oxide, N-(sec-butyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N -(1-phenylethyl)propan-1-imine oxide, N-cyclobutyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide, 3-(4-isobutyl-2-methylphenyl)-N-(3-methylbut-2-en-1-yl)propan-1-imine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-methylmethanimine oxide, N-benzyl-1-(3-ethoxy-4-hydroxyphenyl)methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N- Ethyl methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-(4-methoxybenzyl) methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-isopropyl methanimine oxide, N-cyclohexyl-1-(3-ethoxy-4-hydroxyphenyl) methanimine oxide, N-(benzo[d][1,3]dioxol-5-ylmethyl)-1-(3-ethoxy-4-hydroxyphenyl) methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N -(1-(naphthalen-2-yl)ethyl)methanimine oxide, 1-(3-ethoxy-4-hydroxyphenyl)-N-(2-methylundecyl)methanimine oxide, N-isopropyl-4-(4-methoxyphenyl)butan-2-imine oxide, N-isopropyldodecane-1-imine oxide, 7-hydroxy-N-isopropyl-3,7-dimethyloctan-1-imine oxide, 3-(4-isobutylphenyl)-N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyl-2,6-Dimethylhept-5-en-1-imine oxide, N-isopropyl-2-methyldecane-1-imine oxide, 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-isopropylmethanimine oxide, 4-(4-hydroxyphenyl)-N-isopropylbutan-2-imine oxide, N-isopropyl-3,5,5-trimethylhexane-1-imine oxide, N-isopropyldec-9-en-1-imine oxide; N-isopropyl-3-(3-isopropylphenyl)butan-1-imine oxide, 3-(4-(tert-butyl)phenyl)-N-isopropylpropan-1-imine oxide, N-isopropyl-1-(naphthalen-2-yl)ethane-1-imine oxide, N-isopropyl-3-methylbutan-1-imine oxide, N-isopropyl-3,7-dimethyloct-6-en-1-imine oxide, N-isopropyl -2,4,7-trimethyloct-6-en-1-imine oxide, N-isopropyl-1-(1-methyl-2-(5-methylhex-4-en-2-yl)cyclopropyl)methanimine oxide, 1-(2,4-dimethylcyclohex-3-en-1-yl)-N-isopropylmethanimine oxide, N-isopropyl-3-(4-isopropylphenyl)-2-methylpropan-1-imine oxide, (2E)-N-isopropyl Propyl-3,7-dimethylocta-2,6-dien-1-imine oxide, (2E)-N-isopropylhex-2-en-1-imine oxide, (2E,6E)-N-isopropyl-3,7,11-trimethyldodeca-2,6,10-trien-1-imine oxide, N-isopropyl-1-(8-isopropyl-6-methylbicyclo[2.2.2]oct-5-en-2-yl)methanimine oxide; 1-(8,8-di Methyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(2,4,6-trimethylcyclohex-3-en-1-yl)methanimine oxide, N-isopropyl-4-(4-methoxyphenyl)butan-2-imine oxide, N-isopropyl-2-phenylethane-1-imine oxide, 9-hydroxy-N-isopropyl-5,9-Dimethyldec-4-en-1-imine oxide, 1-(3-hydroxy-4-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-isopropylphenyl)methanimine oxide, (S)-N-isopropyl-1-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methanimine oxide, N-isopropyloctan-1-imine oxide, (3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide oxide, N-isopropyl-3-(2-methoxy-2-oxoethyl)-2-pentylcyclopentan-1-imine oxide, (2E)-N-isopropyldodec-2-en-1-imine oxide, 3-(3-ethylphenyl)-N-isopropyl-2,2-dimethylpropan-1-imine oxide, N-isopropyl-3-(3-methoxyphenyl)-2-methylpropan-1-imine oxide, N-isopropyl-3-(methylthio)propan-1-imine oxide, 3-(4-(tert-butyl)phenyl)-N-isopropyl-2-methyl N-isopropyl-7-methoxy-3,7-dimethyloctan-1-imine oxide, N-isopropyl-1-(3-methylbenzofuran-2-yl)ethane-1-imine oxide, 4-(hexyloxy)-N-isopropylbutan-1-imine oxide, (4Z)-N-isopropylhept-4-en-1-imine oxide, 3-(benzo[d][1,3]dioxol-5-yl)-N-isopropyl-2-methylpropan-1-imine oxide, (R)-N-isopropyl-2-(2,2,3-trimethyl)propan-1-imine oxide 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-methylmethanimine oxide, N-benzyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide, 9-hydroxy-N,5,9-trimethyldec-4-en-1-imine oxide, N-benzyl-9-hydroxy-5,9-dimethyldec-4-en-1-imine oxide, (3E)-N-benzyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide, (3Z)-N-benzylhex-3-en-1-imine oxide, N-benzyl-4-(hexyloxy)butan-1-imine oxide, N-benzyl-4-((6-methylheptan-2-yl)oxy)butan-1-imine oxide, (4Z)-N-benzylhept-4-en-1-imine oxide, N-benzyl-2-((3,7-dimethyloct-6-en-1-yl)oxy)ethane-1-imine oxide oxide, (2E,6Z)-N-benzylnona-2,6-dien-1-imine oxide, N-(3-ethoxy-4-hydroxybenzyl)-1-(furan-2-yl)methanimine oxide, (2E)-N-benzyldodec-2-en-1-imine oxide, (2E)-N-benzyloct-2-en-1-imine oxide, (2E,6E)-N-benzyl-3,7-dimethylnona-2,6-dien-1-imine oxide, (2E)-N-benzyl-2-methyl-3-phenylprop-2-en-1-imine oxide amine oxide, (2E)-N-benzyl-3,7-dimethylocta-2,6-dien-1-imine oxide, (2E)-N-benzylnon-2-en-1-imine oxide, 1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-(2-methylundecyl)methanimine oxide, 7-hydroxy-3,7-dimethyl-N-(2-methylundecyl)octan-1-imine oxide, (4E)-N-cyclohexyl-9-hydroxy-5,9-dimethyldeca- 4-ene-1-imine oxide, N-cyclohexyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide, N-benzyl-3-(3-isopropylphenyl)butan-1-imine oxide, N-benzyl-4-(4-hydroxyphenyl)butan-2-imine oxide, N-benzyl-2-methyldecane-1-imine oxide, N-benzyl-7-hydroxy-3,7-dimethyloctan-1-imine oxide, 3-(benzo[d][1,3] selected from the group consisting of dioxol-5-yl)-N-benzyl-2-methylpropan-1-imine oxide, N-(2-methylundecyl)propan-1-imine oxide and N-benzyldec-9-en-1-imine oxide.

[0047] The compounds of formula (I) can be prepared starting from the respective fragrant carbonyl compounds of formula (II) as defined above and hydroxylamine (compound of formula (V)). For example, the oxime (compound of formula (III)) is converted in a first step to the corresponding hydroxylamine hydrochloride, which is then reacted with the carbonyl compound (compound of formula (II)) to yield the nitrone (compound of formula (I)).

[0048] [ka]

[0049] In the compounds of formula (III), R4 and R5 together with the carbon atom to which they are attached form the residue R3 as defined for the compounds of formula (I) above.

[0050] For example, the hydroxylamine represented by formula (V) which forms the compound represented by formula (I) together with the compound represented by formula (II) may be N-isopropylhydroxylamine, N-(4-methylbenzyl)hydroxylamine, N-cyclohexylhydroxylamine, N-(3-methylbut-2-en-1-yl)hydroxylamine, N-cyclobutylhydroxylamine, N-(furan-2-ylmethyl)hydroxylamine, N-methylhydroxylamine, N-benzylhydroxylamine, N-ethylhydroxylamine, N-(2-methylpentyl)hydroxylamine, N-(benzo[d][1,3]dioxol-5-ylmethyl)hydroxylamine, N-(3-ethoxy-4-hydroxybenzyl)hydroxylamine, N-(naphthalen-2-ylmethyl)hydroxylamine, N-(2-methylundecyl)hydroxylamine, N-(sec-butyl)hydroxylamine, It may be selected from the group consisting of N-phenylhydroxylamine, N-cyclopentylhydroxylamine, N-(4-nitrobenzyl)hydroxylamine, N-(cyclohexylmethyl)hydroxylamine, N-(4-isopropylbenzyl)hydroxylamine, N-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)hydroxylamine, N-(2-isopropyl-5-methylcyclohexyl)hydroxylamine, N-(1-phenylethyl)hydroxylamine, N-(sec-butyl)hydroxylamine, N-octylhydroxylamine, N-cycloheptylhydroxylamine, N-(pyridin-2-ylmethyl)hydroxylamine, N-cyclooctylhydroxylamine, N-(1-(naphthalen-2-yl)ethyl)hydroxylamine, N-(4-methoxybenzyl)hydroxylamine.

[0051] In some embodiments, hydroxylamine hydrochloride can be obtained from amines via oxidative methods. For example, dialkylamines can be oxidized with H2O2 in the presence of a catalyst to methanimine oxide, which is further converted to the desired hydroxylamine hydrochloride.

[0052] Alternatively, compounds of formula (I) may be prepared in one step directly from hydroxylamine and an aldehyde, provided that the reactivity of the hydroxylamine is sufficient. For example, N-isopropylhydroxylamine can be reacted directly with a carbonyl compound.

[0053] The compounds of formula (I) may be obtained as a solid or in liquid form. In a further aspect, the compounds of the invention are biodegradable as demonstrated by the manometric respirometry test (OECD Guideline for the Testing of Materials No. 301F, Paris 1992).

[0054] The invention will now be further described with reference to the following non-limiting examples. It will be understood that these examples are for the purpose of illustration only, and that variations and modifications may be made by those skilled in the art.

[0055] example General: All reactions were carried out under argon using solvents and reagents from commercial suppliers without further purification. Solvents for extraction and chromatography were of technical grade and used without further purification. Flash chromatography was carried out using Tsingdao Haiyang Chemical silica gel (200-300 mesh) and Santai Technologies silica flash columns. Heptane:MTBE mixtures were used as eluents unless otherwise noted. NMR spectra were recorded on an AW 400 MHz Bruker spectrometer instrument. 1 Chemical shifts for 1 H NMR spectra are reported in δ (ppm) referenced to residual proton signals of deuterated solvents; coupling constants are expressed in Hertz (Hz). 13C NMR spectra were referenced to the carbon signals of the deuterated solvent. The following abbreviations are used: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = double doublet, bs = broad singlet. GC / MS spectral data were obtained from an Agilent 6890 N and MSD 5975 using a column HP-5 MS, 30 m, 0.25 mm, 0.25 μm. High-resolution mass spectra were determined on a Thermo Fisher Scientific LTQ FT Ultra (ESI-MS) and a Waters Micromass GCT Premier (EI-MS).

[0056] Example 1: (E)-2-Methyl-N-(4-methylbenzyl)undecane-1-imine oxide a) 4-Methylbenzaldehyde oxime (215 mmol, 29.00 g, 1 eq) was dissolved in 70 mL MeOH. NaBH3CN (257 mmol, 16.18 g, 1.2 eq) was added in small portions at 0° C. Concentrated HCl (279 mmol, 27.5 g, 1.3 eq) in 50 mL MeOH was added dropwise at 0° C. After the addition, the pH was <4. The reaction was stirred at rt overnight and the pH was still <4. GC and TLC monitoring was used to ensure that no oxime remained. The solvent was removed and the residue was dissolved by adding 10 mL MTBE and 100 mL water. The aqueous layer was saved and then washed with 10 mL MTBE. The aqueous phase was saved and the solvent was removed under vacuum to give the residue (approximately 71.2% pure) as a white solid, which was used in the next step without further purification. The purity of the product was calculated as if it were a mixture of product and NaCl (m / m=1:1.2).

[0057] b) N-(4-methylbenzyl)hydroxylamine hydrochloride (25.27 g, 102 mmol, 1 equiv.) and 112 mL of 10% aqueous sodium hydroxide (45.60 g, 114 mmol, 1.1 equiv.) in water were stirred at rt under argon atmosphere at pH>7 and for another 5 min. Dichloromethane (100 ml) was added to extract the free hydroxylamine, then the organic layers were combined and added dropwise to a mixture of 2-methylundecanal (21.01 g, 114 mmol, 1.1 equiv.) in dichloromethane (100 ml). The mixture was stirred for 2 h at rt. The progress of the reaction was monitored by TLC and GC-MS. After no further conversion was observed, the mixture was dried and the solvent was removed, followed by silica gel chromatography (heptane:MTBE=20:1-0:1) to give (E)-2-methyl-N-(4-methylbenzyl)undecane-1-imine oxide (25.37 g, 82 mmol, 79% yield) as a white solid, which was recrystallized from hexane and DCM (10:1) to give 21.53 g of pure product as a white solid.

[0058] 1 H NMR (400 MHz, CDCl3) δ 7.27 (d, J = 7.7 Hz, 2H), 7.19 (d, J = 7.7 Hz, 2H), 6.42 (d, J = 7.5 Hz, 1H), 4.82 (s, 2H), 3.19 - 2.95 (m, 1H), 2.36 (s, 3H), 1.44 - 1.19 (m, 16H), 1.04 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.7 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 144.03(t), 138.80(q), 130.24(q), 129.68(t), 129.27(t), 69.23(d), 34.12, 31.99, 31.06(t), 29.69(d), 29.63(d), 29.41(d), 27.26(d), 22.78(d), 21.31(s), 16.58(s), 14.21(s). GC / MS (EI): m / z (%): 303 (2) [M + ], 286 (2), 260 (2), 207 (5), 177 (7),161 (18), 105 (100), 77 (13), 55 (12).

[0059] Example 2: (1Z,2E)-N-benzylnon-2-en-1-imine oxide The compound was obtained as a white solid (2.2 mmol, 0.57 g, 47% yield) from N-benzylhydroxylamine hydrochloride (4.7 mmol, 0.75 g, 1 equiv.) and (E)-non-2-enal (5.2 mmol, 0.73 g, 1.1 equiv.) according to the process of Example 1.

[0060] 1 H NMR (400 MHz, CDCl3) δ 7.49 - 7.28 (m, 5H), 6.98 (d, J = 9.4 Hz, 1H), 6.75 (dd, J = 15.9, 9.4 Hz, 1H), 6.30 - 6.08 (m, 1H), 4.88 (s, 2H), 2.32 - 2.08 (m, 2H), 1.48 - 1.35(m, 2H), 1.32 - 1.21(m, 6H), 0.86 (t, J = 6.4 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 143.91(t), 136.51(t), 133.17(q), 129.40(t), 129.06(t), 129.00(t), 121.10(t), 69.05(d), 33.47(d), 31.73(d), 28.97(d), 28.68(d), 22.67(d), 14.18(s). GC / MS (EI): m / z (%): 245 (1) [M+], 229 (5), 186 (6), 172 (15), 144 (22),104 (17), 92 (16), 91 (100), 65 (12).

[0061] Example 3: (E)-N-Cyclohexyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide The compound was obtained from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (24.8 mmol, 5.22 g, 1.1 equiv.) and N-cyclohexylhydroxylamine (22.5 mmol, 2.55 g, 1 equiv.) according to the process of Example 1 as a white solid (6.7 mmol, 2.10 g, 30% yield).

[0062] 1 H NMR (400 MHz, CDCl3) δ 6.59 (d, J = 6.1 Hz, 1H), 5.61 - 5.21 (m, 1H), 3.79 - 3.45 (m, 1H), 3.32 - 2.99 (m, 1H), 2.40 - 2.15 (m, 1H), 2.08 - 1.79 (m, 12H), 1.70 - 1.38 (m, 7H), 1.34 - 1.26 (m, 2H), 1.23 - 1.16 (m, 7H). 13C NMR (101 MHz, CDCl3) δ 140.22(t), 137.74(q), 119.07(t), 73.96(t), 70.91(q), 43.45(d), 38.04(d), 31.23(d), 31.13(d), GC / MS (EI): m / z (%): 307 (1) [M+], 287 (29), 258 (25), 190 (30), 186 (62),130 (68), 117 (100), 91 (81), 59 (80).

[0063] Example 4: (E)-N-Benzyl-2-methylundecane-1-imine oxide The compound was obtained as a white solid (11.2 mmol, 3.48 g, 88% yield) from 2-methylundecanal (14.1 mmol, 2.59 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (12.8 mmol, 2.10 g, 1 equiv.) according to the process of Example 1.

[0064] 1 H NMR (400 MHz, CDCl3) δ 7.49 - 7.29 (m, 5H), 6.48 (d, J = 7.5 Hz, 1H), 4.86 (s, 2H), 3.18 - 2.95 (m, 1H), 1.58 - 1.11 (m, 16H), 1.05 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.7 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 144.20(t), 133.25(q), 129.06(t), 128.88(t), 128.78(t), 69.41(d), 34.02(d), 31.89(d), 31.00(t), 29.59(d), 29.53(d), 29.31(d), 27.18(d), 22.68(d), 16.49(s), 14.12(s). GC / MS (EI): m / z (%): 289 (3) [M+], 272 (5), 247 (5), 176 (5), 163 (25), 147 (7), 91 (100), 65 (8), 55 (5).

[0065] Example 5: (E)-N-Benzyl-2-methylundecane-1-imine oxide Alternatively, N-benzylhydroxylamine hydrochloride for the preparation of the title compound was prepared as follows:

[0066] a) (E)-N-benzyl-1-phenylmethanimine oxide Dibenzylamine (3.51 g, 17.6 mmol) was placed in a 100 mL three-neck round-bottom flask and Na2WO4·2H2O (0.063 g, 0.176 mmol) and methanol (50 ml) were added. The solution was cooled and 30% aqueous hydrogen peroxide (3.99 g, 35.2 mmol) was added dropwise over a period of 3 min under stirring. After stirring at room temperature overnight, the total conversion of dibenzylamine was confirmed by TLC, GC-MS and NMR. The solvent was removed and the residue was purified by column chromatography (heptane:MTBE=4:1-1:1) to give (E)-N-benzyl-1-phenylmethanimine oxide (3.38 g, 15.5 mmol, 88% yield) as a white solid.

[0067] 1 H NMR (400 MHz, CDCl3) δ 8.25 - 8.16 (m, 2H), 7.50 - 7.42 (m, 2H), 7.42 - 7.30 (m, 7H), 5.01 (s, 2H).13 C NMR (101 MHz, CDCl3) δ 134.32(t), 133.35(q), 130.49(t), 129.23(t), 128.98(t), 128.65(t), 128.49(t), 71.25(d). GC / MS (EI): m / z (%): 211 (28) [M + ], 181 (25), 92 (35), 91 (100), 89 (28),77 (12), 65 (72), 63 (18).

[0068] b) N-Benzylhydroxylamine hydrochloride (E)-N-benzyl-1-phenylmethanimine oxide (2.012 g, 9.52 mmol) in DCM (20 ml) was added into the flask, and then 37% aqueous hydrogen chloride solution (1.877 g, 19.05 mmol) was added dropwise at room temperature. The reaction mixture was then stirred at reflux for 2 h. The phases were separated, the aqueous layer was collected, and the organic phase was washed twice with water. The aqueous layers were combined and the water was removed to give N-benzylhydroxylamine hydrochloride (1.25 g, 7.7 mmol, 81% yield) as a white solid, which was used in the next step without further purification.

[0069] 1 H NMR (400 MHz, DMSO) δ 11.87 (s, 2H), 10.99 (s, 1H), 7.60 - 7.48 (m, 2H), 7.46 - 7.30 (m, 3H), 4.30 (s, 2H). 13 C NMR (101 MHz, DMSO) δ 131.29(t), 130.41(q), 129.47(t), 128.88(t), 54.23(d).

[0070] c) (E)-N-benzyl-2-methylundecane-1-imine oxide The final step was carried out as described in Example 4.

[0071] Example 6:(E)-N-Cyclohexyl-2-methylundecane-1-imine oxide The compound was obtained as a white solid (87.0 mmol, 25.00 g, 59% yield) from 2-methylundecanal (164.0 mmol, 30.20 g, 1.1 equiv.) and N-cyclohexylhydroxylamine (149.0 mmol, 16.84 g, 1 equiv.) according to the process of Example 1.

[0072] 1 H NMR (400 MHz, CDCl3) δ 6.51 (d, J = 7.5 Hz, 1H), 3.73 - 3.48 (m, 1H), 3.22 - 2.95 (m, 1H), 2.09 - 1.94 (m, 2H), 1.92 - 1.79 (m, 4H), 1.67 (d, J = 12.3 Hz, 1H), 1.47 - 1.17 (m, 19H), 1.06 (d, J = 6.8 Hz, 3H), 0.88 (t, J = 6.6 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 141.60(t), 73.97(t), 34.25(d), 31.91(d), 31.26(d), 31.11(d), 30.58(t), 29.68(d), 29.58(d), 29.32(d), 27.21(d), 25.09(d), 25.06(d), 25.04(d), 22.69(d), 16.70(s), 14.13(s). GC / MS (EI): m / z (%): 281 (8) [M+], 264 (10), 239 (12), 168 (16), 155 (76), 139 (32), 126 (19), 83 (46), 55 (100).

[0073] Example 7: (Z)-2-Methyl-N-phenylundecane-1-imine oxide The compound was obtained as a white solid (12.1 mmol, 3.50 g, 66% yield) from 2-methylundecanal (20.2 mmol, 3.72 g, 1.1 equiv.) and N-phenylhydroxylamine (18.3 mmol, 4.00 g, 1 equiv.) according to the process of Example 1.

[0074] 1 H NMR (400 MHz, CDCl3) δ 7.77 - 7.57 (m, 2H), 7.53 - 7.32 (m, 3H), 7.05 (d, J = 7.6 Hz, 1H), 3.44 - 3.19 (m, 1H), 1.68 - 1.45 (m, 2H), 1.42 - 1.16 (m, 17H), 0.88 (t, J = 6.5 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 147.93(q), 144.62(t), 129.78(t), 129.01(t), 121.71(t), 34.18(d), 31.89(d), 31.70(t), 29.69(d), 29.57(d), 29.31(d), 27.34(d), 22.68(d), 16.55(s), 14.12(s). GC / MS (EI): m / z (%): 275 (2) [M+], 259 (2), 232 (98), 172 (16), 146 (86),133 (100), 120 (90), 106 (75), 77 (71), 55 (twenty three).

[0075] Example 8: (E)-N-Cyclopentyl-2-methylundecane-1-imine oxide The compound was obtained as a white solid (16.7 mmol, 4.69 g, 77% yield) from 2-methylundecanal (23.9 mmol, 4.40 g, 1.1 equiv.) and N-cyclopentylhydroxylamine (21.7 mmol, 2.15 g, 1 equiv.) according to the process of Example 1.

[0076] 1H NMR (400 MHz, CDCl3) δ 6.58 (d, J = 7.5 Hz, 1H), 4.49 - 4.02 (m, 1H), 3.34 - 2.89 (m, 1H), 2.26 - 2.07 (m, 2H), 2.01 - 1.77 (m, 4H), 1.69 - 1.51 (m, 2H), 1.47 - 1.19 (m, 16H), 1.06 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.7 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 142.42(t), 74.71(t), 34.16(d), 31.90(d), 31.26(d), 31.13(d), 30.81(t), 29.66(d), 29.57(d), 29.56(d), 29.31(d), 27.22(d), 25.52(d), 22.68(d), 16.62(s), 14.12(s). GC / MS (EI): m / z (%): 267 (10) [M+], 250 (12), 225 (15), 200 (7), 154 (32),141 (100), 86 (26), 69 (51), 55 (28).

[0077] Example 9: (E)-N-isopropyl-2-methylundecane-1-imine oxide A mixture of N-isopropylhydroxylamine (30.6 g, 61 mmol, 1 equiv.) (15% w / w aqueous) and methylundecanal (11.26 g, 61 mmol, 1 equiv.) was vigorously stirred for 2 h at rt. Conversion was monitored by TLC. After >95% conversion, the solvent was removed, followed by silica gel chromatography (heptane:MTBE=20:1-0:1) to afford the crude product as a white solid, which was recrystallized from hexane and DCM (10:1) to give (E)-N-isopropyl-2-methylundecane-1-imine oxide (14.254 g, 56.1 mmol, 92% yield) as a white solid.

[0078] 1H NMR (400 MHz, CDCl3) δ 6.52 (d, J = 7.4 Hz, 1H), 4.07 - 3.79 (m, 1H), 3.28 - 2.88 (m, 1H), 1.49 - 1.19 (m, 22H), 1.07 (d, J = 6.5 Hz, 3H), 0.87 (d, J = 5.7 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 141.22(t), 66.15(t), 34.16(d), 31.88(d), 30.58(t), 29.64(d), 29.55(d), 29.29(d), 27.19(d), 22.66(d), 20.89(s), 20.75(s), 16.60(s), 14.09(s). GC / MS (EI): m / z (%): 241 (7) [M+], 226 (7), 199 (11), 184 (11), 128 (36),115 (100), 100 (25), 86(18), 73 (16), 55 (22).

[0079] Example 10: (2E,3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide The compound was obtained as a yellow oil (13.8 mmol, 3.50 g, 26% yield) from β-ionone (57.2 mmol, 6.38 g, 1.1 equiv.) and N-isopropylhydroxylamine hydrochloride (52.0 mmol, 10.0 g, 1 equiv.) according to the process of Example 9.

[0080] 1 H NMR (400 MHz, CDCl3) δ 6.60 - 6.26 (m, 2H), 4.79 - 4.54 (m, 1H), 2.26 (s, 3H), 2.05 (t, J = 6.2 Hz, 2H), 1.74 (s, 3H), 1.68 - 1.57 (m, 2H), 1.53 - 1.46 (m, 2H), 1.39 (d, J = 6.5 Hz, 6H), 1.04 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 143.59(q), 137.54(q), 132.69(t), 131.44(q), 123.82(t), 57.12(t), 39.38(d), 34.20(q), 33.11(d), 28.91(s), 21.76(s), 20.26(s), 19.04(d), 13.92(s). GC / MS (EI): m / z (%): 249 (1) [M+], 234 (3), 216 (1), 207 (2), 192 (100),160 (30), 146 (4), 134 (6), 105 (9).

[0081] Example 11: (E)-2-Methyl-N-(3-methylbut-2-en-1-yl)undecane-1-imine oxide The compound was obtained as a colorless oil (3.0 mmol, 0.85 g, 26% yield) from 2-methylundecanal (12.7 mmol, 2.35 g, 1.1 equiv.) and N-(3-methylbut-2-en-1-yl)hydroxylamine (11.6 mmol, 1.15 g, 1 equiv.) according to the process of Example 1.

[0082] 1 H NMR (400 MHz, CDCl3) δ 6.49 (d, J = 7.5 Hz, 1H), 5.49 - 5.31 (m, 1H), 4.34 (d, J = 7.3 Hz, 2H), 3.21 - 2.95 (m, 1H), 1.82 (s, 3H), 1.72 (s, 3H), 1.34 - 1.20 (m, 15H), 1.07 (d, J = 6.9 Hz, 3H), 0.98 - 0.83 (m, 4H). 13C NMR (101 MHz, CDCl3) δ 143.16(t), 141.04(q), 116.44(t), 62.97(d), 34.20(d), 32.00(d), 31.00(t), 29.75(d), 29.66(d), 29.42(d), 27.29(d), 25.92(s), 22.78(d), 18.21(s), 16.66(s), 14.21(s). GC / MS (EI): m / z (%): 267 (1) [M + ], 252 (1), 196 (1), 180 (1), 156 (4),141 (2), 114 (11), 69 (100), 55 (15).

[0083] Example 12: (Z)-N-(furan-2-ylmethyl)-2-methylundecane-1-imine oxide The compound was obtained as a white solid (8.3 mmol, 2.39 g, 67% yield) from 2-methylundecanal (13.7 mmol, 2.53 g, 1.1 equiv.) and N-(furan-2-ylmethyl)hydroxylamine (12.5 mmol, 1.87 g, 1 equiv.) according to the process of Example 1.

[0084] 1 H NMR (400 MHz, CDCl3) δ 7.49 - 7.40 (m, 1H), 6.51 (d, J = 3.2 Hz, 1H), 6.43 - 6.39 (m, 1H), 6.37 (d, J = 7.6 Hz, 1H), 4.88 (s, 2H), 3.23 - 2.95 (m, 1H), 1.34 - 1.16 (m, 16H), 1.06 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.8 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 146.31(q), 143.97(t), 143.68(t), 112.06(t), 110.98(t), 61.48(d), 34.00(d), 31.89(d), 31.03(t), 29.58(d), 29.52(d), 29.30(d), 27.09(d), 22.67(d), 16.43(s), 14.11(s). GC / MS (EI): m / z (%): 279 (1) [M + ], 261 (1), 236 (1), 204 (1), 180 (6),162 (4), 137 (5), 81 (100), 69 (5).

[0085] Example 13: (E)-N,2-Dimethylundecane-1-imine oxide The compound was obtained as a white solid (39.7 mmol, 7.50 g, 94% yield) from 2-methylundecanal (39.7 mmol, 7.32 g, 1.1 equiv.) and N-methylhydroxylamine hydrochloride (36.1 mmol, 3.01 g, 1 equiv.) according to the process of Example 1.

[0086] 1 H NMR (400 MHz, CDCl3) δ 6.51 (dd, J = 7.6, 0.6 Hz, 1H), 3.82 - 3.45 (m, 3H), 3.22 - 2.84 (m, 1H), 1.49 - 1.18 (m, 16H), 1.08 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.9 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 145.07(t), 52.61(t), 33.95(d), 31.83(d), 31.10(t), 29.59(d), 29.51(d), 29.49(d), 29.25(d), 27.12(d), 22.62(d), 16.35(s), 14.05(s). GC / MS (EI): m / z (%): 213 (4) [M +], 171 (5), 142 (2), 114 (4), 100 (46),87 (100), 70 (45), 60 (36), 55 (70).

[0087] Example 14: (E)-N-Ethyl-2-methylundecane-1-imine oxide The compound was obtained as a white solid (6.9 mmol, 1.60 g, 70% yield) from 2-methylundecanal (10.9 mmol, 1.36 g, 1.1 equiv.) and N-ethylhydroxylamine (9.9 mmol, 0.58 g, 1 equiv.) according to the process of Example 1.

[0088] 1 H NMR (400 MHz, CDCl3) δ 6.52 (d, J = 7.5 Hz, 1H), 3.79 (q, J = 7.2 Hz, 2H), 3.19 - 2.90 (m, 1H), 1.52 - 1.42 (m, 4H), 1.35 - 1.18 (m, 15H), 1.08 (d, J = 6.8 Hz, 3H), 0.88 (t, J = 6.4 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 143.27(t), 60.28(d), 34.10(d), 31.90(d), 30.88(t), 29.67(d), 29.57(d), 29.33(d), 27.19(d), 22.69(d), 16.54(s), 14.14(s), 13.53(s). GC / MS (EI): m / z (%): 227 (1) [M + ], 210 (2), 185 (4), 170 (3), 128 (3),114 (40), 101 (100), 84 (27), 55 (35).

[0089] Example 15: (E)-2-Methyl-N-(2-methylpentyl)undecane-1-imine oxide (mixture of diastereoisomers) The compound was obtained as a colorless oil (24.7 mmol, 7.36 g, 54% yield) from 2-methylundecanal (50.4 mmol, 9.30 g, 1.1 equiv.) and N-(2-methylpentyl)hydroxylamine (45.8 mmol, 5.27 g, 1 equiv.) according to the process of Example 1.

[0090] 1 H NMR (400 MHz, CDCl3) δ 6.47 (d, J = 7.5 Hz, 1H), 3.75 - 3.57 (m, 1H), 3.51 - 3.34 (m, 1H), 3.20 - 2.95 (m, 1H), 2.47 - 2.21 (m, 1H), 1.54 - 1.12 (m, 20H), 1.09 (d, J = 6.9 Hz, 3H), 0.95 - 0.82 (m, 9H). 13 C NMR (101 MHz, CDCl3) δ 144.45(t), 71.68(d), 71.65(d), 36.10(d), 34.07(d), 33.99(d), 31.80(d), 30.83(t), 30.40(t), 30.39(t), 29.57(d), 29.54(d), 29.47(d), 29.22(d), 27.22(d), 22.58(d), 19.69(d), 19.67(d), 16.84(s), 16.75(s), 16.52(s), 14.08(s), 14.07(s), 14.00(s). GC / MS (EI): m / z (%): 283 (2) [M + ], 266 (5), 241 (5), 212 (10), 170 (20),157 (20), 128 (100), 112 (11), 86 (21).

[0091] Example 16: (E)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylundecane-1-imine oxide The compound was obtained from 2-methylundecanal (16.9 mmol, 3.11 g, 1.1 equiv.) and N-(benzo[d][1,3]dioxol-5-ylmethyl)-hydroxylamine (15.3 mmol, 2.53 g, 1 equiv.) according to the process of Example 1 as a white solid (12.6 mmol, 4.20 g, 82% yield).

[0092] 1 H NMR (400 MHz, CDCl3) δ 6.89 (s, 1H), 6.83 (dd, J = 16.9, 7.8 Hz, 2H), 6.45 (d, J = 7.4 Hz, 1H), 5.98 (s, 2H), 4.75 (s, 2H), 3.17 - 2.91 (m, 1H), 1.45 - 1.18 (m, 16H), 1.05 (d, J = 6.4 Hz, 3H), 0.87 (d, J = 6.7 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 148.16(q), 148.06(q), 143.93(t), 126.77(q), 123.22(t), 109.58(t), 108.50(t), 101.33(d), 69.15(d), GC / MS (EI): m / z (%): 333 (1) [M + ], 315 (13), 272 (4), 258 (11), 216 (28), 202 (100), 172 (14), 148 (86), 135 (60).

[0093] Example 17: 2-Methyl-N-(naphthalene-2-ylmethyl)undecane-1-imine oxide The compound was obtained as a white solid (15.0 mmol, 5.20 g, 87% yield) from 2-methylundecanal (18.98 mmol, 3.50 g, 1.1 equiv.) and N-(naphthalen-2-ylmethyl)hydroxylamine (17.25 mmol, 2.95 g, 1 equiv.) according to the process of Example 1.

[0094] 1 H NMR (400 MHz, CDCl3) δ 7.86 (s, 4H), 7.56 - 7.37 (m, 3H), 6.50 (d, J = 7.3 Hz, 1H), 5.03 (s, 2H), 3.24 - 2.95 (m, 1H), 1.51 - 1.14 (m, 16H), 1.06 (d, J = 6.4 Hz, 3H), 0.87 (d, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 144.37(t), 133.33(q), 133.28(q), 130.60(q), 128.82(t), 128.78(t), 128.09(t), 127.75(t), 126.63(t), 126.51(t), 126.21(t), 69.61(d), 34.05(d), 31.89(d), 31.07(t), 29.61(d), 29.54(d), 29.32(d), 27.22(d), 22.70(d), 16.54(s), 14.13(s). GC / MS (EI): m / z (%): 339 (1) [M + ], 321 (18), 264 (19), 222 (30), 208 (94), 154 (81), 141 (100), 127 (24), 81 (18).

[0095] Example 18: (Z)-2-Methyl-N-(2-methylundecyl)undecane-1-imine oxide (mixture of diastereoisomers) The compound was obtained as a white solid (10.9 mmol, 4.01 g, 74% yield) from 2-methylundecanal (16.3 mmol, 3.00 g, 1.1 equiv.) and N-(2-methylundecyl)hydroxylamine (14.8 mmol, 2.95 g, 1 equiv.) according to the process of Example 1.

[0096] 1 H NMR (400 MHz, CDCl3) δ 6.45 (d, J = 7.5 Hz, 1H), 3.80 - 3.55 (m, 1H), 3.49 - 3.36 (m, 1H), 3.23 - 2.97 (m, 1H), 2.42 - 2.19 (m, 1H), 1.37 - 1.19 (m, 32H), 1.08 (d, J = 6.8 Hz, 3H), 0.96 - 0.75 (m, 10H). 13 C NMR (101 MHz, CDCl3) δ 144.83(t), 71.80(d), 71.78(d), 34.17(d), 34.09(d), 33.97(d), 31.90(d), 30.95(t), 30.71(t), 29.82(d), 29.77(d), 29.69(d), 29.64(d), 29.59(d), 29.33(d), 27.32(d), 27.29(d), 26.61(d), 22.68(d), 17.00(s), 16.91(s), 16.62(s), 14.11(s). GC / MS (EI): m / z (%): 367 (1) [M + ], 334 (1), 294 (1), 264 (3), 250 (6), 225 (6), 196 (100), 180 (18), 154 (8).

[0097] Example 19: (E)-N-(4-Methoxybenzyl)-2-methylundecane-1-imine oxide The compound was obtained as a white solid (8.2 mmol, 2.62 g, 71% yield) from 2-methylundecanal (12.7 mmol, 2.34 g, 1.1 equiv.) and N-(4-methoxybenzyl)hydroxylamine (11.5 mmol, 1.74 g, 1 equiv.) according to the process of Example 1.

[0098] 1 H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 8.5 Hz, 2H), 6.41 (d, J = 7.5 Hz, 1H), 4.79 (s, 2H), 3.82 (s, 3H), 3.15 - 2.95 (m, 1H), 1.42 - 1.18 (m, 16H), 1.04 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 160.03(q), 143.86(t), 130.77(t), 125.17(q), 114.31(t), 68.80(d), 55.32(s), 34.03(d), 31.90(d), GC / MS (EI): m / z (%): 319 (1) [M+], 274 (1), 255 (3), 176 (2), 146 (5), 121 (100), 108 (4), 91 (14), 77 (35).

[0099] Example 20: (E)-3-(4-isobutyl-2-methylphenyl)-N-methylpropan-1-imine oxide The compound was obtained as a pale yellow oil (13.2 mmol, 3.27 g, 91% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (16.0 mmol, 3.27 g, 1.1 equiv.) and methylhydroxylamine hydrochloride (14.6 mmol, 1.22 g, 1 equiv.) according to the process of Example 1.

[0100] 1 H NMR (400 MHz, CDCl3) δ 7.05 (d, J = 5.9 Hz, 1H), 6.95 - 6.89 (m, 2H), 6.69 (t, J = 5.2 Hz, 1H), 3.66 (s, 3H), 2.85 - 2.64 (m, 4H), 2.40 (d, J = 7.1 Hz, 2H), 2.30 (s, 4H), 0.89 (d, J = 6.7 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.84(q), 139.56(t), 135.67(q), 135.66(q), 131.23(t), 128.91(t), 128.14(t), 126.84(t), 52.41(s), 44.98(d), 30.19(t), 28.15(d), 26.98(d), 22.44(s), 19.30(s). GC / MS (EI): m / z (%): 233 (6) [M + ], 216 (29), 187 (40), 161 (100), 143 (27), 128 (31), 119 (71), 105 (30), 91 (38).

[0101] Example 21: (E)-N-Benzyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained as a white solid (10.6 mmol, 3.49 g, 82% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (14.2 mmol, 2.90 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (12.9 mmol, 2.06 g, 1 equiv.) according to the process of Example 1.

[0102] 1H NMR (400 MHz, CDCl3) δ 7.43 - 7.28 (m, 5H), 6.96 - 6.85 (m, 3H), 6.64 (t, 1H), 4.85 (s, 2H), 2.82 - 2.71 (m, 4H), 2.40 (d, J = 7.1 Hz, 2H), 2.25 (s, 3H), 1.90 - 1.77 (m, 1H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.79(q), 138.59(t), 135.71(q), 135.66(q), 132.82(q), 131.19(t), 129.43(t), 128.94(t), 128.30(t), 126.80(t), 69.27(d), 45.00(d), 30.23(t), 28.19(d), 26.92(d), 22.47(s), 19.31(s).GC / MS (EI): m / z (%): 309 (3) + ], 292 (8), 250 (1), 187 (14), 161 (42), 143 (6), 131 (10), 119 (19), 91 (100).

[0103] Example 22: (E)-N-Ethyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained as a pale yellow oil (12.3 mmol, 3.26 g, 58% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (23.3 mmol, 4.76 g, 1.1 equiv.) and ethylhydroxylamine (21.2 mmol, 1.25 g, 1 equiv.) according to the process of Example 1.

[0104] 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J = 7.6 Hz, 1H), 6.96 - 6.90 (m, 2H), 6.73 (t, J = 5.3 Hz, 1H), 3.79 (q, J = 7.3 Hz, 2H), 2.87 - 2.71 (m, 5H), 2.50 - 2.35 (m, 3H), 2.33 - 2.24 (m, 4H), 1.87 - 1.79 (m, 1H), 1.45 (t, J = 7.3 Hz, 3H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.80(q), 137.98(t), 135.70(q), 135.66(q), 131.20(t), 128.19(t), 126.80(t), 60.04(d), 44.97(d), 30.18(t), 28.22(d), 26.78(d), 22.43(s), 19.31(s), 13.32(s). GC / MS (EI): m / z (%): 247 (7) [M + ], 230 (15), 187 (34), 161 (100), 143 (10), 131 (17), 119 (50), 105 (18), 91 (18).

[0105] Example 23: (E)-3-(4-isobutyl-2-methylphenyl)-N-(4-methoxybenzyl)propan-1-imine oxide The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (33.9 mmol, 7.28 g, 1.1 equiv.) and N-(4-methoxybenzyl)hydroxylamine (30.8 mmol, 4.65 g, 1 equiv.) according to the process of Example 1 as a white solid (21.65 mmol, 7.5 g, 70% yield).

[0106] 1H NMR (400 MHz, CDCl3) δ 7.37 - 7.18 (m, 2H), 6.98 - 6.79 (m, 5H), 6.59 (t, J = 5.3 Hz, 1H), 4.80 (s, 2H), 3.82 (s, 3H), 2.85 - 2.63 (m, 4H), 2.40 (d, J = 7.1 Hz, 2H), 2.25 (s, 3H), 1.84 - 1.79 (m, 1H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 160.11(q), 139.77(q), 138.16(t), 135.75(q), 135.65(q), 131.17(t), 131.06(t), 128.30(t), 126.76(t), GC / MS (EI): m / z (%): 339 (1) [M + ], 323 (2), 280 (1), 202 (9), 185 (3), 162 (6), 121 (100), 91 (8), 78 (7).

[0107] Example 24: (E)-3-(4-isobutyl-2-methylphenyl)-N-isopropylpropan-1-imine oxide The compound was obtained as a white solid (9.6 mmol, 2.66 g, 51% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (18.7 mmol, 4.03 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 18.7 mmol, 9.37 g, 1 equiv.) according to the process of Example 9.

[0108] 1H NMR (300 MHz, CDCl3) δ 7.10 - 6.99 (m, 1H), 6.97 - 6.84 (m, 2H), 6.73 (t, J = 5.3 Hz, 1H), 4.12 - 3.92 (m, 1H), 2.93 - 2.64 (m, 4H), 2.40 (d, J = 7.1 Hz, 2H), 2.31 (s, 3H), 1.90 - 1.74 (m, 1H), 1.40 (d, J = 6.5 Hz, 6H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (75 MHz, CDCl3) δ 139.86(q), 135.96(q), 135.81(q), 135.70(t), 131.27(t), 128.34(t), 126.86(t), 66.20(t), 45.08(d), 30.29(t), 28.44(d), 26.65(d), 22.54(s), 20.87(s), 19.45(s). GC / MS (EI): m / z (%): 261 (10) [M + ], 244 (10), 230 (5), 202 (4), 187 (36), 161 (100), 131 (17), 119 (48), 105 (19).

[0109] Example 25: (E)-N-Cyclohexyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained as a white solid (11.3 mmol, 3.59 g, 77% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (16.2 mmol, 3.31 g, 1.1 equiv.) and N-cyclohexylhydroxylamine (14.7 mmol, 1.66 g, 1 equiv.) according to the process of Example 1.

[0110] 1H NMR (400 MHz, CDCl3) δ 7.07 - 6.99 (m, 1H), 6.98 - 6.83 (m, 2H), 6.72 (t, J = 5.4 Hz, 1H), 3.75 - 3.50 (m, 1H), 2.86 - 2.69 (m, 4H), 2.40 (d, J = 7.2 Hz, 2H), 2.30 (s, 3H), 2.01 - 1.92 (m, 2H), 1.90 - 1.74 (m, 5H), 1.66 (d, J = 12.2 Hz, 1H), 1.36 - 1.07 (m, 3H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.72(q), 136.13(t), 135.86(q), 135.69(q), 131.16(t), 128.23(t), 126.76(t), 73.81(t), 44.98(d), GC / MS (EI): m / z (%): 301 (6) [M + ], 284 (13), 242 (6), 207 (14), 187 (27), 161 (100), 131 (21), 119 (40), 83 (20).

[0111] Example 26: (E)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (32.1 mmol, 6.91 g, 1.1 equiv.) and N-(benzo[d][1,3]dioxol-5-ylmethyl)hydroxylamine (29.2 mmol, 4.82 g, 1 equiv.) according to the process of Example 1 as a white solid (19.8 mmol, 7.01 g, 68% yield).

[0112] 1H NMR (400 MHz, CDCl3) δ 6.99 - 6.93 (m, 1H), 6.93 - 6.77 (m, 5H), 6.63 (t, J = 5.1 Hz, 1H), 5.98 (s, 2H), 4.75 (s, 2H), 2.86 - 2.69 (m, 4H), 2.40 (d, J = 7.2 Hz, 2H), 2.31 - 2.23 (m, 3H), 1.85 - 1.79 (m, 1H), 0.89 (d, J = 6.5 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 148.25(q), 148.07(q), 139.83(q), 138.28(t), 135.71(q), 135.66(q), 131.19(t), 128.29(t), 126.78(t), 126.33(q), 123.55(t), 109.85(t), 108.52(t), 101.38(d), 68.99(d), 44.98(d), 30.22(t), 28.21(d), 26.89(d), 22.46(s), 19.32(s). GC / MS (EI): m / z (%): 353 (1) [M + ], 294 (1), 220 (17), 185 (5), 176 (12), 135 (100), 129 (6), 105 (9), 71 (18).

[0113] Example 27: (E)-3-(4-isobutyl-2-methylphenyl)-N-(1-(naphthalen-2-yl)ethyl)propan-1-imine oxide The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (33.7 mmol, 7.24 g, 1.1 equiv.) and N-(1-(naphthalen-2-yl)ethyl)hydroxylamine (30.6 mmol, 5.66 g, 1 equiv.) according to the process of Example 1 as a white solid (18.4 mmol, 7.01 g, 60% yield).

[0114] 1H NMR (400 MHz, CDCl3) δ 7.98 - 7.67 (m, 4H), 7.62 - 7.42 (m, 3H), 6.98 - 6.85 (m, 2H), 6.83 - 6.70 (m, 2H), 5.13 (q, J = 6.7 Hz, 1H), 2.76 (s, 4H), 2.37 (d, J = 7.1 Hz, 2H), 2.23 (s, 3H), 1.93 - 1.69 (m, 4H), 0.88 (d, J = 6.5 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.73(q), 137.15(t), 135.77(q), 135.73(q), 135.65(q), 133.34(q), 133.16(q), 131.14(t), 128.59(t), 128.28(t), 128.22(t), 127.67(t), 126.73(t), 126.65(t), 126.51(t), 126.40(t), 125.03(t), 73.63(t), 44.98(d), 30.20(t), 28.24(d), 26.77(d), 22.47(s), 19.33(s), 19.12(s). GC / MS (EI): m / z (%): 373 (1) [M + ], 357 (3), 342 (3), 202 (17), 196 (7), 155 (100), 143 (5), 129 (10), 115 (9).

[0115] Example 28: (E)-3-(4-isobutyl-2-methylphenyl)-N-(2-methylundecyl)propan-1-imine oxide The compound was obtained as a white solid (15.5 mmol, 6.01 g, 60% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (28.6 mmol, 6.15 g, 1.1 equiv.) and N-(2-methylundecyl)hydroxylamine (26.0 mmol, 5.18 g, 1 equiv.) according to the process of Example 1.

[0116] 1H NMR (400 MHz, CDCl3) δ 7.07 - 7.00 (m, 1H), 6.96 - 6.86 (m, 2H), 6.64 (t, J = 5.4 Hz, 1H), 3.66 (dd, J = 11.8, 6.3 Hz, 1H), 3.43 (dd, J = 11.8, 8.3 Hz, 1H), 2.93 - 2.70 (m, 4H), 2.40 (d, J = 7.2 Hz, 2H), 2.31 (s, 4H), 1.89 - 1.77 (m, 1H), 1.37 - 1.21 (m, 16H), 0.92 - 0.84 (m, 12H). 13 C NMR (101 MHz, CDCl3) δ 139.79(q), 138.77(t), 135.75(q), 135.71(q), 131.20(t), 128.13(t), 126.79(t), 71.74(d), 44.99(d), 34.06(d), 31.91(d), 30.79(t), 30.20(t), 29.78(d), 29.62(d), 29.59(d), 29.34(d), 28.28(d), 26.65(d), 22.69(d), 22.43(s), 19.34(s), 17.04(s), 14.13(s). GC / MS (EI): m / z (%): 387 (1) [M + ], 372 (1), 315 (1), 242 (3), 229 (4), 215 (7), 161 (100), 119 (49), 105 (22).

[0117] Example 29: (E)-N-(sec-butyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained as a pale yellow oil (11.9 mmol, 3.49 g, 51% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (25.5 mmol, 5.21 g, 1.1 equiv.) and N-(sec-butyl)hydroxylamine (23.2 mmol, 2.00 g, 1 equiv.) according to the process of Example 1.

[0118] 1 H NMR (400 MHz, CDCl3) δ 7.04 (d, J = 7.5 Hz, 1H), 6.97 - 6.87 (m, 2H), 6.70 (t, J = 5.3 Hz, 1H), 3.76 - 3.58 (m, 1H), 2.92 - 2.67 (m, 4H), 2.53 - 2.37 (m, 2H), 2.34 - 2.28 (m, 3H), 2.03 - 1.89 (m, 1H), 1.88 - 1.77 (m, 1H), 1.62 - 1.47 (m, 1H), 1.37 (t, J = 10.4 Hz, 3H), 0.95 - 0.81 (m, 9H). 13 C NMR (101 MHz, CDCl3) δ 139.71(q), 136.70(t), 135.86(q), 135.68(q), 131.16(t), 128.21(t), 126.76(t), 72.40(t), 44.98(d), 30.18(t), 28.39(d), 27.04(d), 26.46(d), 22.42(s), 19.34(s), 19.06(s), 10.63(s).GC / MS (EI): m / z (%): 275 (3) + ], 246 (12), 187 (40), 161 (100), 131 (18), 119 (52), 105 (25), 57 (36).

[0119] Example 30: (E)-3-(4-isobutyl-2-methylphenyl)-N-(1-phenylethyl)propan-1-imine oxide The compound was obtained as a pale yellow oil (15.4 mmol, 5.26 g, 60% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (28.3 mmol, 5.78 g, 1.1 equiv.) and N-(1-phenylethyl)hydroxylamine (25.7 mmol, 3.47 g, 1 equiv.) according to the process of Example 1.

[0120] 1H NMR (400 MHz, CDCl3) δ 7.44 - 7.28 (m, 5H), 6.94 - 6.80 (m, 3H), 6.72 (t, J = 5.5 Hz, 1H), 5.03 - 4.82 (m, 1H), 2.86 - 2.64 (m, 4H), 2.40 (d, 2H), 2.31 - 2.20 (m, 3H), 1.89 - 1.71 (m, 4H), 0.89 (d, J = 6.7 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.71(q), 138.36(q), 137.02(t), 135.84(q), 135.66(q), 131.17(t), 128.73(t), 128.65(t), 128.62(t), 128.34(t), 127.40(t), 126.80(t), 73.46(t), 45.04(d), 30.24(t), 28.25(d), 26.80(d), 22.50(s), 19.35(s), 19.07(s). GC / MS (EI): m / z (%): 323 (43) [M + ], 218 (19), 176 (24), 162 (29), 131 (29), 119 (33), 105 (100), 91 (31), 77 (29).

[0121] Example 31: (Z)-N-Cyclobutyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide The compound was obtained as a white solid (12.8 mmol, 3.69 g, 46% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (31.0 mmol, 6.34 g, 1.1 equiv.) and N-cyclobutylhydroxylamine (28.2 mmol, 2.40 g, 1 equiv.) according to the process of Example 1.

[0122] 1H NMR (400 MHz, CDCl3) δ 7.10 - 6.99 (m, 1H), 6.98 - 6.83 (m, 2H), 6.72 (t, J = 5.1 Hz, 1H), 3.63 (t, J = 11.3 Hz, 1H), 2.84 - 2.75 (m, 3H), 2.40 (d, J = 7.1 Hz, 2H), 2.30 (s, 3H), 2.05 - 1.73 (m, 7H), 1.66 (d, J = 12.4 Hz, 1H), 0.89 (d, J = 6.7 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.75(q), 136.19(t), 135.86(q), 135.72(q), 131.17(t), 128.22(t), 126.77(t), 73.82(t), 44.98(d), GC / MS (EI): m / z (%): 273 (1) [M + ], 268 (3), 187 (31), 161 (55), 131 (32), 119 (100), 105 (25), 83 (9), 55 (55).

[0123] Example 32: (E)-3-(4-isobutyl-2-methylphenyl)-N-(3-methylbut-2-en-1-yl)propan-1-imine oxide The compound was obtained as a pale yellow oil (4.5 mmol, 1.37 g, 26% yield) from 3-(4-isobutyl-2-methylphenyl)propanal (19.5 mmol, 3.99 g, 1.1 equiv.) and N-(3-methylbut-2-en-1-yl)hydroxylamine (17.8 mmol, 2.44 g, 1 equiv.) according to the process of Example 1.

[0124] 1H NMR (400 MHz, CDCl3) δ 7.01 (d, J = 7.5 Hz, 1H), 6.96 - 6.83 (m, 2H), 6.71 (t, J = 5.3 Hz, 1H), 5.40 (t, J = 7.2 Hz, 1H), 4.34 (d, J = 7.4 Hz, 2H), 2.89 - 2.66 (m, 4H), 2.40 (d, J = 7.1 Hz, 2H), 2.30 (s, 3H), 1.89 - 1.76 (m, 4H), 1.68 (s, 3H), 0.89 (d, J = 6.6 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 141.34(q), 139.79(q), 137.49(t), 135.84(q), 135.68(q), 131.19(t), 128.31(t), 126.77(t), 116.02(t), GC / MS (EI): m / z (%): 287 (2) [M + ], 219 (2), 207 (4), 187 (3), 161 (15), 131 (7), 119 (17), 105 (10), 69 (100).

[0125] Example 33: (E)-N-isopropyl dodecane-1-imine oxide The compound was obtained as a pale yellow oil (14.5 mmol, 3.50 g, 53% yield) from dodecanal (27.1 mmol, 5.01 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 27.1 mmol, 13.58 g, 1 equiv.) according to the process of Example 9.

[0126] 1H NMR (300 MHz, CDCl3) δ 6.71 (t, J = 5.7 Hz, 1H), 4.13 - 3.89 (m, 1H), 2.59 - 2.35 (m, 2H), 1.58 - 1.45 (m, 2H), 1.42 (d, J = 6.5 Hz, 6H), 1.35 - 1.16 (m, 16H), 0.88 (t, J = 5.7 Hz, 3H). 13 C NMR (75 MHz, CDCl3) δ 136.57(t), 65.97(t), 31.89(d), 29.58(d), 29.48(d), 29.30(d), 26.46(d), 25.68(d), 22.66(d), 20.78(s), 14.09(s). GC / MS (EI): m / z (%): 241 (2) [M + ], 226 (3), 198 (1), 128 (4), 114 (31),101 (100), 86 (40), 72 (25), 55 (30).

[0127] Example 34: (Z)-7-Hydroxy-N-isopropyl-3,7-dimethyloctan-1-imine oxide The compound was obtained as a pale yellow oil (13.2 mmol, 3.13 g, 73% yield) from 7-hydroxy-3,7-dimethyloctanal (18.1 mmol, 3.13 g, 1 equiv.) and N-isopropylhydroxylamine (15% solution in water, 18.1 mmol, 9.08 g, 1 equiv.) according to the process of Example 9.

[0128] 1 H NMR (300 MHz, CDCl3) δ 6.76 (t, J = 5.8 Hz, 1H), 4.22 - 3.69 (m, 1H), 2.64 - 2.43 (m, 1H), 2.41 - 2.22 (m, 1H), 1.97 - 1.67 (m, 2H), 1.52 - 1.12 (m, 18H), 0.95 (d, J = 6.7 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 135.78(t), 70.71(q), 66.12(t), 43.96(d), 37.46(d), 33.47(d), 30.79(t), 29.29(s), 29.17(s), 21.70(d), 20.82(s), 20.03(s). GC / MS (EI): m / z (%): 229 (1) [M + ], 214 (21), 196 (27), 156 (15), 128 (60),112 (21), 101 (100), 86 (74), 59 (88).

[0129] Example 35: (E)-3-(4-isobutylphenyl)-N-isopropyl-2-methylpropan-1-imine oxide The compound was obtained as a white solid (10.4 mmol, 2.72 g, 21% yield) from 3-(4-isobutylphenyl)-2-methylpropanal (48.9 mmol, 10.00 g, 1 equiv.) and N-isopropylhydroxylamine (15% aqueous solution, 48.9 mmol, 24.53 g, 1 equiv.) according to the process of Example 9.

[0130] 1 H NMR (300 MHz, CDCl3) δ 7.17 - 6.89 (m, 4H), 6.53 (d, J = 7.2 Hz, 1H), 4.03 - 3.80 (m, 1H), 3.50 - 3.17 (m, 1H), 2.92 - 2.76 (m, 1H), 2.75 - 2.60 (m, 1H), 2.43 (d, J = 7.1 Hz, 2H), 1.90 - 1.71 (m, 1H), 1.44 - 1.27 (m, 6H), 1.08 (d, J = 6.9 Hz, 3H), 0.88 (d, J = 6.6 Hz, 6H). 13C NMR (75 MHz, CDCl3) δ 140.25(t), 139.53(q), 136.37(q), 129.00(t), 128.80(t), 66.17(t), 45.04(d), 38.88(d), 32.08(t), 30.21(t), 22.36(s), 20.81(s), 20.67(s), 16.27(s). GC / MS (EI): m / z (%): 261 (1) [M + ], 246 (2), 187 (35), 147 (100), 131 (12),105 (74), 91 (50), 72 (29), 57 (14).

[0131] Example 36: (E)-N-isopropyl-2,6-dimethylhept-5-en-1-imine oxide The compound was obtained as a pale yellow oil (12.4 mmol, 2.57 g, 80% yield) from 2,6-dimethylhept-5-enal (15.4 mmol, 2.16 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 15.4 mmol, 7.70 g, 1 equiv.) according to the process of Example 9.

[0132] 1 H NMR (300 MHz, CDCl3) δ 6.42 (d, J = 7.4 Hz, 1H), 4.94 (t, J = 7.1 Hz, 1H), 3.96 - 3.66 (m, 1H), 3.06 - 2.86 (m, 1H), 1.95 - 1.62 (m, 2H), 1.51 (s, 3H), 1.46 - 1.40 (m, 3H), 1.37 - 1.17 (m, 8H), 0.92 (d, J = 6.9 Hz, 3H). 13 C NMR (75 MHz, CDCl3) δ 140.81(t), 131.54(q), 123.75(t), 65.91(t), 33.95(d), 30.21(t), 25.53(d), 25.50(t), 20.67(s), 20.53(s), 17.41(s), 16.28(s). GC / MS (EI): m / z (%): 197 (24) [M+ ], 182 (100), 140 (27), 123 (30), 115 (10),100 (9), 96 (9), 81 (24), 55 (15).

[0133] Example 37: (E)-N-isopropyl-2-methyldecane-1-imine oxide The compound was obtained as a pale yellow oil (41.6 mmol, 9.75 g, 70% yield) from 2-methyldecanal (59.5 mmol, 10.12 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 59.5 mmol, 29.80 g, 1 equiv.) according to the process of Example 9.

[0134] 1 H NMR (300 MHz, CDCl3) δ 6.53 (d, J = 7.5 Hz, 1H), 4.08 - 3.89 (m, 1H), 3.24 - 2.96 (m, 1H), 1.50 - 1.35 (m, 8H), 1.34 - 1.18 (m, 12H), 1.08 (t, J = 6.6 Hz, 3H), 0.87 (t, J = 6.5 Hz, 3H). 13 C NMR (75 MHz, CDCl3) δ 141.19(t), 66.11(t), 34.13(d), 31.82(d), 30.55(t), 29.61(d), 29.48(d), 29.21(d), 27.16(d), 22.61(d), 20.86(s), 20.71(s), 16.57(s), 14.05(s). GC / MS (EI): m / z (%): 227 (7) [M + ], 212 (7), 185 (12), 170 (12), 142 (4),128 (37), 115 (100), 100 (31), 86 (23).

[0135] Example 38: (Z)-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-isopropylmethanimine oxide (mixture of diastereoisomers) The compound was obtained as a colorless oil (9.2 mmol, 2.58 g, 55% yield) from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (16.8 mmol, 3.53 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 16.8 mmol, 8.40 g, 1 equiv.) according to the process of Example 9.

[0136] 1 H NMR (300 MHz, CDCl3) δ 6.63 (d, J = 7.1 Hz, 1H), 5.49 - 5.32 (m, 1H), 4.17 - 3.90 (m, 1H), 3.33 - 3.02 (m, 1H), 2.41 - 2.17 (m, 1H), 2.13 - 1.80 (m, 7H), 1.67 - 1.35 (m, 11H), 1.23 (s, 6H). 13 C NMR (75 MHz, CDCl3) δ 139.85(t), 137.74(q), 135.86(q), 120.74(t), 118.93(t), 70.61(q), 66.11(t), 43.49(d), 43.44(d), 38.12(d), 38.02(d), 31.20(t), 30.83(t), 30.56(d), 29.27(t), 29.19(t), 29.14(t), 27.89(d), 26.87(d), 24.75(d), 24.43(d), 23.82(d), 22.34(d), 22.27(d), 20.86(s), 20.74(s). GC / MS (EI): m / z (%): 267 (29) [M + ], 252 (30), 232 (21), 180 (33), 150 (29), 117 (76), 105 (50), 91 (79), 59 (100).

[0137] Example 39: (Z)-4-(4-hydroxyphenyl)-N-isopropylbutan-2-imine oxide (mixture of isomers) The compound was obtained as a colorless oil (15.0 mmol, 3.52 g, 23% yield) from 4-(4-hydroxyphenyl)butan-2-one (64.3 mmol, 10.56 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 64.3 mmol, 32.20 g, 1 equiv.) according to the process of Example 9.

[0138] 1 H NMR (300 MHz, CDCl3) δ 9.70 (s, 1H), 7.07 - 6.89 (m, 2H), 6.87 - 6.73 (m, 2H), 4.52 - 3.57 (m, 1H), 2.93 - 2.59 (m, 4H), 2.19 - 1.91 (m, 3H), 1.43 - 1.14 (m, 6H). 13 C NMR (75 MHz, CDCl3) δ 156.56(q), 155.87(q), 149.71(q), 149.26(q), 130.69(q), 129.24(t), 129.16(t), 116.05(t), 115.66(t), 57.59(t), 57.23(t), 36.09(d), 35.46(d), 32.29(d), 29.62(d), 19.79(s), 19.62(s), 19.10(s), 18.91(s). GC / MS (EI): m / z (%): 221 (1) [M + ], 164 (42), 149 (8), 131 (4), 121 (14),107 (100), 94 (14), 77 (24), 65 (7).

[0139] Example 40: (E)-N-isopropyldec-9-en-1-imine oxide The compound was obtained as a pale yellow oil (37.9 mmol, 8.00 g, 39% yield) from dec-9-enal (97.0 mmol, 15.01 g, 1 equiv.) and N-isopropylhydroxylamine (15% solution in water, 97.0 mmol, 48.70 g, 1 equiv.) according to the process of Example 9.

[0140] 1H NMR (300 MHz, CDCl3) δ 6.73 (t, J = 5.7 Hz, 1H), 5.94 - 5.32 (m, 1H), 4.98 - 4.83 (m, 1H), 4.14 - 3.88 (m, 1H), 2.48 (dd, J = 13.4, 7.4 Hz, 2H), 2.03 (dd, J = 13.1, 6.3 Hz, 2H), 1.65 - 1.09 (m, 17H). 13 C NMR (75 MHz, CDCl3) δ 138.96(t), 136.48(t), 114.11(d), 65.87(t), 33.66(d), 29.34(d), 29.05(d), 28.86(d), 28.75(d), 26.37(d), 25.56(d), 20.70(s). GC / MS (EI): m / z (%): 211 (2`) [M + ], 196 (6), 154 (3), 114 (31), 101 (100), 86 (43), 72 (28), 69 (14), 59 (24).

[0141] Example 41: (E)-N-isopropyl-3-(3-isopropylphenyl)butan-1-imine oxide The compound was obtained as a pale yellow oil (20.2 mmol, 5.01 g, 39% yield) from 3-(3-isopropylphenyl)butanal (52.6 mmol, 10.02 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 52.6 mmol, 26.30 g, 1 equiv.) according to the process of Example 9.

[0142] 1 H NMR (300 MHz, CDCl3) δ 7.33 - 7.16 (m, 1H), 7.12 - 6.95 (m, 3H), 6.56 (t, J = 3.2 Hz, 1H), 4.07 - 3.78 (m, 1H), 3.18 - 2.96 (m, 1H), 2.95 - 2.60 (m, 3H), 1.41 - 1.03 (m, 15H). 13C NMR (75 MHz, CDCl3) δ 149.15(q), 145.66(q), 135.15(t), 128.49(t), 125.10(t), 124.43(t), 124.11(t), 66.02(t), 36.83(t), 34.45(d), 34.13(t), 24.04(s), 22.59(s), 20.75(s), 20.69(s). GC / MS (EI): m / z (%): 247 (2) [M + ], 230 (2), 216 (2), 173 (67), 147 (100),131 (28), 105 (61), 91 (50), 86 (19).

[0143] Example 42: (E)-N-isopropyl-1-(naphthalene-2-yl)ethane-1-imine oxide The compound was obtained from 1-(naphthalen-2-yl)ethan-1-one (58.8 mmol, 10.0 g, 1.1 equiv.) and N-isopropylhydroxylamine hydrochloride (53.4 mmol, 5.96 g, 1 equiv.) according to the process of Example 9 as a yellow oil (11.0 mmol, 2.50 g, 21% yield).

[0144] 1 H NMR (300 MHz, CDCl3) δ 8.02 - 7.79 (m, 3H), 7.75 - 7.64 (m, 1H), 7.62 - 7.49 (m, 2H), 7.42 - 7.17 (m, 1H), 4.67 - 4.37 (m, 1H), 2.50 (s, 3H), 1.37 (d, J = 6.4 Hz, 6H). 13 C NMR (75 MHz, CDCl3) δ 145.33(q), 133.92(q), 133.01(q), 132.99(q), 129.05(t), 128.17(t), 127.83(t), 127.18(t), 127.06(t), 126.54(t), 124.46(t), 59.15(t), 20.80(s), 20.38(s). GC / MS (EI): m / z (%): 227 (1) [M+ ], 185 (55), 168 (30), 153 (27), 144 (40), 127 (100), 115 (50), 77 (22), 63 (30).

[0145] Example 43: (E)-N-isopropyl-3-(2-methoxy-2-oxoethyl)-2-pentylcyclopentan-1-imine oxide (mixture of isomers) The compound was obtained as a yellow oil (17.4 mmol, 5.20 g, 16% yield) from methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (110.0 mmol, 25.00 g, 1 equiv.) and N-isopropylhydroxylamine (15% in water, 110.0 mmol, 55.30 g, 1 equiv.) according to the process of Example 9.

[0146] 1 H NMR (300 MHz, CDCl3) δ 4.33 - 4.07 (m, 1H), 3.74 - 3.56 (m, 3H), 2.89 - 2.32 (m, 5H), 2.30 - 2.06 (m, 2H), 1.65 - 1.22 (m, 15H), 0.98 - 0.78 (m, 3H). 13 C NMR (75 MHz, CDCl3) δ 172.60(q), 172.47(q), 156.31(q), 154.14(q), 59.87(t), 59.28(t), 51.53(s), 51.46(s), 47.99(t), 47.66(t), 39.89(t), 38.74(d), 38.63(d), 38.50(t), 32.04(d), 31.69(d), 31.56(d), 28.88(d), 28.62(d), 28.10(d), 28.05(d), 27.04(d), 26.83(d), 26.40(d), 22.52(d), 22.41(d), 20.14(s), 19.88(s), 19.79(s), 19.18(s), 13.97(s), 13.89(s). GC / MS (EI): m / z (%): 283 (6) [M +], 252 (6), 212 (23), 181 (24), 153 (36), 140 (100), 124 (36), 99 (75), 81 (50).

[0147] Example 44: (2E,3E)-N-Benzyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide (mixture of isomers) The compound was obtained as a yellow oil (15.1 mmol, 4.50 g, 29% yield) from β-ionone (56.5 mmol, 10.87 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (51.4 mmol, 8.10 g, 1 equiv.) according to the process of Example 1.

[0148] 1 H NMR (400 MHz, CDCl3) δ 7.47 - 7.16 (m, 5H), 6.73 - 6.30 (m, 2H), 5.18 (s, 2H), 2.24 (s, 3H), 2.06 - 1.92 (m, 2H), 1.85 - 1.37 (m, 7H), 1.02 (s, 6H). 13 C NMR (101 MHz, CDCl3) δ 145.51(q), 137.23(q), 135.96(t), 134.45(q), 133.35(t), 132.36(q), 128.87(t), 128.84(t), 128.09(t), 127.69(t), 127.36(t), 125.01(t), 124.14(t), 63.99(d), 39.50(d), 34.16(q), 33.22(d), 29.02(s), 28.87(s), 21.61(s), 18.99(d), 13.50(s). GC / MS (EI): m / z (%): 297 (6) [M + ], 282 (10), 254 (3), 206 (3), 175 (2),158 (8), 105 (10), 91 (100), 65 (9).

[0149] Example 45:N-benzyl-4-((6-methylheptan-2-yl)oxy)butan-1-imine oxide The compound was obtained as a pale yellow oil (14.9 mmol, 4.61 g, 64% yield) from 4-((6-methylheptan-2-yl)oxy)butanal (25.8 mmol, 5.28 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (23.5 mmol, 3.75 g, 1 equiv.) according to the process of Example 1.

[0150] 1 H NMR (400 MHz, CDCl3) δ 7.43 - 7.32 (m, 5H), 6.81 - 6.63 (m, 1H), 4.87 (s, 2H), 3.56 - 3.42 (m, 1H), 3.40 - 3.27 (m, 2H), 2.65 - 2.52 (m, 2H), 1.82 - 1.67 (m, 2H), 1.57 - 1.41 (m, 2H), 1.36 - 1.24 (m, 3H), 1.19 - 1.12 (m, 2H), 1.10 - 1.04 (m, 3H), 0.86 (d, J = 6.4 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 139.41(t), 133.00(q), 129.28(t), 128.90(t), 128.87(t), 75.59(t), 69.14(d), 67.82(d), 39.05(d), GC / MS (EI): m / z (%): 305 (1) [M + ], 193 (1), 176 (3), 162 (3), 149 (8),133 (10), 91 (100), 71 (21), 55 (7).

[0151] Example 46: (1Z,4Z)-N-benzylhept-4-en-1-imine oxide The compound was obtained from hept-4-enal (36.9 mmol, 4.14 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (33.6 mmol, 5.36 g, 1 equiv.) according to the process of Example 1 as a white solid (13.6 mmol, 3.03 g, 41% yield).

[0152] 1 H NMR (400 MHz, CDCl3) δ 7.49 - 7.29 (m, 5H), 6.60 (t, J = 5.8 Hz, 1H), 5.48 - 5.34 (m, 1H), 5.31 - 5.19 (m, 1H), 4.88 (s, 2H), 2.64 - 2.46 (m, 2H), 2.24 (q, J = 7.3 Hz, 2H), 2.06 - 1.85 (m, 2H), 0.92 (t, J = 7.5 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 138.80(t), 133.34(t), 132.88(q), 129.36(t), 128.93(t), 126.99(t), 69.23(d), 26.74(d), 23.04(d), 20.51(d), 14.24(s). GC / MS (EI): m / z (%): 217 (1) [M + ], 188 (2), 158 (1), 149 (2), 132 (2), 104 (3), 91 (100), 77 (4), 65 (18).

[0153] Example 47: (Z)-N-Benzyl-2-((3,7-dimethyloct-6-en-1-yl)oxy)ethane-1-imine oxide The compound was obtained from 2-((3,7-dimethyloct-6-en-1-yl)oxy)acetaldehyde (21.4 mmol, 4.25 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (19.5 mmol, 3.11 g, 1 equiv.) according to the process of Example 1 as a pale yellow solid (13.4 mmol, 4.27 g, 69% yield).

[0154] 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J = 6.2 Hz, 5H), 6.80 (t, J = 4.2 Hz, 1H), 5.14 - 5.03 (m, 1H), 4.88 (s, 2H), 4.40 (d, J = 3.9 Hz, 2H), 3.48 (td, J = 6.7, 3.7 Hz, 2H), 2.02 - 1.89 (m, 2H), 1.67 (s, 3H), 1.63 - 1.55 (m, 4H), 1.27 (d, J = 8.1 Hz, 2H), 1.20 - 1.10 (m, 2H), 0.86 (d, J = 6.6 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 137.94(t), 132.23(q), 131.21(q), 129.60(t), 129.18(t), 129.04(t), 124.67(t), 70.15(d), 69.00(d), GC / MS (EI): m / z (%): 303 (1) [M + ], 234 (2), 207 (1), 164 (2), 145 (2),120 (30), 91 (100), 69 (20), 55 (12).

[0155] Example 48: (1Z,2E,6Z)-N-benzylnona-2,6-dien-1-imine oxide The compound was obtained as a pale yellow solid (11.5 mmol, 2.86 g, 44% yield) from nona-2,6-dienal (28.7 mmol, 4.26 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (26.1 mmol, 3.97 g, 1 equiv.) according to the process of Example 1.

[0156] 1H NMR (400 MHz, CDCl3) δ 7.50 - 7.30 (m, 5H), 7.01 (d, J = 9.4 Hz, 1H), 6.78 (dd, J = 15.9, 9.4 Hz, 1H), 6.30 - 6.11 (m, 1H), 5.49 - 5.18 (m, 2H), 4.95 - 4.77 (m, 2H), 2.28 - 2.20 (m, 2H), 2.20 - 2.10 (m, 2H), 2.06 - 1.95 (m, 2H), 0.93 (t, J = 7.5 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 142.74(t), 136.25(t), 132.74(t), 129.24(t), 128.93(t), 128.88(t), 127.43(t), 121.31(t), 68.97(d), 33.43(d), 26.21(d), 20.56(d), 14.26(s). GC / MS (EI): m / z (%): 243 (9) [M + ], 214 (1), 184 (1), 160 (5), 121 (9), 106 (35), 91 (100), 79 (27), 65 (13).

[0157] Example 49: (1Z,2E)-N-Benzyldodec-2-en-1-imine oxide The compound was obtained as a white solid (12.7 mmol, 3.69 g, 38% yield) from dodec-2-enal (36.3 mmol, 66.20 g, 10% in TEC, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (33.0 mmol, 5.27 g, 1 equiv.) according to the process of Example 1.

[0158] 1H NMR (400 MHz, CDCl3) δ 7.47 - 7.29 (m, 5H), 6.99 (d, J = 9.4 Hz, 1H), 6.81 - 6.68 (m, 1H), 6.28 - 6.10 (m, 1H), 4.88 (s, 2H), 2.19 (q, J = 7.1 Hz, 2H), 1.69 - 1.65 (m, 1H), 1.47 - 1.36 (m, 2H), 1.30 - 1.20 (m, 11H), 0.88 (t, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 143.83(t), 136.41(t), 133.05(q), 129.30(t), 128.96(t), 128.90(t), 120.98(t), 68.94(d), 33.37(d), GC / MS (EI): m / z (%): 287 (1) [M + ], 257 (1), 203 (21), 185 (2), 157 (100),139 (4), 129 (8), 115 (35), 87 (8).

[0159] Example 50: (1Z,2E)-N-Benzyl oct-2-en-1-imine oxide The compound was obtained as a white solid (25.4 mmol, 6.01 g, 88% yield) from oct-2-enal (31.7 mmol, 4.00 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (28.8 mmol, 4.60 g, 1 equiv.) according to the process of Example 1.

[0160] 1H NMR (400 MHz, CDCl3) δ 7.51 - 7.30 (m, 5H), 7.00 (d, J = 9.4 Hz, 1H), 6.85 - 6.62 (m, 1H), 6.30 - 6.10 (m, 1H), 4.88 (s, 2H), 2.19 (q, J = 7.2 Hz, 2H), 1.50 - 1.36 (m, 2H), 1.35 - 1.17 (m, 4H), 0.87 (t, J = 6.7 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 143.74(t), 136.38(t), 133.08(q), 129.27(t), 128.93(t), 128.87(t), 120.99(t), 68.93(d), 33.30(d), 31.34(d), 28.27(d), 22.44(d), 13.97(s). GC / MS (EI): m / z (%): 231 (2) [M + ], 215 (3), 188 (4), 172 (13), 160 (22), 144 (10), 104 (12), 91 (100), 65 (13).

[0161] Example 51: (1Z,2E,6E)-N-Benzyl-3,7-dimethylnona-2,6-dien-1-imine oxide (mixture of diastereoisomers) The compound was obtained as a pale yellow oil (6.9 mmol, 1.90 g, 70% yield) from 3,7-dimethylnona-2,6-dienal (10.8 mmol, 1.80 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (9.8 mmol, 1.57 g, 1 equiv.) according to the process of Example 1.

[0162] 1H NMR (400 MHz, CDCl3) δ 7.50 - 7.31 (m, 5H), 7.26 - 7.17 (m, 1H), 6.61 (d, J = 9.9 Hz, 1H), 5.10 - 4.95 (m, 1H), 4.90 (s, 2H), 2.26 - 2.04 (m, 4H), 2.03 - 1.88 (m, 3H), 1.77 (s, 2H), 1.69 - 1.63 (m, 1H), 1.62 - 1.51 (m, 2H), 0.99 - 0.90 (m, 3H). 13 C NMR (101 MHz, CDCl3) δ 150.17(q), 150.02(q), 149.95(q), 138.49(q), 138.31(q), 138.09(q), 137.85(q), 133.88(t), 133.65(t), 133.41(q), 133.34(q), 129.05(t), 128.87(t), 128.76(t), 122.79(t), 122.50(t), 121.67(t), 121.28(t), 116.74(t), 116.72(t), 115.90(t), 69.11(d), 69.05(d), 40.70(d), 40.43(d), 33.89(d), 33.62(d), 32.32(d), 32.29(d), 26.39(d), 26.21(d), 26.15(d), 25.93(d), 24.77(d), 24.74(d), 24.50(s), 24.47(s), 22.85(s), 18.00(s), 15.94(s), 15.90(s), 12.88(s), 12.81(s), 12.76(s), 12.74(s). GC / MS (EI): m / z (%): 271 (6) [M + ], 256 (2), 189 (12), 174 (33), 149 (17),121 (16), 107 (14), 91 (100), 65 (12).

[0163] Example 52: (Z)-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-(2-methylundecyl)methanimine oxide The compound was obtained from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (7.2 mmol, 1.50 g, 1.1 equiv.) and N-(2-methylundecyl)hydroxylamine (6.5 mmol, 1.29 g, 1 equiv.) according to the process of Example 1 as a pale yellow oil (5.5 mmol, 2.20 g, 84% yield).

[0164] 1 H NMR (400 MHz, CDCl3) δ 6.54 (d, J = 7.2 Hz, 1H), 5.48 - 5.32 (m, 1H), 3.71 - 3.60 (m, 1H), 3.47 - 3.37 (m, 1H), 3.28 - 3.14 (m, 1H), 2.38 - 2.24 (m, 2H), 2.14 - 2.04 (m, 1H), 2.01 - 1.79 (m, 6H), 1.65 - 1.57 (m, 1H), 1.51 - 1.41 (m, 5H), 1.30 - 1.23 (m, 13H), 1.23 - 1.16 (m, 8H), 0.97 - 0.82 (m, 6H). 13 C NMR (101 MHz, CDCl3) δ 143.29(t), 137.78(q), 137.73(q), 118.94(t), 71.80(d), 70.92(q), 43.47(d), 38.05(d), 33.93(d), 31.90(d), 31.05(t), 30.75(t), 29.79(d), 29.59(d), 29.34(q), 29.21(s), 27.87(d), 26.87(d), 26.60(d), 24.86(d), 22.70(d), 22.31(d), 16.93(s), 14.15(s). GC / MS (EI): m / z (%): 393 (1) [M + ], 358 (9), 288 (8), 274 (78), 246 (17), 213 (35), 143 (35), 130 (100), 118 (51).

[0165] Example 53:(1E)-N-Cyclohexyl-9-hydroxy-5,9-dimethyldec-4-en-1-imine oxide The compound was obtained as a pale yellow oil (12.9 mmol, 3.96 g, 77% yield) from 9-hydroxy-5,9-dimethyldec-4-enal (18.3 mmol, 3.69 g, 1.1 equiv.) and N-cyclohexylhydroxylamine (16.6 mmol, 1.88 g, 1 equiv.) according to the process of Example 1.

[0166] 1 H NMR (400 MHz, CDCl3) δ 6.68 (t, J = 5.5 Hz, 1H), 5.12 (m, 1H), 3.76 - 3.56 (m, 1H), 2.63 - 2.45 (m, 2H), 2.28 - 2.16 (m, 2H), 2.07 - 1.94 (m, 4H), 1.91 - 1.80 (m, 4H), 1.75 - 1.64 (m, 3H), 1.62 - 1.53 (m, 2H), 1.51 - 1.40 (m, 4H), 1.37 - 1.25 (m, 3H), 1.20 (s, 6H). 13 C NMR (101 MHz, CDCl3) δ 136.98(q), 136.70(q), 136.64(t), 128.89(t), 123.58(t), 122.92(t), 73.75(t), 70.80(q), 70.72(q), 43.56(d), 43.36(d), 39.90(d), 32.11(d), 31.10(d), 29.27(s), 29.24(s), 26.84(d), 26.71(d), 25.06(d), 25.01(d), 24.00(d), 23.89(d), 23.34(s), 22.61(d), 22.54(d), 16.01(s). GC / MS (EI): m / z (%): 295 (1) [M + ], 280 (7), 208 (31), 192 (10), 178 (12), 141 (14), 122 (15), 95 (21), 55 (100).

[0167] Example 54: (E)-N-Benzyl-3-(3-isopropylphenyl)butan-1-imine oxide The compound was obtained as a pale yellow oil (16.6 mmol, 5.01 g, 88% yield) from 3-(3-isopropylphenyl)butanal (20.7 mmol, 3.93 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (18.8 mmol, 3.01 g, 1 equiv.) according to the process of Example 1.

[0168] 1 H NMR (400 MHz, CDCl3) δ 7.37 - 7.29 (m, 3H), 7.29 - 7.24 (m, 2H), 7.23 - 7.18 (m, 1H), 7.10 - 7.05 (m, 1H), 7.03 - 6.89 (m, 2H), 6.50 (t, J = 5.8 Hz, 1H), 4.80 (s, 2H), 3.09 - 2.95 (m, 1H), 2.91 - 2.79 (m, 2H), 2.77 - 2.67 (m, 1H), 1.29 (d, J = 7.0 Hz, 3H), 1.23 (d, J = 7.0 Hz, 6H). 13 C NMR (101 MHz, CDCl3) δ 149.23(q), 145.48(q), 138.32(t), 132.92(q), 129.13(t), 128.86(t), 128.81(t), 128.55(t), 125.07(t), GC / MS (EI): m / z (%): 295 (1) [M + ], 279 (1), 264 (3), 173 (35), 147 (55),131 (13), 105 (25), 91 (100), 65 (13).

[0169] Example 55: (E)-N-Benzyl-4-(4-hydroxyphenyl)butan-2-imine oxide The compound was obtained as a colorless oil (25.8 mmol, 7.32 g, 28% yield) from 4-(4-hydroxyphenyl)butan-2-one (102 mmol, 16.82 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (93 mmol, 14.86 g, 1 equiv.) according to the process of Example 1.

[0170] 1 H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 7.39 - 7.21 (m, 5H), 6.97 - 6.82 (m, 2H), 6.80 - 6.63 (m, 2H), 5.05 (d, J = 17.3 Hz, 1H), 4.71 (s, 1H), 2.95 - 2.86 (m, 1H), 2.85 - 2.76 (m, 1H), 2.75 - 2.64 (m, 2H), 2.11 (s, 3H). 13 C NMR (101 MHz, CDCl3) δ 156.52(q), 155.77(q), 151.47(q), 151.19(q), 133.48(q), 133.08(q), 130.61(q), 129.28(t), 129.23(t), 128.97(t), 128.88(t), 128.38(t), 128.35(t), 127.79(t), 127.72(t), 116.19(t), 115.72(t), 64.09(d), 63.05(d), 36.75(d), 34.82(d), 32.03(d), 29.72(d), 19.41(s), 18.65(s). GC / MS (EI): m / z (%): 269 (1) [M + ], 253 (13), 238 (4), 162 (8),146 (17), 121 (11), 107 (21), 91 (100), 77(23).

[0171] Example 56: (E)-N-Benzyldec-9-en-1-imine oxide The compound was obtained as a white solid (15.1 mmol, 4.01 g, 80% yield) from dec-9-enal (20.7 mmol, 3.19 g, 1.1 equiv.) and N-benzylhydroxylamine hydrochloride (18.8 mmol, 3.01 g, 1 equiv.) according to the process of Example 1.

[0172] 1 H NMR (400 MHz, CDCl3) δ 7.53 - 7.31 (m, 5H), 6.63 (t, J = 5.8 Hz, 1H), 5.93 - 5.61 (m, 1H), 5.13 - 4.68 (m, 4H), 2.58 - 2.38 (m, 2H), 2.10 - 1.95 (m, 2H), 1.57 - 1.43 (m, 2H), 1.41 - 1.19 (m, 8H). 13 C NMR (101 MHz, CDCl3) δ 139.48(t), 139.07(t), 133.03(q), 129.25(t), 128.91(t), 128.87(t), 114.21(d), 69.17(d), 33.73(d), 29.40(d), 29.08(d), 28.91(d), 28.81(d), 26.73(d), 25.50(d). GC / MS (EI): m / z (%): 259 (1) [M + ], 242 (3), 202 (1), 162 (5), 149 (30),132 (9), 117 (5), 91 (100), 65 (15).

[0173] Example 57: (Z)-1-(4-Methoxyphenyl)-N-(2-methylundecyl)methanimine oxide The compound was obtained from 4-methoxybenzaldehyde (11.5 mmol, 1.57 g, 1.1 equiv.) and N-(2-methylundecyl)hydroxylamine (10.5 mmol, 2.09 g, 1 equiv.) according to the process of Example 1 as a white solid (8.0 mmol, 2.64 g, 76% yield).

[0174] 1H NMR (400 MHz, CDCl3) δ 8.28 - 8.18 (m, 2H), 7.26 (s, 1H), 6.97 - 6.88 (m, 2H), 3.89 - 3.73 (m, 4H), 3.64 - 3.47 (m, 1H), 2.57 - 2.25 (m, 1H), 1.44 - 1.19 (m, 16H), 1.00 - 0.93 (m, 3H), 0.91 - 0.82 (m, 3H). 13 C NMR (101 MHz, CDCl3) δ 160.96(q), 134.29(t), 130.48(t), 123.51(q), 113.83(t), 73.14(d), 55.35(s), 34.14(d), 31.89(d), GC / MS (EI): m / z (%): 319 (10) [M + ], 302 (100), 212 (14), 204 (12), 176 (7),161 (7), 148 (67), 135 (37), 121 (54).

[0175] Example 58: (E)-N-(4-Methoxybenzyl)-2-methylundecane-1-imine oxide The compound was obtained as a white solid (8.2 mmol, 2.62 g, 71% yield) from 2-methylundecanal (12.7 mmol, 2.34 g, 1.1 equiv.) and N-(4-methoxybenzyl)hydroxylamine (11.5 mmol, 1.74 g, 1 equiv.) according to the process of Example 1.

[0176] 1H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 8.5 Hz, 2H), 6.41 (d, J = 7.5 Hz, 1H), 4.79 (s, 2H), 3.82 (s, 3H), 3.15 - 2.95 (m, 1H), 1.42 - 1.18 (m, 16H), 1.04 (d, J = 6.9 Hz, 3H), 0.88 (t, J = 6.8 Hz, 3H). 13 C NMR (101 MHz, CDCl3) δ 160.03(q), 143.86(t), 130.77(t), 125.17(q), 114.31(t), 68.80(d), 55.32(s), 34.03(d), 31.90(d), GC / MS (EI): m / z (%): 319 (1) [M+], 274 (1), 255 (3), 176 (2), 146 (5), 121 (100), 108 (4), 91 (14), 77 (35).

[0177] Example 59: Application in liquid detergent A nitrone precursor (Sample A: (E)-2-methyl-N-(4-methylbenzyl)undecane-1-imine oxide, compound of Example 1) was compared to an aldehyde (Sample B: 2-methylundecanal) in cleaning tests.

[0178] 1) Sample preparation: 0.2 wt. % of precursor or aldehyde was incorporated in an unperfumed liquid detergent base by magnetic stirring at room temperature for 24 h. 2) Washing Test: A 40°C washing machine wash cycle was run using 55g samples of liquid detergent containing the test material and an odor-neutral cotton / elastane blend fabric T-shirt. The wet fabric was line dried and the odor intensity and quality was assessed on a 0 (no odor) to 5 (extremely strong) intensity scale for the freshly dried samples, after 1 day, and after 3 days by a panel of 4-6 experts.

[0179] FIG. 1 shows the evaluation of freshly dried samples (left), after 24 hours (center) and after 4 days (right).

[0180] In Sample B, the aldehyde intensity is relatively high on the freshly dried sample and decreases with time. For Sample A, the intensity increases with time and is highest after 4 days. This example clearly demonstrates the ability of the precursor to release fragrance over an extended period of time.

[0181] Example 60: Further applications in liquid detergents Furthermore, compounds of formula (I) have been tested in liquid detergents. 1) Sample preparation: Test materials at 0.2% wt / wt were incorporated into an unperfumed liquid detergent base with magnetic stirring at room temperature for 24 h. 2) A 40°C washing machine wash cycle was run using 55g liquid detergent samples containing the test material and an odor-neutral cotton / elastane blend fabric T-shirt. The wet fabric was line dried and the odor intensity and quality was assessed after 1 and 3 days by a panel of 4-6 experts on an intensity scale of 0 (no odor) to 5 (extremely strong). Table 1 shows the results of the assessment.

[0182] Table 1: [Table 1]

[0183] The results show that the compounds of the present invention release significant fragrance in various fragrance directions on dry fabrics in liquid detergent applications. The fragrance release occurs over an extended period of time.

[0184] Example 61: Stability Test in Liquid Detergent The stability of (E)-N-isopropyl-2-methylundecane-1-imine oxide (compound of Example 9) in liquid detergent base was assessed by quantitative HPLC with UV detection.

[0185] Liquid wash samples as prepared above containing the test substances were sampled (300 mg diluted in 10 mL acetonitrile / high purity water 1:1) at T0 and after 30 days of storage at 37° C., and the concentrations of precursors were assessed by quantitative HPLC-UV using an external calibration curve. Figure 2 shows the concentration (2a) and recovery (2b) over time.

[0186] After more than a month of storage, the initial concentration of the precursor decreased from 0.21 to 0.18 wt%, meaning that 85% of the precursor was still present in the liquid detergent. The material was determined to be stable in liquid detergent, which is considered a harsh chemical environment due to its composition and alkaline nature.

[0187] Example 62: Application in shampoo 1) Sample preparation: 0.2% wt / wt of (E)-N-isopropyl-2-methylundecane-1-imine oxide (compound of Example 9) was incorporated in an unperfumed shampoo base by magnetic stirring at room temperature for 24 h.

[0188] 2) Washing test: The hair swatches were wetted with warm tap water, then 2 mL of the shampoo sample prepared above was applied to the hair swatches while lathering gently with gloves for 30 seconds. The hair swatches were rinsed with cold tap water for 20 seconds, and excess water was removed by squeezing the hair swatches between two fingers. The hair swatches were allowed to dry in the open air. Their odor intensity and quality were assessed on an intensity scale of 0 (odorless) to 5 (extremely strong) by a panel of 4-6 experts after 1 and 2 days.

[0189] 3) Results: After 1 day, the fragrance score was 3.2, and after 2 days, the fragrance score was 3.3. The perceived odor was described as clean, aldehydic. The results show that the compounds of the present invention release a noticeable fragrance on dry hair upon application of shampoo over an extended period of time.

[0190] Example 63: Biodegradability assessment The results of the biodegradability assessment by manometric respirometry test (OECD Guideline for the testing of materials No. 301F, Paris 1992) are summarised in Table 2.

[0191] Table 2: [Table 2]

[0192] The results show that the compounds of the present invention are generally biodegradable. These results are surprising since many examples of molecules with nitrogen-based functional groups are known to be non-biodegradable. A compound can be classified as biodegradable if it reaches a passing level of 60% of the theoretical oxygen consumption required for mineralization.

[0193] It is readily biodegradable if it reaches a passing level within 10 days of the 28-day test period. The 10-day window begins when the degree of biodegradation reaches 10%. If passing levels are obtained after the 28 day test period, the compound can be classified as inherently biodegradable.

Claims

1. Use of a compound according to formula (I) 【Chemical 1】 as a fragrance precursor for generating a ketone or aldehyde represented by formula (II) when exposed to oxygen and / or water, wherein [Chemical 2] is selected from the group consisting of R 1 is Linear or branched C 1 -C 15 alkyl, for example, C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 alkyl; Linear or branched C 1 -C 15 hydroxyalkyl, alkoxyalkyl and alkylthioalkyl, for example, C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 hydroxyalkyl, 4-(hexyloxy)butyl, 3-(methylthio)propyl; Straight-chain or branched C 2 -C 15 alkenyl, for example, C containing 1, 2, or 3 carbon-carbon double bonds as an example 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 alkenyl; Linear or branched C 2 -C 15 hydroxyalkenyl, for example, C 6 containing 1, 2, or 3 carbon-carbon double bonds, C 7 C 8 C 9 C 10 C 11 C 12 or C 13 such as C 5 -C 14 hydroxyalkenyl; C such as cyclopentyl or cyclohexyl 3 to C 8 cycloalkyl; C 1 to C 7 alkyl (such as ethyl, isopropyl, tert-pentyl), C 2 to C 7 alkenyl (such as isopropenyl), C 1 to C 7 hydroxyalkyl, C2-C7 hydroxyalkenyl and C3-C5 cycloalkyl, substituted with 1, 2, or 3 groups selected from 3 to C 8 cycloalkyl (such as cyclopentyl or cyclohexyl); C 5 ~C 8 Cycloalkenyl (examples include cyclopenta-3-enyl, cyclohex-1-enyl, cyclohex-2,4-dienyl, cycloocta-3-enyl); C 1 to C 7 alkyl (such as ethyl, isopropyl, tert-pentyl), C 2 to C 7 alkenyl (such as isopropenyl), C 1 to C 7 hydroxyalkyl, C 2 to C 7 hydroxyalkenyl and C 3 to C 5 C substituted with 1, 2, or 3 groups selected from cycloalkyl 5 to C 8 cycloalkenyl (such as cyclohex-1-enyl, cyclohex-2,4-dienyl, cycloocta-3-enyl), (such as, R 1 is 7-methyl-spiro[4.5]deca-8-en-6-yl, spiro[4.5]deca-7-en-7-yl, 5,5-dimethylcyclohex-1-enyl, 2,6,6-trimethylcyclohex-1,3-dienyl, 2,4-dimethylcyclohex-3-enyl, or 4-isopropenyl(cyclohex-1-en-1-yl)); (C 1 ~C 3 ) alkyl (C 5 ~C 6 ) cycloalkyl, where the cycloalkyl ring is one group selected from -OH group and =O group, and / or one or two ether group(s), and / or up to 4 C 1 ~C 7 alkyl groups (as an example, R 1 is (3-tert-butylcyclohexyl)ethyl, or (4-(1,1-dimethylpropyl)cyclohexyl)methyl, (3-oxo-2-pentylcyclopentyl)methyl), C 2 ~C 7 alkenyl (such as isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; (C 1 ~C 4 ) alkyl (C 5 ~C 6 ) cycloalkenyl, wherein the cycloalkenyl ring has one -OH group, and / or one or two ether group(s) (singular or plural), and / or up to 4 (i.e., 0, 1, 2, 3, or 4) C 1 ~C 7 alkyl groups (examples include (2,6,6 - trimethylcyclohex - 1 - en - 1 - yl)ethyl, 1 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)butan - 3 - yl), C 2 ~C 7 alkenyl (example is isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; (C 2 ~C 3 ) alkenyl (C 5 ~C 6 ) cycloalkenyl, where the cycloalkenyl ring has one -OH group, and / or one or two ether group(s) (singular or plural), and / or up to 4 (i.e., 0, 1, 2, 3 or 4) C 1 ~C 7 alkyl groups (examples are (2,6,6-trimethylcyclohex-1-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)prop-2-en-2-yl, (2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-2-yl), C 2 ~C 7 alkenyl (example is isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; C 6 to C 14 aryl, such as phenyl or naphthyl; C 6 to C 14 Aryl, where the aryl ring is C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 11 (wherein R 11 is independently selected from hydrogen and C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to 3 (i.e., 0, 1, 2, or 3) groups selected from; (C 1 ~C 4 ) alkyl (C 6 ~C 14 ) aryl, such as benzyl, 2-phenylethyl; (C such as benzyl or 2-phenylethyl 1 ~C 4 )alkyl(C 6 ~C 14 )aryl, where the aryl ring is C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 12 (wherein in the formula R 12 is independently selected from hydrogen and C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to two groups (such as one group) selected therefrom; (C 2 ~C 8 ) alkenyl (C 6 ~C 14 ) aryl, such as 2-phenylethylene-1-yl, 1-phenylhepta-1-en-2-yl; (C 2 to C 8 ) alkenyl (C 6 to C 14 ) aryl, where the aryl ring is C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 13 (wherein in the formula R 13 is independently selected from hydrogen and C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to two groups (such as one group) selected therefrom; C 8 ~C 12 containing a carbon atom, optionally having one CC double bond, C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 14 (wherein R 14 is independently selected from hydrogen and C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is optionally substituted with up to 6 groups selected therefrom, a bicyclic or tricyclic hydrocarbon ring; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, and C 2 to C 5 alkenyl; or or R 1 and R 2 together with the carbon atoms to which they are attached form a 5- to 16-membered hydrocarbon ring, the ring being optionally substituted with C 1 -C 5 alkyl groups (such as methyl, 3-methylbutyl, pentyl), or alkyl acetate groups, for example, R 1 and R 2 together with the carbon atoms to which they are attached form 3-(2-methoxy-2-oxoethyl)-2-pentylcyclopent-1-ylidene, cyclopentadecylidene; R 3 is Linear or branched C 1 ~C 15 alkyl, such as C of methyl, ethyl, propyl, iso-propyl, 2-butyl, 2-methylpentyl, octyl, decyl, dodecyl, 2-methylundecyl, etc. 5 ~C 14 , Linear or branched C 2 ~C 15 alkenyl, such as C of 3-methylbut-2-en-1-yl, etc. 5 ~C 14 ; C which may be arbitrarily substituted 3 ~C 8 cycloalkyl, such as cyclobutyl, cyclopentyl, cyclohexyl, 2-isopropyl-5-methylcyclohexyl, cycloheptyl, cyclooctyl, C 8 ~C 12 A bicyclic or tricyclic hydrocarbon ring containing a carbon atom, for example (1R,5S)-6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)methyl(mirtenyl), and an aromatic residue selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl is selected from the group consisting of said use

2. A compound according to formula (I) [Chemical Formula 3] as a fragrance precursor for generating a ketone or aldehyde represented by formula (II) when exposed to oxygen and / or water, 【Chemical Formula 4】 wherein is selected from the group consisting of R 1 is Linear or branched C 1 -C 15 alkyl, for example, C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 alkyl; Linear or branched C 1 to C 15 hydroxyalkyl, alkoxyalkyl and alkylthioalkyl, for example, C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 to C 14 hydroxyalkyl, 4-(hexyloxy)butyl, 3-(methylthio)propyl; Linear or branched C 2 -C 15 alkenyl, for example, C containing 1, 2, or 3 carbon-carbon double bonds as examples 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 alkenyl; Linear or branched C 2 -C 15 hydroxyalkenyl, e.g., C containing 1, 2, or 3 carbon-carbon double bonds as examples 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 or C 13 such as C 5 -C 14 hydroxyalkenyl; C such as cyclopentyl or cyclohexyl 3 ~C 8 cycloalkyl; C 1 ~C 7 alkyl (such as ethyl, isopropyl, tert-pentyl), C 2 ~C 7 alkenyl (such as isopropenyl), C 1 ~C 7 hydroxyalkyl, C2-C7 hydroxyalkenyl and C3-C5 cycloalkyl, substituted with 1, 2, or 3 groups selected from 3 ~C 8 cycloalkyl (such as cyclopentyl or cyclohexyl); C 5 ~C 8 Cycloalkenyl (examples include cyclopenta-3-enyl, cyclohex-1-enyl, cyclohex-2,4-dienyl, cycloocta-3-enyl); C 1 ~C 7 alkyl (such as ethyl, isopropyl, tert-pentyl), C 2 ~C 7 alkenyl (such as isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl and C 3 ~C 5 C substituted with 1, 2, or 3 groups selected from cycloalkyl 5 ~C 8 cycloalkenyl (such as cyclohex-1-enyl, cyclohex-2,4-dienyl, cyclooct-3-enyl) (for example, R 1 is 7-methyl-spiro[4.5]deca-8-en-6-yl, spiro[4.5]deca-7-en-7-yl, 5,5-dimethylcyclohex-1-enyl, 2,6,6-trimethylcyclohex-1,3-dienyl, 2,4-dimethylcyclohex-3-enyl, or 4-isopropenyl(cyclohex-1-en-1-yl)); (C 1 ~C 3 ) alkyl (C 5 ~C 6 ) cycloalkyl, where the cycloalkyl ring is one group selected from -OH group and =O group, and / or one or two ether group(s), and / or up to 4 C 1 ~C 7 alkyl groups (for example, when R 1 is (3-tert-butylcyclohexyl)ethyl, or (4-(1,1-dimethylpropyl)cyclohexyl)methyl, (3-oxo-2-pentylcyclopentyl)methyl), C 2 ~C 7 alkenyl (for example, isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; (C 1 ~C 4 ) alkyl (C 5 ~C 6 ) cycloalkenyl, where the cycloalkenyl ring has one -OH group and / or one or two ether group(s) (singular or plural) and / or up to four (i.e., 0, 1, 2, 3, or 4) C 1 ~C 7 alkyl groups (e.g., (2,6,6 - trimethylcyclohex - 1 - en - 1 - yl)ethyl, 1 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)butan - 3 - yl), C 2 ~C 7 alkenyl (e.g., isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; (C 2 ~C 3 ) alkenyl (C 5 ~C 6 ) cycloalkenyl, wherein the cycloalkenyl ring has one -OH group and / or one or two ether group(s) (singular or plural) and / or up to 4 (i.e., 0, 1, 2, 3 or 4) C 1 ~C 7 alkyl groups (examples are (2,6,6-trimethylcyclohex-1-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)ethenyl, (2,6,6-trimethylcyclohex-2-en-1-yl)prop-2-en-2-yl, (2,6,6-trimethylcyclohex-1-en-1-yl)prop-2-en-2-yl), C 2 ~C 7 alkenyl (example is isopropenyl), C 1 ~C 7 hydroxyalkyl, C 2 ~C 7 hydroxyalkenyl, and C 3 ~C 5 optionally substituted with cycloalkyl; C 6 ~C 14 Aryl, such as phenyl or naphthyl; C 6 to C 14 aryl, wherein the aryl ring is C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 11 (wherein in the formula R 11 is independently selected from hydrogen and C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to 3 (i.e., 0, 1, 2, or 3) groups selected therefrom; (C 1 to C 4 ) alkyl (C 6 to C 14 ) aryl, such as benzyl, 2-phenylethyl; (C 1 ~C 4 ) alkyl (C 6 ~C 14 ) aryl, wherein the aryl ring is C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 12 (wherein in the formula R 12 is independently selected from hydrogen and C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to two groups (such as one group) selected therefrom; (C 2 ~C 8 ) alkenyl (C 6 ~C 14 ) aryl, such as 2-phenylethylene-1-yl, 1-phenylhepta-1-en-2-yl; (C 2 to C 8 ) alkenyl (C 6 to C 14 ) aryl, where the aryl ring is C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 13 (wherein in the formula R 13 is independently selected from hydrogen and C 1 to C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)) and is substituted with up to 2 groups (such as 1 group) selected therefrom; C 8 ~C 12 containing a carbon atom, optionally having one CC double bond, C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl), -O-CH 2 -O-, and -OR 14 (wherein R 14 is independently selected from hydrogen and C 1 ~C 4 alkyl (such as ethyl, iso-propyl, tert-butyl)), optionally substituted with up to six groups selected from), a bicyclic or tricyclic hydrocarbon ring; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, and C 2 to C 5 alkenyl; or or R 1 and R 2 together with the carbon atoms to which they are attached form a 5- to 16-membered hydrocarbon ring, and the ring is optionally substituted with C 1 -C 5 alkyl groups (such as methyl, 3-methylbutyl, pentyl), or alkyl acetate groups, for example, R 1 and R 2 together with the carbon atoms to which they are attached form 3-(2-methoxy-2-oxoethyl)-2-pentylcyclopent-1-ylidene, cyclopentadecylidene; R 3 is a linear or branched C 1 -C 15 alkyl, such as C 5 -C 14 , Linear or branched C 2 ~C 15 alkenyl, such as C of 3-methylbut-2-en-1-yl, etc. 5 ~C 14 ; C which may be arbitrarily replaced 3 ~C 8 cycloalkyl, such as cyclobutyl, cyclopentyl, cyclohexyl, 2-isopropyl-5-methylcyclohexyl, cycloheptyl, cyclooctyl, C 8 ~C 12 A bicyclic or tricyclic hydrocarbon ring containing a carbon atom, for example (1R,5S)-6,6-dimethylbicyclo[3.1.1]hepta-2-en-2-yl)methyl (myrtenyl), and an aromatic residue selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl; is selected from the group consisting of However, the compound is not 1-(4-hydroxy-3-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-methoxyphenyl)methanimine oxide, N-isopropylnonan-1-imine oxide, 1-(benzo[d][1,3]dioxol-5-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(p-tolyl)methanimine oxide, 1-(3,4-dimethoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-2-methylpropane-1-imine oxide, N-isopropyldecane-1-imine oxide, N-isopropylhexane-1-imine oxide, 1-(furan-2-yl)-N-isopropylmethanimine oxide, N-benzyl-1-(4-methoxyphenyl)methanimine oxide, N-benzyldodecane-1-imine oxide, N-decyldodecane-1-imine oxide, said compound.

3. A method for releasing a ketone or aldehyde represented by formula (II) as defined in claim 1, wherein the compound represented by formula (I) as defined in claim 1 is exposed to oxygen and / or water, said method.

4. A fragrance composition comprising a compound represented by formula (I) as defined in claim 1.

5. A consumer product comprising at least one compound according to formula I as defined in claim 1, and a product base.

6. The consumer product according to claim 5, wherein the consumer product is selected from home care and personal care products.

7. A method for imparting, enhancing, improving or modifying the pleasant properties of a fragrance composition or a consumer product, said method comprising adding at least one compound represented by formula (I) to the composition or the consumer product.

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