Enol ether fragrance precursor

Abstract

The present invention relates to compounds of formula (I) as perfume precursor compounds. In particular, the present invention relates to a method for releasing a compound of formula (I) that is a carbonyl of formula (II), a formate of formula (III), and / or an alcohol of formula (IV) by placing the compound of formula (I) in an environment where it is oxidized. Furthermore, the present invention relates to perfume compositions and consumer perfume products containing at least one compound of formula (I).

Description

[Technical Field]

[0001] The present invention relates to a compound of formula (I) as a fragrance precursor compound. In particular, the present invention relates to a method for releasing a compound which is a carbonyl of formula (II), a formic acid ester of formula (III), and / or an alcohol of formula (IV) by placing a compound of formula (I) in an environment in which it is oxidized. Furthermore, the present invention relates to a fragrance composition and a consumer fragrance product containing at least one compound of formula (I).

[0002] Background of the Invention In the fragrance industry, there is particular interest in compositions or additives that can extend or enhance the fragrance effect of at least one fragrance component over a certain period of time. Long-lasting properties are especially desirable for standard fragrance raw materials that are too volatile, have low persistence, or adhere only in small amounts to the surface of the final use. Furthermore, some fragrance components are unstable and need protection to prevent gradual decomposition before use. Long-lasting fragrances are desired in a variety of applications, such as high-quality or functional fragrances or cosmetics. Washing and softening textile products is a particular area where it is always required that the effects of active substances, especially fragrances or fragrance compositions, remain effective for a certain period after washing, softening, and drying. In fact, many active substances particularly suited to this type of application are known to have poor adhesion to laundry or not remain on laundry during rinsing, resulting in short-lived and less intense fragrance effects. Given the importance of this type of application in the fragrance industry, research in this area has continued, particularly with the aim of finding new and more effective solutions to the aforementioned problems.

[0003] Surprisingly, it has now been found that the enol ether compounds according to the present invention can solve the above-mentioned problems and effectively release compounds that are carbonyl of formula (II), formic acid ester of formula (III), and / or alcohol of formula (IV).

[0004] Detailed Description Olfaction is a complex and dynamic process, and by controlling the release behavior of volatile fragrance compounds, the effects of fragrance formulations can be maximized and the sensory experience can be enriched. Fragrance precursors such as the compounds of the present invention add aspects of control and long-term persistence to the release behavior of highly volatile perfume raw materials (PRMs).

[0005] Without intending to be limited to any particular theory, the compounds of the present invention can achieve their effects on the olfactory properties of fragrance compositions by connecting PRMs to molecular anchors and requiring specific reaction mechanisms under specific environmental conditions to release volatile PRMs from these anchors. In the present invention, the release of one, two, or at most three PRMs is promoted by oxidation when the fragrance precursor comes into contact with oxygen in the ambient air.

[0006] The first problem of the present invention is to obtain from the precursor compound a) a carbonyl compound of formula (II)

Chemical formula

[0007] The terms “active compound,” “active volatile compound,” “active volatile carbonyl, formic acid ester, and / or alcohol,” or similar terms are understood as carbonyl, formic acid ester, and / or alcohol compounds that are capable of providing benefits or effects to the surrounding environment. In particular, “active compound” is selected from the group consisting of fragrance components, flavoring components, odor neutralizing components, antimicrobial components, and insect repellent or insect attractant components. Therefore, in order to be considered an “active compound,” a compound must have at least one property that makes it useful as a fragrance component, odor neutralizing component, flavoring component, antimicrobial component, and / or insect repellent or insect attractant.

[0008] The term “fragrance component” is understood, in its primary purpose, as a compound used as an active ingredient in a fragrance formulation or composition to impart a pleasurable effect. In other words, a compound considered to be a fragrance component must not only have a scent, but also be recognized by those skilled in the fragrance industry as being able to impart or modify the scent of a composition in a positive or pleasant way. Fragrance components may impart additional benefits beyond modifying or imparting a scent, such as long-lasting effect, bloom, odor neutralization, antimicrobial effect, antiviral effect, microbial stability, and pest control. The term “flavoring component” is understood as being able to impart a sense of taste to the palate of the taster. The term “odor neutralizing component” is understood as being able to reduce the perception of malodors, i.e., unpleasant or offensive smells to the human nose. The term “antimicrobial component” is understood as being able to kill microorganisms or reduce or prevent their growth and / or accumulation, and includes antibacterial, antibiotic, antifungal, antiviral, and antiparasitic components. The term "insect attractant or repellent" is understood to refer to compounds that have a positive or negative effect on insects. Examples of insect attractants or repellents can be found in reference texts such as AM El-Sayed, The Pherobase 2005, http: / / www.pherobase.net, or other works of a similar nature.

[0009] According to the above and below embodiments of the present invention, the method according to the present invention is particularly useful when the active compound is a fragrance component, i.e., a fragrance carbonyl compound, formate ester, and / or alcohol. "Fragrance carbonyl compounds, formate esters, and / or alcohols" are compounds used in the fragrance industry, i.e., compounds used as active ingredients in fragrance formulations or compositions to impart a hedonic effect. In other words, such carbonyl compounds, formate esters, and / or alcohols must be recognized by those skilled in the fragrance industry not only as having an odor, but also as being able to impart or modify the odor of a composition in a positive or pleasant way. Fragrance carbonyl compounds, formate esters, and / or alcohols may be of natural or synthetic origin. Many of these combined components are described in either case in reference texts such as the book Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA by S. Arctander, or more recent editions thereof, or other works of similar nature, and in the rich patent literature in the field of fragrances.

[0010] The terms “fragrant carbonyl compounds, formic acid esters, and / or alcohols” as used herein are also referred to as “fragrant compounds.”

[0011] In practice, the present invention is carried out in exactly the same manner regardless of the exact properties of the active carbonyl compound, formic acid ester, or alcohol. Therefore, even if the present invention is described in detail later herein in relation to “aromatic compounds,” it should be understood that the following embodiments are also applicable to other active carbonyl compounds, formic acid esters, and / or alcohols (i.e., the expression “aromatic” can be replaced with “flavoring,” “odor neutralization,” “antibacterial,” “antibiotic,” “insect attractant,” or “insect repellent,” for example).

[0012] The term "optionally" is understood to mean that a particular group that may be optionally substituted may or may not be substituted with a particular substituent. The term "one or more" is understood to mean that the group is substituted with 1 to 7, preferably 1 to 5, and more preferably 1 to 3, particular functional groups.

[0013] The terms “alkyl” and “alkenyl” are understood to include branched and linear alkyl and alkenyl groups. The terms “alkenyl,” “cycloalkenyl,” and “heterocycloalkenyl” are understood to include one, two, or three olefinic double bonds, preferably one or two olefinic double bonds. The terms “cycloalkyl,” “cycloalkenyl,” “heterocycloalkyl,” and “heterocycloalkenyl” are understood to include monocyclic or condensed, spiro and / or crosslinked, bicyclic or tricyclic cycloalkyl, cycloalkenyl, heterocycloalkyl, and heterocycloalkenyl groups, preferably monocyclic cycloalkyl, cycloalkenyl, heterocycloalkyl, and heterocycloalkenyl groups.

[0014] The term "carbonyl" is R 2 Depending on the meaning of the group, it refers to an ester or a ketone; that is, the carbonyl compound of formula (II) is R 2 is OR 2’ It is an ester when it represents R 2 is a hydroxyl group, C 1~3 Alkyl alkyl group, C 1~3 C may be optionally substituted with an alkoxy group. 1~6 Alkyl or C 6~10 It is called a ketone when it represents an aryl group.

[0015] The term "aryl" is understood to include any group containing at least one aromatic group, such as phenyl, indenyl, indanyl, tetrahydronaphthalenyl, or a naphthalenyl group.

[0016] The term "oxo group" is understood to include any group of the formula = O, i.e., groups such as ketones or aldehydes. In other words, C may be optionally substituted by an oxo group. 1~6 Alkyl alkyl groups are alkyl groups having 1 to 6 carbon atoms, and one of these carbon atoms, or even one of the terminal carbon atoms, may be substituted with an =O group instead of two hydrogen atoms.

[0017] For clarity, the phrase "one of its stereoisomers or a mixture thereof" or similar expressions are intended to be understood in the ordinary sense by those skilled in the art, namely that the compound of formula (I) may be a pure enantiomer or a diastereomer. In other words, the compound of formula (I) may have several stereocenters, each of which may have two different stereochemistrys (e.g., R or S). The compound of formula (I) may be in the form of a pure enantiomer, or a mixture of enantiomers or diastereomers. The compound of formula (I) may be a racemic or scalemic compound. Thus, the compound of formula (I) may be a single stereoisomer, or it may be in the form of a composition of various stereoisomers or a substance comprising them.

[0018] According to any one of the above embodiments of the present invention, the compound of formula (I) may be in the form of its E or Z isomer, or a mixture thereof, and for example, the present invention includes a composition of a substance comprising one or more compounds of formula (I) having the same chemical structure but with different arrangements of double bonds. According to a particular embodiment, R 2 is OR 2’ If not expressed, compound (I) may take the form of a mixture comprising isomers E and Z, wherein isomer E constitutes at least 50%, or at least 60%, or at least 70%, or at least 75% of the whole mixture (i.e., mixture E / Z contained in 75 / 25 to 100 / 0). According to another specific embodiment, R 2 is OR 2’When representing, compound (I) may be in the form of a mixture consisting of isomers E and Z, and the isomer Z occupies at least 50%, or at least 60%, or at least 70%, or at least 75% of the whole mixture (that is, the mixture Z / E included in 75 / 25 - 100 / 0).

[0019] According to any one of the embodiments of the present invention, R 1 may be C 3~15 When it may be alkenyl, it is understood that the double bond is not adjacent to the carbon connecting R 1 In other words, the compound of formula (II) is not a conjugated enone, and the compound of formula (I) is not a conjugated dienol ether.

[0020] According to any one of the embodiments of the present invention, the compound of formula (I) is as defined above, provided that: - When R 1 is methyl, R 2 is not methyl, - When R 1 is ethyl, R 2 is not ethyl, - 1,3 - Dimethoxy - 2 - ((2 - phenylprop - 1 - en - 1 - yl)oxy)benzene, 1 - methyl - 4 - ((-2 - methyl - 4 - (2,6,6 - trimethylcyclohex - 1 - en - 1 - yl)buta - 1,3 - diene - 1 - yl)oxy)benzene, 1 - methyl - 4 - ((-2 - methyl - 4 - (2,6,6 - trimethylcyclohex - 2 - en - 1 - yl)buta - 1,3 - diene - 1 - yl)oxy)benzene, and 1,2 - dimethoxy - 4 - (1 - (2 - methoxyphenoxy)prop - 1 - en - 2 - yl)benzene are excluded.

[0021] According to any one of the embodiments of the present invention, n can be 1, 2 or 3. More specifically, n can be 1 or 2.

[0022] According to a specific embodiment of the present invention, R 2 is a hydroxyl group, C 1~3An alkyl group, C 1~3 A C optionally and each independently substituted by an alkoxy group 1~6 May represent an alkyl or phenyl group, in which case R 1 Is C 1~8 Alkyl, C 1~8 Alkoxy, hydroxy, carboxylic acid, and / or C 1~4 An alkyl group optionally and each independently substituted by one or more of carboxylic acid ester groups, C 1~15 Alkyl, C 1~15 Alkoxy, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, carboxylic acid, C 1~4 Carboxylic acid ester, C 6~10 Aryl, and / or C 6~10 An aryl oxy group, in which case C 1~15 Alkyl, C 3~15 Alkenyl, C 6~10 Aryl, C 3~15 Cycloalkyl, or C 5~15 May represent a cycloalkenyl group. R 2 Is a hydroxyl group, C 1~3 An alkyl group, C 1~3 A phenyl group optionally substituted by an alkoxy group or C 1~6 May represent an alkyl group, in which case R 1 Is C 1~8 Alkyl, C 1~8 Alkoxy, C 3~12 Cycloalkyl, C 5~12 Cycloalkenyl, carboxylic acid, C 1~4 Carboxylic acid ester, C 6~10 Aryl, and / or C 6~10 An aryl oxy group, in which case C 1~12 Alkyl, C 3~12 Alkenyl, C 6~10 Aryl, C 3~15 Cycloalkyl or C 5~15 May represent a cycloalkenyl group. R 2 Is C 1~3It may also represent an alkyl group, in which case R 1 C 1~4 Alkyl and / or C 1~4 Phenyl, C, which may be optionally substituted with one or more alkoxy groups. 5~7 Cycloalkyl, and / or C 5~7 C may be optionally substituted with a cycloalkenyl group. 6~10 Aryl or C 1~10 It may also represent an alkyl group. 2 C 1~3 It may also represent an alkyl group, in which case R 1 is phenyl or C 1~10 It may also represent an alkyl group.

[0023] According to a particular embodiment of the present invention, R 2 is OR 2’ It may also represent R 2’ C 1~12 Alkyl alkyl group, C 3~12 It may represent an alkenyl group, a phenethyl group, or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 It may represent an alkoxy group, or two adjacent R groups. 1’ However, when these come together, -O-(CH2) m It may also represent -O-, and m can be 1 or 2. 2 is OR 2’ It may also represent R 2’ C 1~8 Alkyl alkyl group, C 3~8 It may represent an alkenyl group, a phenethyl group, or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3Alkyl alkyl group, C 1~3 It may represent an alkoxy group, or two adjacent R groups. 1’ However, when these come together, -O-(CH2) m It may also represent -O-, and m can be 1 or 2. 2 is OR 2’ It may also represent R 2’ C 1~6 Alkyl alkyl group, C 3~6 It may represent an alkenyl group, a phenethyl group, or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 It may represent an alkoxy group, or two adjacent R groups. 1’ However, when these come together, -O-(CH2) m It may also represent -O-, and m can be 1 or 2. 2 is OR 2’ It may also represent R 2’ C 1~6 Alkyl alkyl group, C 3~6 It may represent an alkenyl group or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 It may also be an alkoxy group. 2 is OR 2’ It may also represent R 2’ C 1~6 It may represent an alkyl group or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3It may also represent an alkoxy group. 2 is OR 2’ It may also represent R 2’ C 1~4 It may represent an alkyl group or a benzyl group, in which case R 1 is one or two R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 It may also represent an alkoxy group. 2 is OR 2’ It may also represent R 2’ C 1~4 It may also represent an alkyl group, in which case R 1 is one R 1’ It may be a phenyl group that is optionally substituted with a group, where R 1’ This may represent a hydroxyl group, a methyl group, or a methoxy group.

[0024] According to a particular embodiment of the present invention, R 1 and R 2 This means that when these come together, C 1~8 Alkyl, C 1~8 Alkoxy, C 3~8 Cycloalkyl, C 5~8 C may be optionally substituted with one or more cycloalkenyl and / or phenyl groups. 5~16 Cycloalkyl or C 5~16 A cycloalkenyl group may be formed. 1 and R 2 This means that when these come together, C 1~6 Alkyl and / or C 1~3 C may be optionally substituted with one or more alkoxy groups. 5~8 Cycloalkyl or C 5~8 A cycloalkenyl group may be formed. 1 and R 2 This means that when these come together, C 1~5C may be optionally substituted with one, two, or three alkyl groups. 5~6 A cycloalkyl group may be formed.

[0025] According to any one embodiment of the present invention, R 3 C simultaneously or independently represents at least one substituent of the aromatic ring. 1~6 C may be optionally substituted with an alkoxy or oxo group. 1~6 Alkyl alkyl group; C 1~3 C may be optionally substituted with an alkyl or methylene group. 4~7 Oxacycloalkyl or oxacycloalkenyl group; C 2~6 Alkenyl group; C 1~6 Alkoxy group; or R b It is an OCO group, and here, R b C is a hydrogen atom. 1~7 Alkyl alkyl group, C 2~7 It is an alkenyl group, a benzyl group, or a phenethyl group.

[0026] According to any one embodiment of the present invention, R 3 This may simultaneously or independently represent at least one substituent of the aromatic ring, hydroxy, C 1~3 C may be optionally substituted with an alkoxy or oxo group. 1~6 Alkyl group; C may be optionally substituted with a methyl or methylene group. 4~7 Oxacycloalkyl or oxacycloalkenyl group; C 2~6 Alkenyl group; C 1~6 Alkoxy group; or R b It is an OCO group, and here, R b C is a hydrogen atom. 1~7 Alkyl alkyl group, C 2~7 Alkenyl group, C 5~7 It is a cycloalkyl group, a benzyl group, or a phenethyl group. 3 These are hydroxy, C, simultaneously or independently. 1~2 C may be optionally substituted with an alkoxy or oxo group. 1~6Alkyl alkyl group; C 2~6 Alkenyl group; C 1~3 Alkoxy group; or R b It may also represent the OCO group, where R b C is a hydrogen atom. 1~7 Alkyl, C 2~7 It may be an alkenyl or cyclohexyl group. 3 C may be optionally substituted with a hydroxyl, methoxy, or oxo group, either simultaneously or independently. 1~4 Alkyl alkyl group; C 2~3 Alkenyl group; or C 1~2 R may represent an alkoxy. 3 R may simultaneously or independently represent a methoxy group, an ethoxy group, a hydroxymethyl group, a methoxymethyl group, a methyl group, a methoxycarbonyl group, a (hex-3-en-1-yloxy)carbonyl group, a propyl group, a propen-1-yl group, a formyl group, a propen-2-yl group, or a 3-oxobutyl group. 3 This group may simultaneously or independently represent a methoxy group, a propyl group, a propen-1-yl group, a formyl group, a propen-2-yl group, or a 3-oxobutyl group.

[0027] According to a particular embodiment, at least two of the compounds of formula (II), (III), and (IV) are active compounds. Furthermore, the compounds of formula (II), (III), and (IV) are active compounds.

[0028] According to certain embodiments, the carbonyl compound of formula (II), the formic acid ester of formula (III), and / or the active alcohol of formula (IV) are fragrance components. It will also be apparent to those skilled in the art that the compounds of formulas (II), (III), and (IV) according to the present invention are essentially volatile compounds.

[0029] Carbonyl compounds, formic acid esters, and / or alcohols can be favorably characterized by a vapor pressure greater than 1.0 Pa, which can be obtained by calculation using the software EPIwin v. 3.10 (2000, available from the U.S. Environmental Protection Agency). According to another embodiment, the vapor pressure of ketones, formic acid esters, and / or alcohols may be greater than 5.0 Pa, or even greater than 7.0 Pa.

[0030] According to certain embodiments, the compound of formula (I) is non-volatile. The compound of formula (I) can be favorably characterized by a vapor pressure of less than 0.01 Pa, which can be obtained by calculation using the software EPIwin v. 3.10 (2000, available from the U.S. Environmental Protection Agency). According to preferred embodiments, this vapor pressure is less than 0.001 Pa.

[0031] According to a particular embodiment, the carbonyl compound of formula (II) is acetophenone, p-methylacetophenone, p-methoxyacetophenone, benzophenone, 1-(5,6,7,8-tetrahydronaphthalene-2-yl)ethane-1-one, 1-(naphthalene-2-yl)ethane-1-one, 1-(naphthalene-1-yl)ethane-1-one, 1-(p-tolyl)propane-1-one, 1-(1,1,2,3,3,6-hexamethyl-2,3-dihydro-1H-inden-5-yl)ethane-1-one, 1-(3,5,5,6,8 ,8-Hexamethyl-5,6,7,8-Tetrahydronaphthalene-2-yl)ethane-1-one, 1-(3-Isopropyl-1,1,2,6-Tetramethyl-2,3-Dihydro-1H-Indene-5-yl)ethane-1-one, 1-(6-(tert-butyl)-1,1-Dimethyl-2,3-Dihydro-1H-Indene-4-yl)ethane-1-one, Acetone, 3-Hexanone, 4-Nonanone, 5-Undecanone, Cyclohexanone, Cyclopentanone, Cyclooctanone, Cycloheptanone, Cyclododecanone, Cyclodecanone 2-butanone, 2-pentanone, 2-hexanone, 2-heptanone, 2-octanone, 2-nonanone, 2-decanone, 2-undecanone, 2-tridecanone, 2-pentadecanone, 3-heptanone, 3-octanone, 5-methyl-3-heptanone, 6-methyl-5-hepten-2-one, 2,6-dimethyl-7-octen-4-one, 2-(sec-butyl)cyclohexane-1-one, 2-(tert-butyl)cyclohexane-1-one, 4-(tert-butyl)cyclohexane-1-one, 4-(tert-pentyl )Cyclohexane-1-one, 5-isopropyl-2-methylcyclohexane-1-one, 2-isopropyl-5-methylcyclohexane-1-one, 2,2,6-trimethylcyclohexane-1-one, 2,2,4-trimethylbicyclo[3.1.1]heptan-3-one, thujanone, 2-ethyl-4,4-dimethylcyclohexane-1-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, plicatone, thujopsan-4-one, 1,3,3-trimethylbicyclo[2.2.1] Heptan-2-one, 4-phenyl-2-butanone, 4-(4-methoxyphenyl)-2-butanone, zingerone, 4-(1,3-benzodioxol-5-yl)-2-butanone, 2-cyclohexyl-4-methyl-2-pentanone, 1-(4-methyl-1-phenoxy)-2-propanone, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-one, 4-(2,6,6-trimethylcyclohex-1-en-1-yl)butan-2-one, (5- E / Z)-6,10-dimethylundeca-5,9-dien-2-one, cyclopentadecanone, (Z)-cycloheptadec-9-en-1-one, 3-methylcyclopentadecane-1-one, 3-methyl-5-cyclopentadecen-1-one, (Z)-cyclopentadec-4-en-1-one, 4,8-cyclododecadiene-1-one, 7-methyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, 7-propyl-2H-benzo[b][1,4]dioxepin-3( 4H)-one, 1-(5-propylbenzo[d][1,3]dioxol-2-yl)ethane-1-one, 4,4a,6,7,8,8a-hexahydro-1,4-methanonaphthalene-5(1H)-one, 2-pentylcyclopentan-1-one, 2-heptylcyclopentan-1-one, 2-(hex-5-en-1-yl)cyclopentan-1-one, 2,2,5-trimethyl-5-pentylcyclopentan-1-one, Iso-E-Super, 1-(5-isopropyl-2-methyl The ketone is selected from the group consisting of tylcyclohex-2-en-1-yl)propan-1-one, 2,2,7,9-tetramethylspiro[5.5]undec-7-en-1-one, 4-ethyl-8-methyloctahydronaphthalene-1(2H)-one, 1-(3,3-dimethylcyclohexyl)ethane-1-one, 2,6,6-trimethylcycloheptan-1-one, and 3,6,8,8-tetramethylhexahydro-1H-3a,7-methanoazulene-5(4H)-one.

[0032] In particular, the carbonyl compound of formula (II) is a ketone selected from the group consisting of acetophenone, 2-undecanone, 3-heptanone, 2-ethyl-4,4-dimethylcyclohexane-1-one, 2-pentylcyclopentan-1-one, and 4-(tert-pentyl)cyclohexane-1-one.

[0033] According to certain embodiments, the carbonyl compound of formula (II) is methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate, pentyl benzoate, hexyl benzoate, heptyl benzoate, (Z)-hex-3-en-1-yl benzoate, isopropyl benzoate, isobutyl benzoate, sec-butyl benzoate, isoamyl benzoate, sec-pentyl benzoate, benzyl benzoate, octyl benzoate, 2-phenylethyl benzoate, 4-methoxybenzoate C 1~4 Alkyl, 4-methylbenzoate C 1~4 C alkyl, 2-methoxybenzoate 1~4 Alkyl, 2-methylbenzoate C 1~4 Alkyl and benzo[d][1,3]dioxol-5-carboxylic acid C 1~4 It is an ester selected from the group consisting of alkyl groups.

[0034] In particular, the carbonyl compound of formula (II) is an ester selected from the group consisting of methyl benzoate, ethyl benzoate, butyl benzoate, hexyl benzoate, octyl benzoate, (Z)-hex-3-en-1-yl benzoate, 2-phenylethyl benzoate, methyl 4-methylbenzoate, and methyl 4-methoxybenzoate.

[0035] According to certain embodiments, the formate ester of formula (III) is 4-allyl-2-methoxyphenyl formate, 2-methoxy-4-(prop-1-en-1-yl)phenyl formate, 2-methoxy-4-propylphenyl formate, 4-formyl-2-methoxyphenyl formate, 2-ethoxy-4-formylphenyl formate, 4-(3-oxobutyl)phenyl formate, 2-methoxyphenyl formate, 4-methylphenyl formate, 2-methylphenyl formate, 4-ethylphenyl formate, 2-ethylphenyl formate, 4-vinylphenyl formate, 2-propylphenyl formate, 2-acetylphenyl formate, 2-meth Xy-4-(3-oxobutyl)phenyl, 2-methoxy-4-methylphenyl formate, 2-methoxy-4-vinylphenyl formate, 4-ethyl-2-methoxyphenyl formate, 2-ethoxy-4-methylphenyl formate, 4-methyl-2-propionylphenyl formate, 2-(formyloxy)-5-methylbenzoate methyl, 2-(formyloxy)-5-methylbenzoate ethyl, 2-ethoxy-4-(methoxymethyl)phenyl formate, 2-methoxy-4-(methoxymethyl)phenyl formate, 2-ethoxy-4-(ethoxymethyl)phenyl formate, 2-methoxy-4-(4-methyl-3,6-Dihydro-2H-pyran-2-yl)phenyl, 2-Methoxy-4-(4-methylenetetrahydro-2H-pyran-2-yl)phenyl formate, 4-(formyloxy)-3-methoxybenzoate methyl, 4-(formyloxy)-3-methoxybenzoate ethyl, 2-(formyloxy)benzoate methyl, 2-(formyloxy)benzoate ethyl, 2-(formyloxy)benzoate isobutyl, 2-(formyloxy)benzoate pentyl, 2-(formyloxy)benzoate isoamyl, 2-(formyloxy)benzoate 2-methylbutyl, 2-(formyloxy)benzoate cyclohexyl, 2-(formyloxy)benzoate (Z)-hex Selected from the group consisting of -3-en-1-yl, 2-(formyloxy)benzoate 4-methylpento-4-en-2-yl, 2-(formyloxy)benzoate phenethyl, 2-(formyloxy)benzoate 3-methyl-2-hexenyl, 2-(formyloxy)benzoate hexyl, 2-(formyloxy)benzoate benzyl, 3-methoxy-5-methylphenyl formate, 2-methoxy-5-(prop-1-en-1-yl)phenyl formate, 2-isopropyl-5-methylphenyl formate, 5-isopropyl-2-methylphenyl formate, 4-(hydroxymethyl)-2-methoxyphenyl formate, and 3-methoxy-5-methylphenyl formate.

[0036] According to a particular embodiment, the alcohol of formula (IV) is eugenol, isoeugenol, dihydroeugenol, vanillin, ethyl vanillin, 4-(4-hydroxyphenyl)butan-2-one, 2-hydroxy-4-methoxybenzaldehyde, 2-methoxyphenol, 4-methylphenol, 2-methylphenol, 4-ethylphenol, 2-ethylphenol, 4-vinylphenol, 2-propylphenol, 3-propylphenol, 1-(2-hydroxyphenyl)ethane-1-one, 4-(4 -Hydroxy-3-methoxyphenyl)butan-2-one, 2-methoxy-4-methylphenol, 2-methoxy-4-vinylphenol, 4-ethyl-2-methoxyphenol, 2-ethoxy-4-methylphenol, 1-(2-hydroxy-5-methylphenyl)propan-1-one, 2-hydroxy-5-methylbenzoate methyl, 2-hydroxy-5-methylbenzoate ethyl, 2-ethoxy-4-(methoxymethyl)phenol, 2-methoxy-4-(methoxymethyl)phenol, 2-ethoxy-4-( Ethoxymethyl)phenol, 2-Methoxy-4-(4-methyl-3,6-dihydro-2H-pyran-2-yl)phenol, 2-Methoxy-4-(4-methylenetetrahydro-2H-pyran-2-yl)phenol, 4-hydroxy-3-methoxybenzoate methyl, 4-hydroxy-3-methoxybenzoate ethyl, methyl salicylate, ethyl salicylate, isobutyl salicylate, pentyl salicylate, isoamyl salicylate, 2-methylbutyl salicylate, cyclohexyl salicylate, (Z)-hex salicylate Selected from the group consisting of -3-en-1-yl, 4-methylpento-4-en-2-yl salicylate, phenethyl salicylate, 3-methyl-2-hexenyl salicylate, hexyl salicylate, benzyl salicylate, 3-methoxy-5-methylphenol, 2-methoxy-5-(prop-1-en-1-yl)phenol, 2-isopropyl-5-methylphenol, 5-isopropyl-2-methylphenol, 4-(hydroxymethyl)-2-methoxyphenol, and 3-methoxy-5-methylphenol.

[0037] In particular, the alcohol of formula (IV) is selected from the group consisting of eugenol, isoeugenol, dihydroeugenol, 4-(4-hydroxyphenyl)butan-2-one, vanillin, (Z)-hex-3-en-1-yl salicylate, methyl salicylate, cyclohexyl salicylate, methyl 4-hydroxy-3-methoxybenzoate, 2-ethoxy-4-(methoxymethyl)phenol, 2-ethoxy-4-methylphenol, and 4-(hydroxymethyl)-2-methoxyphenol and 2-isopropyl-5-methylphenol.

[0038] According to a particular embodiment, the compound of formula (I) is 4-allyl-2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)benzene, 2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)-4-((E)-prop-1-en-1-yl)benzene, 2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)-4-propylbenzene, 4-(4-((2-phenylprop-1-en-1-yl)oxy)phenyl)butan-2-one, 1-((2-ethyl-4,4-dimethylcyclohexylidene) Methoxy)-2-methoxy-4-propylbenzene, 2-methoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 2-methoxy-1-((4-(tert-pentyl)cyclohexylidene)methoxy)-4-propylbenzene, 4-allyl-2-methoxy-1-((4-(tert-pentyl)cyclohexylidene)methoxy)benzene, 4-allyl-2-methoxy-1-((2-methylundec-1-en-1-yl)oxy)benzene, 2-methoxy-1-((2-methylundec-1-en-1-yl)oxy) -4-propylbenzene, 4-(4-((2-ethylhex-1-en-1-yl)oxy)phenyl)butan-2-one, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, 2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)-4-propylbenzene, methyl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate, methyl 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzoate, 2-ethoxy-1-((2-methoxy-2-phenylvinyl)oxy (C)-4-(methoxymethyl)benzene, 2-ethoxy-1-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 2-methoxy-1-((2-methoxy-2-(p-tolyl)vinyl)oxy)-4-propylbenzene, 2-methoxy-1-((2-methoxy-2-(4-methoxyphenyl)vinyl)oxy)-4-propylbenzene, (Z)-hex-3-en-1-yl2-((2-methoxy-2-phenylvinyl)oxy)benzoate, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde,1-((2-butoxy-2-phenylvinyl)oxy)-2-methoxy-4-propylbenzene, 2-methoxy-1-((2-(octyloxy)-2-phenylvinyl)oxy)-4-propylbenzene, 1-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)-2-methoxy-4-propylbenzene, 2-methoxy-1-((2-phenethoxy-2-phenylvinyl)oxy)-4-propylbenzene, 2-ethoxy-1-((2-ethoxy-2-phenylvinyl)oxy)-4-methylbenzene, methyl4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzoate, (4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxyphenyl)methanol, 4-((2- Selected from the group consisting of (hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde, methyl 2-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)benzoate, (Z)-hex-3-en-1-yl 2-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)benzoate, (3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)phenyl)methanol, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 1-isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, and cyclohexyl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate.

[0039] According to any one of the embodiments described above, the carbonyl compound of formula (II), the formic ester of formula (III), and the alcohol of formula (IV) are released from the precursor compound of formula (I) by oxidation of the precursor compound of formula (I) under ambient conditions. Furthermore, the precursor compound of formula (I) is oxidized under ambient conditions and in the absence of a catalyst. For clarity, “ambient conditions” or similar expression is intended to be in the ordinary sense understood by those skilled in the art, i.e., oxidation is intended to occur at room temperature, in air, and at atmospheric pressure. In other words, the environment in which the compound is oxidized is air. Thus, it is understood that the compound of formula (I) is oxidized in ambient air. In particular, it is understood that the compound of formula (I) does not require a pure oxygen environment, heat, or a catalyst to be oxidized.

[0040] While not intended to be limited to any particular theory, the rate at which the precursor compound of formula (I) is oxidized may be greater than, equal to, or slower than the evaporation rates of the carbonyl compound of formula (II), the formic acid ester of formula (III), or the alcohol of formula (IV).

[0041] In some embodiments, the rate at which the precursor compound of formula (I) is oxidized, and thereby the rate at which each of the carbonyl compound of formula (II), the formate ester of formula (III), or the alcohol of formula (IV) is released, enhances or prolongs the diffusion effect and / or perception of the characteristic aroma of at least one carbonyl compound of formula (II), at least one formate ester of formula (III), and / or at least one alcohol of formula (IV) as defined above.

[0042] In one embodiment, 100% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 90% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 80% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 70% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 60% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 50% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 40% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 30% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 20% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 10% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 9% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 8% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 7% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 6% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 5% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 4% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 3% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 2% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours. Alternatively, 1% of the compound of formula (I) is oxidized in ambient air over a period of 24 to 48 hours.

[0043] In certain embodiments, the compound of formula (I) is encapsulated. The compound of formula (I) can be encapsulated in a microcapsule. In a preferred embodiment, the compound of formula (I) is encapsulated in a core-shell microcapsule, where the compound of formula (I) is contained within a core surrounded by a shell. The shell of the microcapsule protects the compound of formula (I) from the environment. The shell is made of a material capable of releasing the compound of formula (I), as well as / or the compounds of formulas (II), (III), and / or (IV). In a preferred embodiment, the shell is made of a material capable of releasing the compound of formula (I), as well as / or the compounds of formulas (II), (III), and / or (IV), upon rupture of the shell and / or by diffusion through the shell. Those skilled in the art are well aware of the methods for manufacturing such microcapsules. Therefore, a microcapsule containing at least one compound of formula (I) is one of the objectives of the present invention.

[0044] In a preferred embodiment, encapsulation of the compound of formula (I) can provide an intracapsule environment in which all or part of the compound of formula (I) can be oxidized, thereby releasing the respective ketone of formula (II), the formate ester of formula (III), or the alcohol of formula (IV) into the capsule. In a preferred embodiment, the shell of the microcapsule can function as a permeable barrier to prevent the respective carbonyl compound of formula (II), the formate ester of formula (III), or the alcohol of formula (IV) from leaking out of the capsule.

[0045] In a second aspect, the present invention relates to methods for imparting, enhancing, improving, or modifying the olfactory properties of a fragrance composition, the air surrounding a fragrance composition, a surface, or a fragranced article, comprising adding an effective amount of at least one compound of formula (I) as defined above to a composition, air, or article, or contacting or treating a surface with an effective amount of at least one compound of formula (I) as defined above. As used herein, the term “surface” may refer to the user’s skin, hair, textiles, or hard surface on which a fragrance composition containing at least one compound of formula (I) is applied.

[0046] In a third aspect, the present invention relates to a method for enhancing or extending the diffusion effect of the characteristic aroma of at least one carbonyl compound of formula (II), at least one formic acid ester of formula (III), and / or at least one alcohol of formula (IV) as defined above, in the air surrounding a surface or fragrance composition, wherein the surface or air is treated with at least one compound (I) as defined above, or with a composition or article containing at least one compound (I), under conditions that allow the surface or air to release at least one carbonyl compound of formula (II), at least one formic acid ester of formula (III), and / or at least one alcohol of formula (IV) over time.

[0047] Furthermore, the present invention is i) At least one compound of formula (I) as defined above; ii) At least one component selected from the group consisting of fragrance carriers and fragrance bases; and iii) At least one optional fragrance enhancer; This relates to a fragrance composition containing [a specific ingredient / component].

[0048] In this specification, "fragrance carrier" means a material that is substantially neutral from the standpoint of fragrance, that is, a material that does not significantly alter the sensory properties of the fragrance components. The carrier may be a liquid or a solid.

[0049] Examples of liquid carriers, though not limited to specific examples, include emulsions, i.e., systems of solvents and surfactants, or solvents commonly used in fragrances. It is not possible to provide a comprehensive detailed description of the properties and types of solvents commonly used in fragrances. However, examples of solvents that are most commonly used include butylene or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2,3-propanetriyltriacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropane-2-ylacetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethano, triethyl citrate, or mixtures thereof. For compositions containing both a fragrance carrier and a fragrance base, suitable fragrance carriers other than those specified above may include ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known by the trademark Isopar® (supplied by Exxon Chemical), glycol ethers and glycol ether esters such as those known by the trademark Dowanol® (supplied by Dow Chemical Company), or hydrogenated castor oil such as those known by the trademark Cremophor® RH 40 (supplied by BASF).

[0050] The term "solid carrier" is intended to refer to a material to which a fragrance composition or some elements of a fragrance composition can be chemically or physically bound. Generally, such solid carriers are used to stabilize a composition or to control the evaporation rate of a composition or some of its components. The use of solid carriers is currently practiced in the art, and those skilled in the art are familiar with the methods for achieving the desired effects. However, non-limiting examples of solid carriers include absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood-based materials, organic or inorganic gels, clays, gypsum talc, or zeolites.

[0051] Other non-limiting examples of solid supports include encapsulating materials. Examples of such materials may include wall-forming and plasticizing materials such as monosaccharides, disaccharides, or trisaccharides, natural or modified starches, hydrophilic colloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins, or pectin, or materials listed in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitaet, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a process well known to those skilled in the art and can be carried out, for example, by using techniques such as spray drying, agglomeration, or even extrusion; or it may consist of coating encapsulation such as coacervation and composite coacervation techniques.

[0052] Non-limiting examples of solid supports include core-shell capsules using aminoplast, polyamide, polyester, polyurea, or polyurethane type resins or mixtures thereof (all of which are well known to those skilled in the art), particularly using techniques such as polymerization, interfacial polymerization, coacervation, or phase separation processes induced by all of these together (all of which are described in the prior art), in the presence of a polymeric stabilizer or cationic copolymer, optionally.

[0053] The resin can be produced by polycondensation of an aldehyde (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid, or glycolaldehyde, and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylolmelamine, methylated methylolmelamine, guanazole, and mixtures thereof. Alternatively, pre-molded alkylolated polyamines, such as those commercially available as trademarks Urac® (supplied by Cytec Technology Corp.), Cymel® (supplied by Cytec Technology Corp.), Urecoll®, or Luracoll® (supplied by BASF), can be used.

[0054] Another resin is obtained by polycondensation of a polyol such as glycerol with a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylene diisocyanate, or a biuret of hexamethylene diisocyanate or a trimer of xylene diisocyanate, and trimethylolpropane (known by the trademark Takenate®; supplied by Mitsui Chemicals), in particular by polycondensation of a trimer of xylene diisocyanate with trimethylolpropane and a biuret of hexamethylene diisocyanate.

[0055] Some influential literature on the polycondensation of amino resins, specifically the polycondensation of melamine resins with aldehydes for encapsulating fragrances, includes papers such as K. Dietrich et al. Acta Polymerica, 1989, vol. 40, pages 243, 325, and 683, and 1990, vol. 41, page 91. Such papers already describe various parameters affecting the production of such core-shell microcapsules according to prior art methods, which are further described and illustrated in patent documents. U.S. Patent No. 4,396,670 by Wiggins Teape Group Limited is an early example of the latter. Since then, many other authors have enriched the literature in this field, and it is considered impossible to cover all published developments herein; however, fundamental knowledge of encapsulation technology is extremely important. Appropriate and more recent publications disclosing the appropriate use of such microcapsules include, for example, the article in HYLee et al. Journal of Microencapsulation, 2002, vol. 19, pages 559-569 and International Patent Application No. 01 / 41915, as well as the article in S. Bone et al. Chimia, 2011, vol. 65, pages 177-181.

[0056] The term "fragrance base" is understood to refer to a composition containing at least one fragrance-enhancing component.

[0057] Fragrance-enhancing components are not compounds according to the present invention. Furthermore, the term “fragrance-enhancing component” is understood to be a compound used in a fragrance formulation or composition to impart a pleasurable effect. In other words, an auxiliary component considered to be fragrance-enhancing must not only have a scent, but also be recognized by those skilled in the art as being able to impart or modify the scent of a composition in a positive or pleasant way.

[0058] While this specification does not guarantee a more detailed description of the properties and types of fragrance-enhancing components present in the base, and is not exhaustive in any way, those skilled in the art can select them based on their basic knowledge and according to the intended use or application and the desired sensory stimulation effect. Generally, these fragrance-enhancing components belong to a diverse chemical classification, including alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogen or sulfur heterocyclic compounds, and essential oils, and may be of natural or synthetic origin.

[0059] In particular, the following are some commonly used fragrance-enhancing ingredients in fragrance formulations: - Aldehyde components: decanal, dodecanal, 2-methyl-undecinal, 10-undecenal, octanal, nonanal, and / or nonenal; - Aromatic herbal components: Eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxatian, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol, and / or alpha-pinene; - Balsam components: Coumarin, ethyl vanillin, and / or vanillin; - Citrus components: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpene, limonene, 1-p-menthen-8-yl acetate, and / or 1,4(8)-p-mentadiene; - Floral components: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta-ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen- 1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6-trimethyl-3-cyclohexen-1 -Carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, verzyl acetate, geraniol, p-ment-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis-dihydrojasmonate methyl, 3- Methyl-5-phenyl-1-pentanol, verzylpropionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl(S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexen-1-carbaldehyde, amyl cinnamaldehyde, 8-decene-5-olido, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl, berzyl isobutyrate, and / or a mixture of methyl ionone isomers; - Fruity components: Gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxatian, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolan-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxyranyl]acetate, and / or diethyl 1,4-cyclohexanedicarboxylate; - Green components: 2-methyl-3-hexanone(E)-oxime, 2,4-dimethyl-3-cyclohexen-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styraryl acetate, allyl(2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol, and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; - Musk components: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecene-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecene-2-one, 1-oxa-13-cyclohexadecene-2-one, (9Z)-9-cycloheptadecene-1-one, 2-{(1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate, 3-methyl-5-cyclopene Tadecene-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one, and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; - Woody components: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxiran-2,9'-tricyclo[6.2.1.0 2,7 Undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-ene-1-ylacetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, patchouli oil, terpene fraction of patchouli oil, clearwood(registered trademark), (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopentene-1' -yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methylcedyl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-2-yl)ethane-1-one, and / or isobornyl acetate; - Other ingredients (e.g., amber, powdery spicy, or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any stereoisomers thereof, heliotropin, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, and / or 3-(3-isopropyl-1-phenyl)butanal.

[0060] The fragrance base according to the present invention is not limited to the above-mentioned fragrance auxiliary components, and many other such auxiliary components are described in reference texts such as S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA or a more recent edition thereof, or other works of similar nature, and in the extensive patent literature in the field of fragrances. It is also understood that the auxiliary components may be compounds known to release various types of fragrance compounds in a controlled manner.

[0061] The term "fragrance additives" is understood to refer to ingredients that can impart additional benefits such as color, specific lightfastness, and chemical stability. While it is not possible to provide a comprehensive detailed description of the properties and types of additives commonly used in fragrance bases, it should be noted that the ingredients are well known to those skilled in the art. However, specific, non-limiting examples include: viscosifiers (e.g., surfactants, thickeners, gelling agents, and / or rheological modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light and / or buffering or chelating agents, e.g., BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin coolants, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0062] Those skilled in the art will understand that by simply applying standard knowledge in the art and by trial and error methodologies, the optimal formulation for the desired effect can be perfectly designed by mixing the aforementioned components of a fragrance composition.

[0063] A composition of the present invention comprising at least one compound of formula (I) and at least one fragrance carrier represents a specific embodiment of the present invention and represents a fragrance composition containing at least one compound of the present invention, at least one fragrance carrier, at least one fragrance base, and at least one optional fragrance auxiliary.

[0064] It is useful to note herein that the possibility of having two or more compounds of the present invention or other precursors of similar types in the above-described composition is important because it enables perfumers to prepare accords and fragrances having the scent characteristics of various compounds of the present invention, thereby enabling the formation of new building blocks for creative purposes.

[0065] For clarity, it should be noted that any mixture obtained directly from chemical synthesis, such as an unpurified reaction medium in which the compounds of the present invention are thought to be present as a starting material, intermediate, or final product, cannot be considered a fragrance composition according to the present invention unless the mixture provides the compounds of the present invention in a form suitable for fragrance. Therefore, unless otherwise specified, unpurified reaction mixtures are generally excluded from the present invention.

[0066] Furthermore, the compounds of the present invention can also be advantageously used in all fields of modern fragrances, i.e., high-quality or functional fragrances, to positively impart or modify the scent of consumer products to which compound (I) is added. Accordingly, the present invention also relates to fragranced consumer products containing at least one compound of formula (I) as defined above or a fragrance composition as defined above.

[0067] For clarity, it should be noted that the term “fragrance-containing consumer product” is understood to mean a consumer product that is expected to produce at least a pleasant fragrance effect on the surface to which it is applied (e.g., skin, hair, textiles, or hard surfaces). In other words, the fragrance-containing consumer product according to the present invention is a fragrance-containing consumer product that contains a functional formulation, as well as additional beneficial agents corresponding to an optional desired consumer product, such as a conditioner, detergent, or deodorant, and at least one compound of the present invention in an olfactory-effective amount. For clarity, fragrance-containing consumer products are non-edible products.

[0068] The properties and types of components in fragranced consumer products are not guaranteed to be described in more detail herein and are not exhaustive in any case; those skilled in the art can select them based on their general knowledge, the properties of the product, and the desired effect.

[0069] In one embodiment, the fragranced consumer product is a perfume, fabric care product, body care product, cosmetic, skin care product, air care product, or home care product.

[0070] Appropriate fragranced consumer products include, but are not limited to, perfumes such as fine perfumes, splashes or eau de perfumes, colognes or shave or aftershave lotions; fabric care products such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, fabric refreshers, ironing waters, paper, bleach, carpet cleaners, and curtain care products; body care products such as hair care products (e.g., shampoos, coloring preparations or hairsprays, color care products, hair styling products, dental care products), disinfectants, and intimate care products; and cosmetics (e.g., skin creams or lotions, vanishing creams or deodorants or antiperspirants (e.g., sprays or roll-ons)). Examples include hair removal agents, sunscreens or sunscreens or after-sun products, nail products, skin cleansers, cosmetics; or skincare products (e.g., soaps, shower or bath mousses, oils or gels, or hygiene products or foot / hand care products); air care products such as deodorizers or "ready-to-use" powdered air fresheners for use in household spaces (rooms, refrigerators, cupboards, shoes, or cars) and / or public spaces (halls, hotels, malls, etc.); or home care products such as mold removers, furniture care products, wipes, dish soap or hard surface cleaners (e.g., for floors, bathrooms, toilets, or windows); leather care products; and car care products such as polishes, waxes, or plastic cleaners.

[0071] Typical examples of laundry detergent or fabric softener compositions that may incorporate the compounds of the present invention are described in International Publication No. 97 / 34986, U.S. Patent Nos. 4,137,180 and 5,236,615, or European Patent No. 7,998,85. Other typical detergent and fabric softener compositions that can be used are described in publications such as Ullmann's Encyclopedia of Industrial Chemistry, Vol. 20, Wiley-VCH, Weinheim, pp. 355-540 (2012); Flick, Advanced Cleaning Product Formulations, Noye Publication, Park Ridge, New Jersey (1989); Showell, in Surfactant Science Series, vol. 71: Powdered Detergents, Marcel Dekker, New York (1988); and Proceedings of the World Conference on Detergents (4th, 1998, Montreux, Switzerland), AOCS print.

[0072] The proportions in which the compounds according to the present invention can be incorporated into the various articles or compositions described above vary within a wide range of values. These values ​​depend on the properties of the article or product to be scented, the desired olfactory effect, and the properties of the co-components in a given composition when the compounds according to the present invention are mixed with fragrance co-components, solvents, or additives commonly used in the art.

[0073] For example, a typical concentration of the compound of the present invention is 0.001% to 10% by weight, or more, based on the weight of the composition in which it is formulated. In the case of consumer products containing fragrances, a typical concentration of the compound of the present invention is approximately 0.001% to 5% by weight, or more, based on the weight of the consumer product in which it is formulated.

[0074] Furthermore, the present invention relates to a compound of formula (I). Therefore, another object of the present invention is a compound of formula (I) below in the form of one of its stereoisomers or a mixture thereof: [ka] [In the formula, R 2 is OR 2’ Represents R 2’ C 1~12 Alkyl alkyl group, C 3~12 When representing an alkenyl group, phenethyl group, or benzyl group, R 1 is one or two R 1’ A phenyl group which may be optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 Alkoxy group, or R a COO group, R a Represents an OCO group, R a C is a hydrogen atom. 1~3 Alkyl alkyl group, C 2~3 It is either an alkenyl group or two adjacent R groups. 1’ However, when these come together, -O-(CH2) m -O- represents -O-, where m is 1 or 2, or C 5~6 Forms a saturated or unsaturated ring; R 2 C 1~3 When representing an alkyl group, R 1 C 1~8 Alkyl, C 1~8 Alkoxy, hydroxy, carboxylic acid, and / or C 1~4 C may be optionally substituted with one or more carboxylic acid ester groups. 1~15 Alkyl, C 1~15 Alkoxy, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, carboxylic acid, C 1~4 Carboxylic acid ester, C 6~10 Aryl, and / or C 6~10C may be optionally substituted with one or more aryloxy groups. 1~15 Alkyl, C 2~15 Alkenil, C 6~10 Ariel, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, or C 3~14 Represents a heterocycloalkyl group; or R 1 and R 2 This means that when these come together, C 1~8 Alkyl, C 1~8 Alkoxy, carboxylic acid, and / or C 1~4 C may be optionally substituted with one or more carboxylic acid ester groups. 1~15 Alkyl, C 1~15 Alkoxy, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, C 6~10 Aryl, and / or C 6~10 C may be optionally substituted with one or more aryloxy groups. 5~16 Cycloalkyl, C 5~16 Cycloalkenyl, C 4~14 Heterocycloalkyl, or C 4~14 It forms a heterocycloalkenyl group, where the heteroatom represents one or more oxygen atoms; n represents an integer between 1 and 3; R 3 C simultaneously or independently represents at least one substituent of the aromatic ring. 1~6 C may be optionally substituted with an alkoxy or oxo group. 1~6 Alkyl alkyl group, C 2~6 Alkenyl group, C 1~6 Alkoxy group, or R b It is an OCO group, and here, R b C is a hydrogen atom. 1~7 Alkyl alkyl group, C 2~7 Alkenyl group, C 3~7 [It is a cycloalkyl group, a benzyl group, or a phenethyl group]; And, - R1 If it is methyl, then R 2 It is not methyl, - R 1 If it is ethyl, then R 2 It is not ethyl, - 1,3-dimethoxy-2-((2-phenylprop-1-en-1-yl)oxy)benzene, 1-methyl-4-((-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)oxy)benzene, 1-methyl-4-((-2-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)buta-1,3-dien-1-yl)oxy)benzene, and 1,2-dimethoxy-4-(1-(2-methoxyphenoxy)prop-1-en-2-yl)benzene are excluded. It is a compound of formula (I) given the following condition.

[0075] In a further embodiment, the present invention is a) Carbonyl compound of formula (II) [ka] [In the formula, R 2 is OR 2’ Represents R 2’ C 1~6 Alkyl alkyl group, C 2~6 When representing an alkenyl group or a benzyl group, R 1 is one or two R 1’ A phenyl group which may be optionally substituted with a group, where R 1’ The hydroxyl group, C, is present simultaneously or independently. 1~3 Alkyl alkyl group, C 1~3 Alkoxy group, R a COO group, R a Represents an OCO group, R a C is a hydrogen atom. 1~3 Alkyl alkyl group, C 2~3 It is either an alkenyl group or two adjacent R groups. 1’ However, when these come together, -O-(CH2) m-O- represents -O-, where m is 1 or 2, or C 5~6 Forms a saturated or unsaturated ring; R 2 is a hydroxyl group, C 1~3 Alkyl alkyl group, C 1~3 C may be optionally substituted with alkoxy groups. 1~6 Alkyl or C 6~10 When representing an aryl group, R 1 C 1~8 Alkyl, C 1~8 Alkoxy, hydroxy, carboxylic acid, and / or C 1~4 C may be optionally substituted with one or more carboxylic acid ester groups. 1~15 Alkyl, C 1~15 Alkoxy, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, carboxylic acid, C 1~4 Carboxylic acid ester, C 6~10 Aryl, and / or C 6~10 C may be optionally substituted with one or more aryloxy groups. 1~15 Alkyl, C 2~15 Alkenil, C 6~10 Ariel, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, or C 3~14 Represents a heterocycloalkyl group; or R 1 and R 2 This means that when these come together, C 1~8 Alkyl, C 1~8 Alkoxy, carboxylic acid, and / or C 1~4 C may be optionally substituted with one or more carboxylic acid ester groups. 1~15 Alkyl, C 1~15 Alkoxy, C 3~15 Cycloalkyl, C 5~15 Cycloalkenyl, C 6~10 Aryl, and / or C 6~10 C may be optionally substituted with one or more aryloxy groups. 5~16Cycloalkyl, C 5~16 Cycloalkenyl, C 4~14 Heterocycloalkyl or C 4~14 It forms a heterocycloalkenyl group, where the heteroatom represents one or more oxygen atoms. b) Formate ester of formula (III) [ka] [In the formula, n represents an integer between 1 and 5; R 3 It simultaneously or independently represents at least one substituent of the aromatic ring, hydroxy, C 1~6 C may be optionally substituted with an alkoxy or oxo group. 1~6 Alkyl alkyl group; C 1~3 C may be optionally substituted with an alkyl or methylene group. 4~7 Oxacycloalkyl or oxacycloalkenyl group; C 2~6 Alkenyl group; C 1~6 Alkoxy group; or R b It is an OCO group, and here, R b C is a hydrogen atom. 1~7 Alkyl alkyl group, C 2~7 Alkenyl group, C 3~7 [It is a cycloalkyl group, a benzyl group, or a phenethyl group]; c) Alcohol of formula (IV) [ka] [In the formula, R3 has the same meaning as defined above]; The use of a precursor compound for releasing a compound selected from the group consisting of, At least one of the compounds of formula (II), (III), or (IV) is the active compound; The precursor compound is a compound of formula (I). [ka] [where n, R 1 , R 2 , and R3 [This includes the same meaning as defined above]; The aforementioned release also relates to uses that occur when the precursor compound of formula (I) is placed in an environment in which the compound is oxidized, i.e., under ambient conditions.

[0076] In further embodiments, the present invention relates to the use of at least one compound of formula (I) as defined above to impart, enhance, improve, or modify the olfactory properties of a fragrance composition, the air surrounding a fragrance composition, a surface, or a fragranced article, including adding an effective amount of at least one compound of formula (I) as defined above to a composition or article, or contacting or treating a surface with an effective amount of at least one compound of formula (I) as defined above. As used herein, the term “surface” may refer to the user’s skin, hair, textiles, or hard surface on which a fragrance composition containing at least one compound of formula (I) is applied.

[0077] In a further embodiment, the present invention relates to the use of at least one compound of formula (I) as defined above to enhance or extend the diffusion effect and / or perception of the characteristic aromas of at least one carbonyl compound of formula (II) as defined above, at least one formic acid ester of formula (III), and / or at least one alcohol of formula (IV) on a surface, wherein the surface is treated with at least one compound of formula (I) as defined above, or with a composition or article containing at least one compound of formula (I), under conditions that allow the surface to release at least one carbonyl compound of formula (II), at least one formic acid ester of formula (III), and / or at least one active alcohol of formula (IV) over time.

[0078] Examples The present invention will now be described in more detail by the following examples, where abbreviations have their usual meanings in the art, and temperatures are given in degrees Celsius (°C). The NMR spectrum is 400 MHz ( 1 H) and 100MHz ( 13Bruker Avance II Ultrashield 400 plus operating at C) or 500MHz ( 1 H) and 125MHz ( 13 C) Bruker Avance III 500 or 600MHz ( 1 H) and 150MHz ( 13 Spectra were acquired using one of the Bruker Avance III 600 cryoprobes operating in C). The spectra were internally referenced to tetramethylsilane 0.0 ppm. 1 The 1H NMR signal shift was expressed in δppm, and the binding constant (J) was expressed in Hz using the following multiplicities: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), b (b) (indicating unseparated binding), and interpreted using Bruker Topspin software. 13 The ¹¹C NMR data are expressed as chemical shifts δppm and hybridization from DEPT 90 and DEPT 135 experiments, with C being quaternary; CH being methine; CH2 being methylene; CH3 being methyl.

[0079] Example 1 Synthesis of a compound according to formula (I) that releases a carbonyl compound of formula (II), which is a ketone. General experimental section for compounds 1-7 Dimethyl acetal (3 equivalents) was combined with phenol (1 equivalent) and KHSO4 (0.12-0.15 equivalents) in a round-bottom flask (100 mL) equipped with a distillation head and a nitrogen bubbler. The mixture was carefully placed into an oil bath preheated to 175°C. The oil bath temperature was maintained for approximately 10-20 minutes to allow methanol to be vigorously distilled first, after which the temperature was raised to 220°C while continuing to remove methanol. After heating for 3-4 hours, the mixture was removed from the oil bath and Na2CO3 (2 g) was added. The resulting enol ether was isolated by short-pass vacuum distillation from the reaction flask.

[0080] Compound 1. Starting with 4-allyl-2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)benzene:eugenol (10 g, 61 mmol), dimethyl acetal of 2-phenylpropanal (32.9 g, 183 mmol), and KHSO4 (0.996 g, 7.31 mmol), the title compound (10.71 g, 38.2 mmol) was isolated in 63% yield as a pale yellow oily substance by distillation (bp 160-165°C, 3.3 Pa) (E / Z = 78:22). [ka]

[0081] Starting with compound 2.2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)-4-((E)-prop-1-en-1-yl)benzene:isoeugenol (10 g, 61 mmol), dimethyl acetal of 2-phenylpropanal (32.9 g, 183 mmol), and KHSO4 (0.996 g, 7.31 mmol), the title compound (8.34 g, 29.7 mmol) was isolated in 41% yield as a pale yellow oily substance by distillation (bp 170-180°C, 3.3 Pa) (E / Z = 78:22). [ka]

[0082] Starting with compound 3.2-methoxy-1-((2-phenylprop-1-en-1-yl)oxy)-4-propylbenzene:dihydroeugenol (10 g, 60 mmol), dimethyl acetal of 2-phenylpropanal (32.5 g, 180 mmol), and KHSO4 (0.984 g, 7.23 mmol), the title compound (13.6 g, 48.3 mmol) was isolated in 80% yield as a pale yellow oily substance by distillation (bp 145-155°C, 3.3 Pa) (E / Z = 78:22). [ka]

[0083] Starting with compound 4.4-(4-((2-phenylprop-1-en-1-yl)oxy)phenyl)butan-2-one:4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) (10 g, 61 mmol), dimethyl acetal of 2-phenylpropanal (32.9 g, 183 mmol), and KHSO4 (0.996 g, 7.31 mmol), the title compound (6.07 g, 21.6 mmol) was isolated in 36% yield as a pale yellow oily substance by distillation (bp>180°C, 3.3 Pa) (E / Z=78:22). [ka]

[0084] Starting with compound 5.4-allyl-2-methoxy-1-((2-methylundec-1-en-1-yl)oxy)benzene:eugenol (8.02 g, 48.8 mmol), dimethyl acetal of 2-methylundecanal (33.7 g, 146 mmol), and KHSO4 (0.996 g, 7.31 mmol), the title compound (7.15 g, 21.6 mmol) was isolated in 44% yield as a pale yellow oil by distillation (bp>165°C, 3.3 Pa) (E / Z=60:40). [ka]

[0085] Starting with compound 6.2-methoxy-1-((2-methylundec-1-en-1-yl)oxy)-4-propylbenzene:dihydroeugenol (10 g, 60.2 mmol), dimethyl acetal of 2-methylundecanal (41.6 g, 181 mmol), and KHSO4 (1.23 g, 9.04 mmol), the title compound (9.07 g, 27.3 mmol) was isolated in 45% yield as a pale yellow oil by distillation (bp>165°C, 3.3 Pa) (E / Z=58:42). [ka]

[0086] Starting with compound 7.4-(4-((2-ethylhex-1-en-1-yl)oxy)phenyl)butan-2-one:4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) (10 g, 61 mmol), dimethyl acetal of 2-ethylhexanal (31.8 g, 182 mmol), and KHSO4 (0.998 g, 7.33 mmol), the title compound (2.26 g, 21.6 mmol) was isolated as a colorless liquid in 14% yield by distillation (bp 145-155°C, 6.7 Pa) (isomer ratio = 53:47). [ka]

[0087] General laboratory for compounds 8-12 Methoxymethyltriphenylphosphonium chloride (15.1 g, 44.1 mmol) and ketone (29.4 mmol) were added to 120 ml of toluene. Potassium t-butoxide (5.27 g, 47 mmol) was added to the stirred slurry in four portions at 15-minute intervals. The mixture was stirred for 4 to 24 hours until it turned crimson. This was then poured into 500 ml of water and extracted with SiO2 (3 × 250 mL). The organic phases were combined, dried over Na2SO4, filtered, and concentrated, during which triphenylphosphine oxide precipitated. The resulting methyl enol ether product was isolated either by direct distillation from the initial concentrate or by filtration, washing with diethyl ether to separate the precipitate, and then distillation. Subsequently, the isolated methyl enol ether (30-50 mmol) was combined with dihydroeugenol, eugenol, or 2-isopropyl-5-methylphenol (1 equivalent) and KHSO4 (25 mol%) in a round-bottom flask (25 mL) equipped with a distillation head and a nitrogen bubbler. The mixture was placed in an oil bath preheated to 180°C. The oil bath temperature was raised to 220°C over 10-15 minutes while distilling the liberated methanol from the reaction mixture. After 1 hour at 220°C, the mixture was removed from the oil bath and allowed to cool. The reaction mixture was placed under reduced pressure and heated to first distill off unreacted starting materials and volatile by-products. The remaining reaction mixture was further heated (in the oil bath up to 220°C) and the enol ether was distilled off. If necessary, the distilled enol ether was further purified by Kugellohr distillation or silica gel flash chromatography.

[0088] Compound 8.1-((2-ethyl-4,4-dimethylcyclohexylidene)methoxy)-2-methoxy-4-propylbenzene: The title compound was synthesized starting from 2-ethyl-4,4-dimethylcyclohexane-1-one. It was isolated from the intermediate methyl enol ether by short-pass distillation (bp 154-156°C, 2 Pa) as an amber oil in 35% yield (E / Z = 80:20). [ka]

[0089] Compound 9.2-Methoxy-1-((2-Pentylcyclopentylidene)methoxy)-4-propylbenzene: The title compound was synthesized starting from 2-Pentylcyclopentan-1-one. It was isolated from the intermediate methyl enol ether by short-pass distillation (bp 158-165°C, 2 Pa) as an amber oil in 27% yield (E / Z = 60:40). [ka]

[0090] Compound 10.2-Methoxy-1-((4-(tert-pentyl)cyclohexylidene)methoxy)-4-propylbenzene: The title compound was synthesized starting from 4-(tert-pentyl)cyclohexane-1-one. This was isolated from the crude reaction mixture by short-pass distillation (bp = 178-182°C, 2 Pa). This substance was subjected to Kugellohr distillation (185-200°C, 2 Pa), and the final product was obtained from the intermediate methyl enol ether as a colorless oil in 20% yield. [ka]

[0091] Compound 11.4-Allyl-2-methoxy-1-((4-(tert-pentyl)cyclohexylidene)methoxy)benzene: The title compound was synthesized starting from 4-(tert-pentyl)cyclohexane-1-one. This was isolated from the crude reaction mixture by short-pass distillation (bp = 177-180°C, 2 Pa). Silica gel flash chromatography (hexane / SiO, 99:1) was performed on this substance, and the final product was obtained in 6% yield as a colorless oil from the intermediate methyl enol ether. [ka]

[0092] Compound 12. 1-Isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene: The title compound was synthesized starting from 2-pentylcyclopentan-1-one. This was isolated from the crude reaction mixture by short-pass distillation (bp = 152-162°C, 2 Pa). This substance was subjected to silica gel flash chromatography (hexane) followed by Kugellool distillation (185°C, 2.6 Pa), and the final product was obtained from the intermediate methyl enol ether as a colorless oil in 16% yield (E / Z = 62:38). [ka]

[0093] Example 2 Synthesis of a compound according to formula (I) that releases a carbonyl compound of formula (II), which is an ester. General experimental section for compounds 13-22 A mixture of 2-bromoacetophenone (100 mmol), phenol (130 mmol), K2CO3 (150 mmol), and acetone (250 ml) was heated under reflux for 3-4 hours or stirred at room temperature for 1 day. The mixture was filtered through a Celite® bed, and the solution was concentrated. The resulting 2-phenoxyacetophenone was isolated by Kugellohr distillation or silica gel flash chromatography. The 2-phenoxyacetophenone was mixed with trimethyl orthoformate (7-10 equivalents), methanol (200 ml), and p-toluenesulfonic acid (0.02 equivalents), and the solution was heated at 70°C for 6-8 hours, followed by stirring at room temperature for 1 day to convert it to the corresponding dimethyl acetal. The mixture was monitored by gas chromatography to confirm the conversion to the acetal, although complete conversion was not achieved on several occasions. After adding solid Na2CO3 (0.06 equivalents), the mixture was concentrated under reduced pressure. The remaining residue was dissolved in diethyl ether and washed with water, saturated NH4Cl, and water. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting dimethyl acetal was used without further purification and combined with KHSO4 (0.01-0.02 equivalents) in a round-bottom flask equipped with a distillation head. The mixture was placed under reduced pressure (1.5 kPa) and then heated in an oil bath at 140°C for 1-2 hours. The mixture was removed from the oil bath and Na2CO3 (0.2 g) was added. The reaction mixture was dissolved in diethyl ether and washed with saturated Na2CO3. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting enol ether was purified by distillation or silica gel flash chromatography.

[0094] Compound 13.4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene: Starting with 4-allyl-1-(2,2-dimethoxy-2-phenylethoxy)-2-methoxybenzene (5.5 g, 16.7 mmol) and KHSO4 (0.17 mmol), the title compound (3.9 g, 15.1 mmol) was isolated in 79% yield as a pale yellow oil by Kugellohr distillation (195 °C, 2.6 Pa) (Z / E = 64:36). [ka]

[0095] Compound 14.2-Methoxy-1-((2-Methoxy-2-phenylvinyl)oxy)-4-propylbenzene: Starting with 1-(2,2-dimethoxy-2-phenylethoxy)-2-methoxy-4-propylbenzene (8 g, 24.2 mmol) and KHSO4 (0.24 mmol), the title compound (4.5 g, 15.1 mmol) was isolated in 62% yield as a yellow oil by Kugellohr distillation (180-190°C, 4.0 Pa) (Z / E=62:38). [ka]

[0096] Compound 15. Methyl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate: Starting with methyl 2-(2,2-dimethoxy-2-phenylethoxy)benzoate (13.5 g, 42.6 mmol) and KHSO4 (0.06 g, 0.44 mmol), the title compound (11.4 g, 40.0 mmol) was isolated in 94% yield as a yellow oil by Kugellohr distillation (150-155°C, 3.3 Pa) (Z / E = 64:36). [ka]

[0097] Compound 16. Methyl 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzoate: Starting with methyl 4-(3,3-dimethoxy-3-phenylpropyl)-3-methoxybenzoate (22.8 g, 65.8 mmol) and KHSO4 (0.09 g, 0.66 mmol), the title compound (17.2 g, 54.7 mmol) was isolated in 83% yield as a yellow oil by Kugellohr distillation (200-220°C, 2.0 Pa) (Z / E = 64:36). [ka]

[0098] Compound 17. 2 - Ethoxy - 1 - ((2 - methoxy - 2 - phenylvinyl)oxy)-4-(methoxymethyl)benzene: Starting from 1-(3,3 - dimethoxy - 3 - phenylpropyl)-2 - ethoxy - 4-(methoxymethyl)benzene (20.0 g, 57.8 mmol) and KHSO4 (0.08 g, 0.42 mmol), the title compound (10.4 g, 33.2 mmol) was isolated as a yellow oil in 57% yield by Kugelrohr distillation (195 °C, 3.3 Pa) (Z / E = 64:36).

Chem.

[0099] Compound 18. 2 - Ethoxy - 1 - ((2 - methoxy - 2 - phenylvinyl)oxy)-4 - methylbenzene: Starting from 1-(2,2 - dimethoxy - 2 - phenylethoxy)-2 - ethoxy - 4 - methylbenzene (15.8 g, 49.9 mmol) and KHSO4 (0.14 g, 1.0 mmol), the title compound (11.7 g, 41.1 mmol, 82% yield) was isolated as a pale amber oil by short - path distillation from the reaction flask (bp 168 - 170 °C, 1.5 Pa) after adding 0.22 g of Na2CO3 (Z / E = 51:49).

Chem.

[0100] Compound 19. 2 - Methoxy - 1 - ((2 - methoxy - 2-(p - tolyl)vinyl)oxy)-4 - propylbenzene: Starting from 1-(2,2 - dimethoxy - 2-(p - tolyl)ethoxy)-2 - methoxy - 4 - propylbenzene (17.3 g, 50.3 mmol) and KHSO4 (0.07 g, 0.51 mmol), the title compound (13.6 g, 43.4 mmol, 86% yield) was isolated as a pale yellow oil by Kugelrohr distillation of the reaction mixture (185 - 195 °C, 1.9 Pa) after adding 0.25 g of Na2CO3 (Z / E = 55:45). [ka]

[0101] Compound 20.2-Methoxy-1-((2-Methoxy-2-(4-Methoxyphenyl)vinyl)oxy)-4-propylbenzene:1-(2,2-dimethoxy-2-(4-Methoxyphenyl)ethoxy)-2-methoxy-4-propylbenzene (17.2 g, 47.7 mmol) and KHSO4 (0.13 g, 0.96 mmol) were used to isolate the title compound (11.8 g, 36 mmol, 75% yield) as a pale yellow oily substance by Kugellohr distillation (240°C, 2.4 Pa) of the reaction mixture after the addition of 0.2 g of Na2CO3 (Z / E = 54:46). [ka]

[0102] Compound 21. Cyclohexyl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate: Starting with cyclohexyl 2-(2,2-dimethoxy-2-phenylethoxy)benzoate (22.7 g, 59.1 mmol) and KHSO4 (0.20 g, 1.47 mmol), the title compound (4.31 g, 12.2 mmol) was isolated in 21% yield as a viscous amber oil by silica gel flash chromatography (hexane / siRNA 98:2) (Z / E=63:37). [ka]

[0103] Compound 22.1-Isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene: Starting with 2-(2,2-dimethoxy-2-phenylethoxy)-1-isopropyl-4-methylbenzene (26 g, 82.7 mmol) and KHSO4 (0.12 g, 0.88 mmol), the title compound (14.6 g, 51.8 mmol) was isolated in 63% yield as a pale amber oil by silica gel flash chromatography (hexane / siRNA 100:0 → 90:10) (Z / E = 63:37). [ka]

[0104] Compound 23. A mixture of (Z)-hex-3-en-1-yl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate:methyl 2-((2-methoxy-2-phenylvinyl)oxy)benzoate (Compound 15, 5.0 g, 17.6 mmol), (Z)-hex-3-en-1-ol (20.9 g, 209 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.48 g, 8.9 mmol) was added to a round-bottom flask (100 mL) equipped with a distillation head and a nitrogen bubbler. The flask was heated at 120 °C for 20 hours. The mixture was dissolved in diethyl ether and washed with water. The organic phase was dried over Na₂SO₄, filtered, and concentrated under reduced pressure. Excess alcohol was removed by short-pass distillation (bp 30-35 °C, 13.3 Pa). The residue was subjected to silica gel flash chromatography (hexane / SiO2 100:0 → 95:5) to obtain 4.16 g (11.8 mmol, 67% yield) of the title compound as a pale yellow oily substance (Z / E = 66:34). [ka]

[0105] Compound 24,3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde: A solution of morpholine (3.6 g, 41.4 mmol) and anhydrous THF (250 mL) was cooled to 5°C, and 31.9 mL of a 20 wt% toluene solution of DIBALH (38 mmol) was added dropwise. The mixture was stirred for 4 hours, and then methyl 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzoate (compound 16, 5 g, 15.9 mmol) dissolved in THF (10 mL) was added. After stirring for 30 minutes, 13.3 mL of DIBALH solution (15.9 mmol) was added dropwise over 10 minutes. The solution was stirred for a further 40 minutes, and then 75 mL of 1N HCl was slowly added. After stirring for 5 minutes, the reaction mixture was diluted with diethyl ether (500 mL), placed in a separatory funnel, and the phases were separated. The aqueous layer was extracted with ether, and the combined organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. To aid in purification, the remaining starting material was converted to a hexyl ester by heating a mixture of the crude product, hexanol (43.9 g, 429 mmol), and DBU (2.6 g, 17.2 mmol) at 120°C for 15 hours. The mixture was concentrated under reduced pressure, and the remaining residue was subjected to silica gel flash chromatography (hexane / CH2Cl2 100:0 → 0:100) followed by Kugelloor distillation to obtain 2.0 g (7.03 mmol, 44% yield) of the title compound as a viscous pale yellow oil (Z / E = 67:33). [ka]

[0106] Compound 25. 1-((2-Butoxy-2-phenylvinyl)oxy)-2-methoxy-4-propylbenzene: 1-(2,2-Dimethoxy-2-phenylethoxy)-2-methoxy-4-propylbenzene (10 g, 30.2 mmol) synthesized as described in the general experimental section of Compounds 13 to 22 was combined with butanol (4.48 g, 60.4 mmol) and KHSO4 (0.08 g, 0.60 mmol) in a round-bottom flask equipped with a distillation head. The mixture was heated for 3 hours using an oil bath at 120 °C while distilling the liberated MeOH from the flask. Then, the mixture was placed under reduced pressure (80 mbar) and heated at 140 °C for 2 hours while distilling the excess butanol from the flask. The mixture was removed from the oil bath and Na2CO3 (0.25 g) was added. The reaction mixture was dissolved in diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Flash column chromatography on silica gel (hexane / EtOAc 100:0 → 95:5) was performed on the residue to obtain 6.94 g (20.3 mmol, 67% yield) of the title compound as a pale yellow viscous oil (Z / E = 70:30). [Chemical Formula]

[0107] Compound 26. 2-Methoxy-1-((2-(octyloxy)-2-phenylvinyl)oxy)-4-propylbenzene: 1-(2,2-dimethoxy-2-phenylethoxy)-2-methoxy-4-propylbenzene (6 g, 18.1 mmol), synthesized as described in the general laboratory section for compounds 13-22, was combined with octanol (4.73 g, 36.3 mmol) and KHSO4 (0.1 g, 0.73 mmol) in a round-bottom flask equipped with a distillation head. The mixture was heated in an oil bath at 140°C for 2 hours, while distilling the liberated MeOH from the flask. The mixture was then placed under reduced pressure (3.5 kPa) and heated at 140-150°C for 3 hours, while distilling the excess octanol from the flask. The mixture was removed from the oil bath and Na2CO3 (0.25 g) was added. The reaction mixture was dissolved in diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel flash chromatography (hexane / siRNA 100:0 → 98:2) to obtain 5.29 g (13.3 mmol, 71% yield) of the title compound as a colorless, viscous oil (Z / E = 90:10). [ka]

[0108] Compound 27.1-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)-2-methoxy-4-propylbenzene: Compound 14 (8 g, 26.8 mmol) was combined with (Z)-3-hexen-1-ol (8.1 g, 80.9 mmol) and KHSO4 (0.23 g, 1.7 mmol) in a 35 mL round-bottom flask equipped with a distillation head. The mixture was heated in an oil bath at 140 °C for 1.5 hours, while distilling the liberated MeOH from the flask. The mixture was then placed under reduced pressure (8 kPa) and heated at 140-150 °C for 4 hours, while distilling the excess (Z)-3-hexen-1-ol from the flask. The mixture was removed from the oil bath and Na2CO3 (0.25 g) was added. The reaction mixture was filtered through a silica gel bed and concentrated under reduced pressure. KHSO4 (0.2 g) was added, and the mixture was further heated at 150°C (2 kPa) for 1.5 hours using a Kugellohr distillation apparatus. Silica gel flash chromatography (hexane / SiO2 100:0 → 97.5:2.5) was performed on the crude product to obtain 5.14 g (14.0 mmol, 52% yield) of the title compound as an amber-colored oil (Z / E = 71:29). [ka]

[0109] Compound 28.2-methoxy-1-((2-phenethoxy-2-phenylvinyl)oxy)-4-propylbenzene: Compound 14 (6.67 g, 22.4 mmol) was combined with 2-phenylethanol (5.47 g, 44.7 mmol) and KHSO4 (0.15 g, 1.1 mmol) in a 25 mL round-bottom flask equipped with a distillation head. The mixture was heated in an oil bath at 150 °C for 1.5 hours, while distilling the liberated MeOH from the flask. The mixture was then placed under reduced pressure (2 kPa) and heated at 150 °C for 4 hours, while distilling the excess 2-phenylethanol from the flask. Further KHSO4 (0.12 g, 0.88 mmol) was added, and the mixture was heated for a further 2 hours. The mixture was removed from the oil bath, and Na2CO3 (0.25 g) was added. The crude product was subjected to silica gel flash chromatography (hexane / siRNA 100:0 → 97.5:2.5) to obtain 6.62 g (17.0 mmol, 76% yield) of the title compound as a pale amber-colored viscous oil (Z / E = 70:30). [ka]

[0110] Compound 29. A mixture of 2-ethoxy-1-((2-ethoxy-2-phenylvinyl)oxy)-4-methylbenzene:2-(2-ethoxy-4-methylphenoxy)-1-phenylethane-1-one (10 g, 37 mmol; synthesized as described for compound 18) was mixed with triethyl orthoformate (7 equivalents), ethanol (200 ml), and p-toluenesulfonic acid (0.03 equivalents), and the solution was converted to diethyl acetal by heating at 80°C for 4 hours. Solid Na2CO3 (1.0 g) was added, and the mixture was concentrated under reduced pressure. The remaining residue was dissolved in diethyl ether and washed with water, saturated NH4Cl, and water. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting diethyl acetal was combined with KHSO4 (0.02 equivalents) in a round-bottom flask equipped with a distillation head. The mixture was placed under reduced pressure (1.5 kPa) and then heated in an oil bath at 140°C for 3 hours. The mixture was removed from the oil bath and Na2CO3 (0.2 g) was added. The reaction mixture was dissolved in diethyl ether and washed with saturated Na2CO3 and water. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting enol ether was purified by silica gel flash chromatography (hexane / CH2Cl290:10 → 60:40) to obtain 2.19 g (7.34 mmol, 20% yield) of the title compound as a pale yellow oil (Z / E = 62:38). [ka]

[0111] Compound 30, methyl 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzoate: Compound 16 (18.5 g, 58.9 mmol) was combined with 1-hexanol (24 g, 235.4 mmol) and KHSO4 (0.32 g, 2.35 mmol) in a round-bottom flask equipped with a distillation head. The mixture was heated in an oil bath at 140°C for 1 hour, while distilling the liberated MeOH from the flask. The mixture was placed under reduced pressure, gradually reduced from 50 kPa to 1.1 kPa, and heated at 150°C for 2 hours, while distilling the 1-hexanol from the flask. The mixture was removed from the oil bath and Na2CO3 (0.5 g) was added. The reaction mixture was dissolved in dichloromethane and washed with saturated Na2CO3 and water. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was subjected to silica gel flash chromatography (hexane / SiO2 100:0 → 91:9) to obtain 14.4 g (37.5 mmol, 64% yield) of the title compound as a pale amber oil (Z / E = 67:33). [ka]

[0112] A 20% by weight toluene solution (68 mL, 81.2 mmol) of compound 31 (4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxyphenyl)methanol:DIBALH was slowly added to a solution of compound 30 (7.8 g, 20.3 mmol) in anhydrous THF (250 mL) cooled to 0°C. The mixture was warmed to 25°C and stirred for 2 hours. After cooling again to 0°C, a 40% by weight aqueous solution of Rochelle salt (potassium sodium tartrate) was added over 15 minutes. The mixture was warmed to room temperature and diluted with diethyl ether (100 mL) and water (50 mL). The phases were separated, and the aqueous phase was extracted three times with diethyl ether. The organic phase was combined, dried over MgSO4, filtered, and concentrated under reduced pressure to obtain 6.9 g (19.4 mmol, 96% yield) of the title compound as a pale yellow, viscous oil (Z / E = 69:31). [ka]

[0113] Compound 32.4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde: A solution of compound 31 (6.0 g, 16.8 mmol) and pyridinium chlorochromate (5.44 g, 25.2 mmol) in 50 mL of dichloromethane was heated under reflux for 6 hours. After dilution with diethyl ether, the mixture was filtered through a layered bed of Celite® and silica gel. After removing the solvent under reduced pressure, the crude product was subjected to silica gel flash chromatography (hexane / siRNA 100:0 → 90:10) to obtain 2.81 g (7.9 mmol, 47% yield) of the title compound as a yellow oil (Z / E = 69:31). [ka]

[0114] Compound 33. Methyl 2-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)benzoate: Compound 15 (9.97 g, 35.1 mmol) was combined with (Z)-hex-3-en-1-ol (21 g, 210 mmol) and KHSO4 (0.24 g, 1.76 mmol) in a round-bottom flask equipped with a distillation head. The mixture was placed under reduced pressure (20 kPa) and heated for 3 hours using an oil bath at 140°C, while distilling the liberated MeOH and (Z)-hex-3-en-1-ol from the flask. Further KHSO4 (0.24 g, 1.76 mmol) was added, the pressure was reduced to 2 kPa, and the mixture was heated for a further 2 hours at 140°C. The reaction mixture was dissolved in ethyl acetate, filtered through a silica gel bed, and concentrated under reduced pressure. KHSO4 (0.24 g) was added, and the mixture was further heated at 150°C for 1 hour under reduced pressure (2 kPa) using a Kugellohr distillation apparatus. The crude product was subjected to silica gel flash chromatography (hexane / SiO2 100:0 → 95.5:4.5) to obtain 8.54 g (24.2 mmol, 69% yield) of the title compound as a pale yellow oil (Z / E = 68:32). [ka]

[0115] Compound 34. A mixture of (Z)-hex-3-en-1-yl 2-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)benzoate:methyl 2-((2-(((Z)-hex-3-en-1-yl)oxy)-2-phenylvinyl)oxy)benzoate (Compound 33, 5.0 g, 14.2 mmol), (Z)-hex-3-en-1-ol (26.4 g, 264 mmol), and DBU (1.34 g, 8.1 mmol) was added to a round-bottom flask (100 mL) equipped with a distillation head. The mixture was heated under reduced pressure (30 kPa) at 160 °C for 26 hours, while distilling MeOH and (Z)-hex-3-en-1-ol from the flask. The mixture was dissolved in ethyl acetate and washed with water. The organic phase was dried over MgSO4, filtered, and concentrated. The residue was subjected to silica gel flash chromatography (hexane / siRNA 90:10 → 85:15) to obtain 3.59 g (8.5 mmol, 60% yield) of the title compound as a colorless oil (Z / E = 69:31). [ka]

[0116] A 20% by weight toluene solution (108.8 mL, 129.8 mmol) of compound 35, (3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)phenyl)methanol:DIBALH, was slowly added to a solution of compound 16 (10.2 g, 32.4 mmol) in anhydrous THF (250 mL) cooled to 0°C. The mixture was warmed to 25°C and stirred for 2 hours. After cooling again to 0°C, a 40% by weight aqueous solution of Rochelle salt (potassium sodium tartrate) was added over 15 minutes. The mixture was warmed to room temperature and diluted with diethyl ether (100 mL) and water (50 mL). The phases were separated, and the aqueous phase was extracted three times with diethyl ether. The organic phases were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel flash chromatography (hexane / siRNA 100:0 → 70:30) to obtain 4.0 g (14.0 mmol, 43% yield) of the title compound as a pale yellow viscous oil (Z / E = 70:30). [ka]

[0117] Example 3 Headspace analysis from fabric softener applications containing the compound of formula (I) of the present invention A model liquid fabric softener was prepared by mixing 12.3% by weight of TEA-ester quat (Stepantex® VL90A), 0.4% by weight of a 10% calcium chloride aqueous solution, 0.04% by weight of Proxcel GXL, and 87.2% by weight of deionized water. Enol ether (0.075 mmol) was weighed into a vial and dissolved in 0.03 g of acetone. Liquid fabric softener (4.5 g) was added to the vial and the mixture was mixed by shaking by hand. A reference sample was prepared in the same manner using 0.075 mmol of each released volatile substance. The fabric softener sample was rinsed with deionized water and placed in a 3 L beaker, filling the beaker to a total volume of 1.5 L. Three 5 g cotton samples (approximately 12.5 × 12.5 cm, weighing 270 g / m²) were used. 2Product number 403 (Testfabrics, West Pittston, PA) was placed in a beaker and stirred by hand for 3 minutes. After standing for another 2 minutes, the sample was removed and excess water was squeezed out by hand. The cloth was hung to dry at room temperature for 1 or 3 days. Two of the three samples were placed in a thermostat-controlled (35°C) headspace sampling cell (approximately 160 mL in volume). An air sampling pump was used to pass a constant airflow (200 mL / min) through the sampling cell, and then through a cartridge containing 100 mg of Tenax®. To maintain a constant relative humidity of 75%, the air was drawn in by passing through an activated carbon plug before entering the sample cell and then through a saturated NaCl solution. For each sample, the headspace sample was collected as four 30-minute samples over a 2-hour period. The average headspace concentration of the released fragrance component for two samples over the 2-hour period is reported.

[0118] The cartridge was thermally desorbed using a Perkin Elmer TurboMatrix 650 thermal desorption unit mounted on an Agilent 6890 gas chromatograph equipped with an Agilent 5975C mass spectrometer and a Varian VF-1ms capillary column (30 m, 0.25 mm inner diameter, 0.25 μm membrane). The desorption unit parameters were: valve temperature 250°C, transfer line 240°C, purge time 1 minute, desorption temperature 240°C, desorption time 5 minutes, desorption flow rate 1 mL / min, trap -30°C to 240°C at 40°C / sec, trap holding time 5 minutes, outlet split 95 mL / min, and column flow rate 1 mL / min. The GC oven temperature profile was increased from 60°C (1 min) to 210°C at 20°C / min, then to 250°C (2 mins). Analysis of pipols revealed that the initial oven temperature was 52°C (2 mins). The amount of each fragrance volatile component recovered (reported as ng / 1L of air) was determined using external standard calibration for each chemical substance. At least five acetone solutions were prepared at concentrations of the analyte ranging from 0.05 g / L to 5 g / L. The solutions were injected into Tenax® cartridges (0.2 μL) and desorbed as described above. Each solution was analyzed three times. The calibration curve passed through the origin.

[0119] The dynamic headspace concentrations (ng / L) of the fragrance ingredients were obtained from hang-dried cotton treated with a fabric softener containing enol ether fragrance precursors, compared to their respective reference values ​​(average concentrations from headspace sampling over 2 hours).

[0120] [Table 1]

[0121] These data show that when applied to cotton fabrics for use as a fabric softener, the compound of formula (I) releases significantly more fragrance components (ketones and phenols) than the corresponding reference sample. This demonstrates that the compound of the present invention produces the desired sustained-release effect.

[0122] Example 4 Olfactory evaluation using a leave-on hair conditioner containing the compound of formula (I) of the present invention. The rinse-off hair conditioner for the model was manufactured with the following composition (by weight): Deionized water 95.50% Salcare SC 91 (Supplier: BASF) 1.00% Aculyn(TM) 46 (Supplier: Dow) 1.00% Wacker-Belsil® DMS 6038 (Supplier: Wacker) 0.50% Phenonip(TM) (Supplied by Clariant) 0.50% Mirasil® ADM-E (Supplier: Elkem) 1.5% A 25% enol ether solution in isopropyl myristate or a 25% enol ether solution in acetone was dispersed in a leave-on hair conditioner to obtain samples containing 0.15% or 0.25% by weight of the precursor, respectively. Reference samples containing expected equimolar levels of ketones and phenols were prepared in the same manner. The samples were allowed to acclimate at room temperature for 1 day. Hair samples (10 g) were rinsed with warm tap water (37°C) for 30 seconds, and then the hair was gently combed straight. One g of each hair conditioner sample was applied to the sample and massaged into the hair for complete dispersion. The samples were hung and dried at room temperature. The panel evaluated the odor intensity of these samples by olfaction after 6 and 24 hours. Panelists were asked to rate the perceived odor intensity on a scale ranging from 1 (not perceptible) to 7 (very strong). The data obtained from the panel evaluations are summarized in the table below.

[0123] [Table 2]

[0124] These data indicate that the compound of formula (I) produced a stronger odor intensity in the hair than the corresponding reference sample, both 6 and 24 hours after application from a leave-on hair conditioner. This demonstrates that the compound of the present invention produced the desired sustained-release effect.

[0125] Example 5 Olfactory evaluation using a rinse-off type hair conditioner containing the compound of formula (I) of the present invention. The rinse-off hair conditioner for the model was manufactured with the following composition (by weight): Deionized water 92.54% Chlorhexidine dihydrochloride 0.05% Natrosol® 250 H (Supplier: Hercules) 1.00% Dehyquart® C 4046 (Supplier: Cognis) 0.20% Mirasil® ADM-E (Supplier: Rhodia) 1.20% Genamin® KDM (Supplier: Clariant) 1.00% Crodamol® SS (Supplier: Croda) 0.50% Crodacol® C90 (Supplier: Croda) 3.01% Myristyl alcohol (supplier: Aldrich) 0.20% Nipagin® M (Supplier: Nipa) 0.30% A 25% enol ether solution in isopropyl myristate was dispersed at a concentration of 1% in rinse-off hair conditioner to obtain a conditioner containing 0.25% or 0.15% by weight of the precursor. Reference samples containing expected equimolar levels of ketones and phenols were prepared in the same manner. The samples were allowed to acclimate at room temperature for 1 day. Hair samples (10 g) were wet with warm tap water (37°C) and washed with unscented emulsion shampoo. Shampoo (1 mL) was applied with a syringe along the length of each hair sample. The samples were massaged with fingertips for 30 seconds to disperse the shampoo and create a good lather. These were rinsed with warm tap water for 30 seconds, and excess water was gently squeezed out. Rinse-off conditioner (1.0 g) was applied along the hair samples and gently massaged into the hair for 1 minute. The samples were then immersed in warm tap water in a 2 L beaker and moved up and down three times, then left and right three times. Next, the hair was gently detangled with fingertips and rinsed with tap water for 30 seconds. After gently squeezing out excess water, the sample was hung up to dry at room temperature. The panel evaluated the odor intensity of the sample by smell after 24 hours. Panelists were asked to rate the perceived odor intensity on a scale ranging from 1 (not perceptible) to 7 (very strong). The data obtained from the panel evaluation is summarized in the table below.

[0126] [Table 3]

[0127] These data indicate that the compound of formula (I) produced a stronger odor on the hair after application from a rinse-off hair conditioner than the corresponding reference sample. This demonstrates that the compound of the present invention produced the desired sustained-release effect.

[0128] Example 6 Olfactory evaluation using an antiperspirant / deodorant stick containing the compound of formula (I) of the present invention. The model deodorant was prepared using a commonly known method with the following composition (by weight): Dow Corning 345 Fluid 55.00% Lanette® 18 (Supplier: BASF) 21.00% Tegosoft® PBE (Supplier: Evonik) 2.00% Cutina® HR (Supplier: BASF) 1.00% Summit(R) AZP-908 (Supplier: SummitReheis) 20.00% A sample containing 0.15% by weight of an enol ether fragrance precursor was prepared by dispersing a 15:20 mixture of enol ether and isopropyl myristate in a molten antiperspirant composition. A reference sample containing expected equimolar levels of ketones and formate esters was prepared in the same manner. The molten samples were poured into deodorant stick molds and allowed to settle at room temperature for 1 day. 0.25 g of each sample was spread evenly on a 4.5 cm × 12 cm piece of blotting paper. The blotting paper was stored under ambient conditions for 24 hours. Panelists were asked to rate the perceived odor intensity on a scale ranging from 1 (not perceptible) to 7 (very strong). The data obtained from the panel evaluation are summarized in the table below.

[0129] [Table 4]

[0130] These data indicate that the compound of formula (I) produced a stronger odor intensity on the blotting paper after application from an antiperspirant stick than the corresponding reference sample. This demonstrates that the compound of the present invention produced the desired sustained-release effect.

Claims

1. From the precursor compound, a) Carbonyl compound of formula (II) 【Chemistry 1】 [In the formula, R ２ represents OR ２’ where R ２’ represents C １～６ alkyl group, phenethyl group or benzyl group, R １ is a phenyl group optionally substituted by one or two R １’ groups, where R １’ is simultaneously or independently a hydroxyl group, C １～３ alkyl group, or C １～３ alkoxy group, R ２ C １～3 When representing an alkyl group, R １ C １～4 Alkyl and / or C １～4 Phenyl or C which may be optionally substituted with one or more alkoxy groups. １～10 Represents an alkyl group; or R １ and R ２ This means that when these come together, C 1～8 C may be optionally substituted with one, two, or three alkyl groups. 5～6 Forms a cycloalkyl group ］； b) Formate ester of formula (III) 【Chemistry 2】 [In the formula, n represents an integer from 1 to 5; R ３ It simultaneously or independently represents at least one substituent of the aromatic ring, hydroxy, C １～６ C may be optionally substituted with an alkoxy or oxo group. １～６ Alkyl alkyl group; C １～３ C may be optionally substituted with an alkyl or methylene group. ４～７ Oxacycloalkyl or oxacycloalkenyl group; C ２～６ Alkenyl group; C １～６ Alkoxy group; or R ｂ It is an OCO group, and here, R ｂ C is a hydrogen atom. １～７ alkyl group, C ２～７ Alkenyl group, C ３～７ [A cycloalkyl group, a benzyl group, or a phenethyl group]; and c) Alcohol of formula (IV) 【Transformation 3】 [In the formula, R ３ [This has the same meaning as defined above]; A method for releasing a compound selected from the group consisting of, The precursor compound is a compound of formula (I). 【Chemistry 4】 [In the formula, n, R １ , R ２ , and R ３ This has the same meaning as defined above. A method comprising one or a mixture thereof of the stereoisomers of formula (I), wherein the release is produced by placing the precursor compound of formula (I) under conditions of room temperature, ambient air, and atmospheric pressure.

2. The method according to claim 1, wherein n is 1, 2, or 3.

3. R ３ However, hydroxy, C １～２ C may be optionally substituted with an alkoxy or oxo group. １～６ Alkyl alkyl group; C ２～６ Alkenyl group; C １～３ Alkoxy group; or R ｂ This represents the OCO group, where R ｂ C is a hydrogen atom. １～７ Alkyl, C ２～７ The method according to claim 1 or 2, wherein the group is an alkenyl or cyclohexyl group.

4. The method according to any one of claims 1 to 3, wherein at least one of the compounds of formulas (II), (III), and (IV) is a fragrance component.

5. The method according to any one of claims 1 to 4, wherein at least two of the compounds of formulas (II), (III), and (IV) are fragrance components.

6. A method for imparting, enhancing, improving, or modifying the olfactory properties of a fragrance composition, air surrounding a fragrance composition, a surface, or a fragranced article, comprising adding an effective amount of at least one compound of formula (I) as described in any one of claims 1 to 5 to a composition, air, or an article, or contacting or treating a surface with an effective amount of at least one compound of formula (I) as described in any one of claims 1 to 5.

7. A method for enhancing or extending the diffusion effect of the characteristic aroma of at least one carbonyl compound of formula (II), at least one formic acid ester of formula (III), and / or at least one alcohol of formula (IV) as described in any one of claims 1 to 5, in the air surrounding a surface or a fragrance composition, wherein the surface or the air is treated with at least one compound (I) as described in any one of claims 1 to 6, or with a composition or article containing at least one compound (I), under conditions that allow the release of at least one ketone of formula (II), at least one formic acid ester of formula (III), and / or at least one alcohol of formula (IV) over time.

8. i) At least one compound of formula (I) as defined in any one of claims 1 to 5; ii) At least one component selected from the group consisting of fragrance carriers and fragrance bases; and iii) At least one optional fragrance enhancer; A fragrance composition containing the following:

9. A fragranced consumer product containing at least one compound of formula (I) as defined in any one of claims 1 to 5 or a fragrance composition as defined in claim 8.

10. A fragrance-containing consumer product according to claim 9, which is a perfume, fabric care product, body care product, cosmetic, skin care product, air care product, or home care product.

11. Fragrance-containing consumer product according to claim 10, which is a fine perfume, splash or eau de perfume, cologne, shave or aftershave lotion, liquid or solid detergent, fabric softener, fabric refresher, ironing water, paper, bleach, carpet cleaner, curtain care product, shampoo, coloring preparation, color care product, hair styling product, dental care product, disinfectant, intimate care product, hair spray, hair conditioning product, vanishing cream, deodorant or antiperspirant, hair removal product, sunscreen or sunscreen, nail product, skin cleanser, cosmetic, fragrance-infused soap, shower or bath mousse, oil or gel, or foot / hand care product, hygiene product, deodorant, "ready-to-use" powder air freshener, mold remover, furniture care product, wipe, dish soap or hard surface cleaner, leather care product, or car care product.

12. A compound of formula (I) below which is one of the stereoisomers or a mixture thereof: 【Transformation 5】 [In the formula, R ２ OR ２’ This represents, and here, R ２’ C １～６ When representing an alkyl group, phenethyl group, or benzyl group, R １ is one or two R １’ A phenyl group which may be optionally substituted with a group, where R １’ The hydroxyl group, C, simultaneously or independently １～３ alkyl group, or C １～３ It is an alkoxy group, R ２ C １～3 When representing an alkyl group, R １ C １～4 Alkyl and / or C １～4 Phenyl or C which may be optionally substituted with one or more alkoxy groups. １～10 Represents an alkyl group; or R １ and R ２ This means that when these come together, C 1～8 C is substituted with one, two, or three alkyl groups. 5～6 Forms a cycloalkyl group; n represents an integer between 1 and 3; R ３ It simultaneously or independently represents at least one substituent of the aromatic ring, hydroxy, C １～６ C may be optionally substituted with an alkoxy or oxo group. １～６ Alkyl alkyl group; C ２～６ Alkenyl group; C １～６ Alkoxy group; or R ｂ It is an OCO group, and here, R ｂ C is a hydrogen atom. １～７ alkyl group, C ２～７ Alkenyl group, C ３～７ [A cycloalkyl group, a benzyl group, or a phenethyl group]; And, - R １ If it is methyl, then R ２ It is not methyl, - R １ If it is ethyl, then R ２ It is not ethyl, - 1,3-dimethoxy-2-((2-phenylprop-1-en-1-yl)oxy)benzene, 1-methyl-4-((-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl)oxy)benzene, 1-methyl-4-((-2-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)buta-1,3-dien-1-yl)oxy)benzene, and 1,2-dimethoxy-4-(1-(2-methoxyphenoxy)prop-1-en-2-yl)benzene are excluded. A compound of formula (I) provided that the following conditions are met.

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