Unsaturated ether fragrance precursor

Abstract

The use of a compound according to formula (I) as a fragrance precursor capable of releasing a fragrance having an aldehyde-like fragrance note is provided. Furthermore, fragrance compositions and consumer products containing the compound, as well as the compound itself, are also provided.

Description

[Technical Field] 【0001】 Technical field The present invention generally relates to fragrance precursors capable of releasing aromatic compounds. The present invention also relates to fragrance preparations and consumer products containing the precursors. The present invention further relates to methods for producing the fragrance precursors, fragrance preparations and consumer products, as well as to the use of the fragrance precursors and fragrance preparations in consumer products such as personal care products and household care products. [Background technology] 【0002】 background Fragranced consumer products, such as cleaning or laundry products containing fragrances, are well known in the art. However, it is known that fragrances can change through decomposition by interaction with air, or when incorporated into the base of certain consumer products where alkalinity, acidity, the presence of oxidizing agents such as hypochlorites, or other base components can lead to the chemical decomposition of the fragrance. In addition, volatile fragrances tend to dissipate over time. Furthermore, when used in cleaning or laundry products, the deposition of fragrance on the treated substrate is reduced by the washing and / or rinsing procedures. 【0003】 Nevertheless, consumers desire products that can be stored for extended periods while still retaining a certain fragrance impression. In particular, the effects of volatile components should be preserved. Furthermore, such products are desired to produce a long-lasting, pleasant fragrance that is slowly released over time from the treated substrate. 【0004】 To address these needs, fragrance precursors can be used, which are substances that are essentially odorless themselves but decompose under certain conditions to release aromatic molecules. 【0005】 Several classes of known precursors exist that release aromatic molecules upon activation by hydrolysis, temperature changes, oxygen, light, and enzymes. For example, WO2012085287 reports a group of precursors that can release fragrances by spontaneous air oxidation. WO2007143873 describes another group of precursors that can be cleaved by hydrolysis. 【0006】 Generally, precursors exhibit different stabilities and release aromatic molecules under different conditions. For example, there is a need to provide additional precursor systems to improve the effect of fragrance on dried fabric after several days. Therefore, it is desirable to provide new or improved systems that can release fragrance over a long period and provide a long-lasting fragrance release. [Overview of the project] 【0007】 overview According to a first aspect of the present invention, the use of a compound as a fragrance precursor that can release a fragrance over a long period of time and provide a long-lasting release of the fragrance is provided. According to a second aspect of the present invention, a compound as a precursor is provided. 【0008】 A third aspect of the present invention provides a method for releasing a fragrance. A fourth aspect of the present invention provides a method for producing the fragrance precursor, fragrance preparation, and consumer product. 【0009】 According to a fifth aspect of the present invention, fragrance preparations and consumer products containing the compound are provided. According to a sixth aspect of the present invention, the use of the fragrance precursor and fragrance preparation in consumer products such as fabric care products, personal care products and household care products is provided. 【0010】 Details, examples, and preferences provided in connection with any particular one or more aspects of the described aspects of the Invention will be further described herein and will apply equally to all aspects of the Invention. Unless otherwise indicated herein or unless the context clearly contradicts it, any combination of embodiments, examples, and preferences described herein, in all possible variations thereof, is encompassed by the Invention. [Modes for carrying out the invention] 【0011】 Detailed explanation This invention is based on the surprising finding that simple homoallyl esters, carbonates, carbamates, and sulfonates can serve as fragrance precursors capable of releasing fragrances. These fragrance precursors provide a delayed release of fragrance over a longer period than using fragrance compounds directly. 【0012】 Therefore, in this specification, formula (I): [ka] The compound is offered for use as a fragrance precursor. During the ceremony, X is selected from C and S (=O); R1 is linear or branched C1-C 11 Selected from the group consisting of alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-naphthyl)-eth-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and dialkylamine-NR5R6 (where R5 and R6 are independently selected from the group consisting of C1-C4 alkyl groups); R2 is a linear C7-C chain with a terminal CC double bond.10 Alkyl and linear C7-C 10 Selected from a group consisting of alkenils; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me. 【0013】 For example, the use of a compound of formula (I) as a fragrance precursor is provided, where the compound is of formula (Ia): [ka] It is a compound of, During the ceremony, R1 is linear or branched C1-C 11 Selected from the group consisting of alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-naphthyl)-eth-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and dialkylamine-NR5R6 (where R5 and R6 are independently selected from the group consisting of C1-C4 alkyl groups); R2 is a linear C7-C chain with a terminal CC double bond. 10 Alkyl and linear C7-C 10 Selected from a group consisting of alkenils; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me. 【0014】 Compounds of formula (Ia) correspond to compounds of formula (I) where X is C. Compounds of formula (Ia) include homoallyl esters, carbonates, and carbamates. 【0015】 For example, use as a fragrance precursor of a compound of formula (I) is provided, wherein the compound is a compound of formula (Ib) [Chemical formula] wherein in which R1 is a linear or branched C1-C 11 alkyl; methoxy; ethoxy; phenyl having up to 5 substituents independently selected from methyl, ethyl, methoxy, ethoxy; naphthyl having up to 4 substituents independently selected from methyl, ethyl, methoxy, ethoxy; 1-naphthyl-methyl having up to 2 substituents independently selected from methyl, ethyl, methoxy, ethoxy; 1-(2-naphthyl)-ethan-1-yl having up to 2 substituents independently selected from methyl, ethyl, methoxy, ethoxy; dialkylamine -NR5R6 (R5 and R6 are independently selected from the group consisting of C1-C4 alkyl); R2 is a linear C7-C having a terminal C═C double bond 10 alkyl and linear C7-C 10 alkenyl; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me. 【0016】 The compound of formula (Ib) corresponds to the compound of formula (I) where X is S(═O). The compound of formula (Ib) includes sulfonates. For example, the compound of formula (Ib) is a mesylate where R1 is methyl, or a tosylate where R1 is tolyl and R2-R4 are as defined above. 【0017】 The compounds of formula (Ia) and (Ib) are subgroups of the compounds of formula (I). Thus, unless otherwise stated, the description regarding the compounds of formula (I) applies to the compounds of formula (Ia) and (Ib). <> 【0018】 The compound according to formula (I) may have one CC double bond, which may have either an E- or Z- configuration, or, unless otherwise specified, an E- / Z- mixture. The compound of formula (I) has one stereocenter and exists in two enantiomer forms. The compound of formula (I) may be enantiomerically pure, concentrated, or a racemic mixture. 【0019】 For example, C1~C 11 Alkyl compounds can be selected from the group consisting of methyl, ethyl, linear or branched propyl (n-propyl, iso-propyl, etc.), butyl (n-butyl, iso-butyl, sec-butyl, tert-butyl, etc.), pentyl, hexyl, heptyl, octyl, nonyl, decyl, and undecyl. For example, linear C7~C 10 Alkyls can be selected from the group consisting of linear heptyl, octyl, nonyl, and decyl groups. For example, a linear C7-C chain having terminal CC double bonds. 10 The alkenil can be selected from the group consisting of hepta-6-en-1-yl, octa-7-en-1-yl, nona-8-en-1-yl, and deca-9-en-1-yl. 【0020】 For example, the use of a compound according to formula (I) as a fragrance precursor capable of releasing a fragrance having an aldehyde-like note is provided. Generally, the release of aromatic molecules is activated by external triggers such as hydrolysis, temperature changes, oxygen, light and / or enzyme action. 【0021】 Some of the compounds according to formula (I) are known from different contexts. For example, document WO2013060818A1 describes a process for producing a group of compounds having the relevant structure that are suitable intermediates or precursors for the production of other chemical compounds. The term “intermediate or precursor” means that the compound is not used as is, but is further converted into a different compound by subsequent preparation steps. This document does not mention fragrance precursors that can release fragrances with aldehyde notes upon activation. 【0022】 Typically, compounds according to formula (I) are odorless or have a weak odor when freshly prepared, and can release fragrances having, for example, aldehyde-like fragrance notes. However, in some embodiments of the present invention, compounds according to formula (I) may have a characteristic odor. 【0023】 The use of the compound according to formula (I) makes it possible to provide aldehyde-like fragrance notes over a long period of time, and to provide a long-lasting release of aldehyde-like fragrance notes. 【0024】 Aldehyde-like fragrance notes typically provide an olfactory impression that can be described with other words such as metallic, sharp, or piercing (which is a more physical impression or association). Other aldehyde-related terms include "fatty aldehydic" and "aldehydic green." In olfactory terminology, "aldehyde-like" is not strictly related to the chemical characteristics of aldehydes in their molecular structure. Therefore, a typical aldehyde-like odor has become an olfactory standard independent of the chemical characteristics of aldehydes in their molecular structure. 【0025】 For example, the use of a compound according to formula (I) as a fragrance precursor is provided, where the compound is selected from the group consisting of: tetradeca-1,13-dien-4-yl acetate, tetradeca-1-en-4-yl acetate, trideca-1-en-4-yl acetate, tetradeca-1-en-4-yl benzoate, trideca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-yl benzoate, tetradeca-1,13-dien-4-yl 2-naphthate, trideca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-(naphthalene-1-yl) acetate, trideca-1-en-4-yl 2-(naphthalene-1-yl) acetate, tetradeca-1,13-di En-4-yl 2-(naphthalene-1-yl) acetate, trideca-1-en-4-yl 2-methyl undecanoate, tetradeca-1-en-4-yl 2-methyl undecanoate, tetradeca-1-en-4-yl dimethylcarbamate, methyltetradeca-1-en-4-yl carbonate, pentadeca-3-en-6-yl acetate, pentadeca-3-en-6-yl benzoate, trideca-1-en-4-yl 3,4,5-trimethoxybenzoate, tetradeca-1-en-4-yl 3,4,5-trimethoxybenzoate, undeca-1-en-4-yl benzoate, dodeca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-ylmethanesulfonate, and tetradeca-1,13-dien-4-yl 4-methylbenzenesulfonate. 【0026】 According to one aspect of the present invention, the use of a compound according to formula (I) as a fragrance precursor is provided, where the compound is an ester, and where R1 is linear or branched C1-C 11Selected from the group consisting of alkyl; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthylmethyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and 1-(2-naphthyl)-ethyl-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and R2, R3, and R4 have the same meanings as previously defined. 【0027】 The compound according to formula (I) above releases a fragrance compound when the precursor compound is exposed to ambient air for an extended period (e.g., several days, such as 2 to 7 days, or even longer). 【0028】 Exposure of the precursor compound to the ambient air means exposure to molecular oxygen, which can cause cleavage of the compound according to formula (I) and release of fragrance. The concentration of oxygen in the air is sufficient to cleave the compound according to formula (I), thereby allowing the cleavage product to be detected in the ambient air, for example, by olfactory analysis of a headspace sample. 【0029】 Compounds according to formula (I) are highly stable when their exposure to ambient air is limited or prevented, i.e., when stored in neat form in a suitable container protected from air and light, or when stored in a suitable solvent, such as ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, isopropyl myristate, triethyl citrate, diethyl phthalate, triacetin and / or diacetin, or when incorporated into consumer products such as detergents, shampoos and fabric conditioners. Therefore, compounds according to formula (I) can find applications in a wide range of consumer products where long-term and defined release of aromatic compounds is desired. 【0030】 Therefore, in a further aspect of the present invention, a method is provided for releasing a fragrance from a compound according to formula (I), wherein the compound is exposed to an environmental inducer. For example, the environmental inducer is ambient air or another oxygen source. 【0031】 In some embodiments, to limit or prevent premature cleavage of the compound according to formula (I), stabilizing compounds, such as alpha-tocopherol, EDTA, ascorbic acid, BHT, and Tinoguard® TT, can be added to the compound according to formula (I) in amounts of, for example, 0.01 to 1% by weight. In particular, stabilizing compounds can be used to enhance the stability of neat compounds according to formula (I). 【0032】 Compounds according to formula (I) may be used alone or in combination with known odor molecules selected from a wide range of natural products and currently available synthetic molecules, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocyclic compounds and heterocyclic compounds, and / or in combination with one or more components or excipients conventionally used in combination with odor molecules in fragrance compositions, such as carrier materials, and other auxiliary agents commonly used in the art. For example, such known odor molecules are described in "Perfume and Flavor Chemicals," edited by S. Arctander, Volumes I and II (Allured Publishing Corporation, Carol Stream, USA, 2003), and include fragrance compounds and essential oils of natural or synthetic origin. 【0033】 In a further respect, the compound according to formula (I) may be used in combination with other fragrance precursors (further compounds according to formula (I) or precursors having different chemical structures). The combination of precursors can release a perfume accord. 【0034】 In a further aspect, a fragrance composition comprising at least one compound according to formula (I) is provided. For example, the fragrance composition further comprises one or more known odor molecule molecules and / or one or more components or excipients conventionally used in combination with odor molecules in fragrance compositions. 【0035】 Compounds according to formula (I) can be included in a wide variety of amounts in a fragrance composition, depending on the effect the perfumer wishes to achieve. For example, the compound may be used in amounts of 0.01 to 80% by weight, or 0.1 to 50% by weight, or 1% to 20% by weight. These values ​​are shown merely as examples, and other amounts may be applied. 【0036】 As used herein, "carrier material" means a material that is substantially neutral with respect to odor substances, that is, a material that does not significantly alter the sensory perception properties of odor substances. 【0037】 The term “adjuvants” refers to components that may be used in a fragrance composition for reasons not particularly related to the olfactory performance of the composition. For example, adjuvants may be components that act to assist in the processing of one or more fragrance components or a composition containing such components, or they may improve the handling or storage of fragrance components or compositions containing them. They may also be components that provide additional benefits, such as imparting color or texture. They may also be components that impart lightfastness or chemical stability to one or more components contained in the fragrance composition. A detailed description of the properties and types of adjuvants commonly used in fragrance compositions containing adjuvants cannot be exhaustive, but it should be noted that such components are well known to those skilled in the art. 【0038】 As used herein, “fragrance composition” means any composition comprising a compound according to formula (I) and a diluent conventionally used in combination with a base material, such as diethyl phthalate (DEP), dipropylene glycol (DPG), isopropyl myristate (IPM), pentane-1,2-diol, triethyl citrate (TEC), and an odorant such as alcohol (e.g., ethanol). Optionally, the composition may also contain an antioxidant adjuvant. The antioxidant may be selected from Tinogard® TT (BASF), Tinogard® Q (BASF), tocopherol (including its isomers CAS 59-02-9; 364-49-8; 18920-62-2; 121854-78-2), 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT, CAS 128-37-0) and related phenols, hydroquinone (CAS 121-31-9). 【0039】 The following non-restrictive list includes examples of known odor molecules that may be combined with compounds of formula (I) in fragrance compositions: Essential oils and extracts, such as castorium, costus root oil, oakmoss absolute, geranium oil, tree moss absolute, fruit oils such as basil oil, bergamot oil and mandarin oil, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, jasmine oil, rose oil, sandalwood oil, wormwood oil, lavender oil, and / or ylang-ylang oil; • Alcohols, for example, cinnamol ((E)-3-phenylpropane-2-en-1-ol); cis-3-hexenol ((Z)-hexa-3-en-1-ol); citronellol (3,7-dimethylocta-6-en-1-ol); dihydromyrcenol (2,6-dimethylocta-7-en-2-ol); Ebanol (registered trademark) ((E)-3-methyl-5-(2,2,3-trimethylcyclopene) (T-3-en-1-yl)penta-4-en-2-ol); eugenol (4-allyl-2-methoxyphenol); ethyllinalool ((E)-3,7-dimethylnonano-1,6-dien-3-ol); farnesol ((2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol); geraniol ((E)-3,7-dimethylocta-2,6-dien-1-ol); Super Muguet (registered trademark) ((E)-6-ethyl-3-methylocta-6-en-1-ol); Linalool (3,7-dimethylocta-1,6-dien-3-ol); Menthol (2-isopropyl-5-methylcyclohexanol); Nerol (3,7-dimethyl-2,6-octadien-1-ol); Phenylethyl alcohol (2-phenylethanol); Rhodinol (trademark) (3,7-dimethylocta-6-en-1-ol); Sandalore (registered trademark) (3- Methyl-5-(2,2,3-trimethylcyclopenta-3-en-1-yl)pentan-2-ol); terpineol (2-(4-methylcyclohexa-3-en-1-yl)propane-2-ol) or Timberol® (1-(2,2,6-trimethylcyclohexyl)hexane-3-ol); 2,4,7-trimethylocta-2,6-dien-1-ol, and / or [1-methyl-2(5-methylhexa-4-en-2-yl)cyclopropyl]methanol; Aldehydes and ketones, e.g., anisaldehyde (4-methoxybenzaldehyde); alpha-amyl cinnamic aldehyde (2-benzylidene heptanal); Georgywood (trademark) (1-(1,2,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone); hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal); Iso E Super(registered trademark) (1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-yl)ethanone); Isoraldeine(registered trademark) ((E)-3-methyl-4-(2,6,6-trimethylcyclohexa-2-en-1-yl)buta-3-en-2-one); Hedione(registered trademark) (methyl 3-oxo-2-pentylcyclopentane acetate); Nympheal(trademark) (3-(4-isobutyl-2-methylphenyl)propanal); Mahonial(trademark) (5,9-dimethyl-9-hydroxydecene-4-al); Maltol; Methylcedyl ketone; Methyl ionone; Verbenone; and / or Vanillin; Ethers and acetals, e.g., Ambrox® (3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran); geranyl methyl ether ((2E)-1-methoxy-3,7-dimethylocta-2,6-diene); rose oxide (4-methyl-2-(2-methylpropa-1-en-1-yl)tetrahydro-2H-pyran); and / or Spirambrene® (2',2',3,7,7-pentamethylspiro[bicyclo[4.1.0]heptane-2,5'-[1,3]dioxane]); • Esters and lactones, e.g., benzyl acetate; cedyl acetate ((1S,6R,8aR)-1,4,4,6-tetramethyloctahydro-1H-5,8a-methanoazulene-6-yl acetate); γ-decalactone (6-pentyltetrahydro-2H-pyran-2-one); Helvetolide® (2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropylpropionate); γ-undecalactone (5-heptyloxolan-2-one); and / or vetiveryl acetate ((4,8-dimethyl-2-propane-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulene-6-yl) acetate); • Macrocyclic compounds, e.g., ambretlide ((Z)-oxacycloheptadeca-10-en-2-one); ethylene brassilate (1,4-dioxacycloheptadecane-5,17-dione); and / or exaltlide (registered trademark) (16-oxacyclohexadecane-1-one); and Heterocyclic compounds, such as isobutylquinoline (2-isobutylquinoline). 【0040】 In a further embodiment, a consumer product is provided comprising a compound according to at least one formula (I) and a consumer product base. 【0041】 For example, consumer products according to the present invention are selected from the fields of detergents and cleaning agents, hygiene products or care products, preferably body care and hair care, cosmetics and household products, and preferably include fragrance extracts, eau de parfum, eau de toilette, aftershave lotion, eau de cologne, pre-shave products, spray cologne, scented refreshing wipes, acidic, alkaline or neutral detergents, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pretreatment agents, fabric softeners, laundry sheets, laundry soap, and laundry tablets. The group consists of solid dish soap, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, aftershave creams and lotions, sunscreens and lotions, hair care products (in liquid or solid form), dry shampoos, deodorants, antiperspirants, decorative cosmetic products, candles, lamp oils, incense, insecticides, repellents, and fuels. 【0042】 Consumer products are selected from, for example, fine fragrances, personal care products (body care products, hair care products, cosmetic products), fabric care products, home care products, and air care products. As used herein, “consumer product base” means a composition intended for use as a consumer product to perform a specific action such as cleansing, softening, and care. 【0043】 Personal care products to which the compound of formula (I) may be added include, for example, all kinds of body care products. Of particular interest are hair care products, such as shampoos, conditioners, and hairsprays, as well as skin care products such as lotions or creams. Furthermore, the compound of formula (I) may be added to soaps, bath gels, and shower gels, as well as deodorants. The compound of formula (I) may be added to cosmetic products. 【0044】 Household care products to which the compound of formula (I) may be added include all kinds of detergents, window cleaners, hard surface cleaners, multi-purpose cleaners, and furniture polishes. Preferably, the product is a liquid, for example, a fabric detergent or conditioner composition. 【0045】 For example, the compound of formula (I) can also act as a fragrance precursor in consumer products that further contain enzymes. 【0046】 Compounds according to formula (I) can be used in a wide range of scented consumer products, for example, in high-quality and functional perfumes in any field (perfumes, air care products, household products, laundry products, body care products, and cosmetics). The compound can be used in a wide variety of amounts depending on the specific article and the properties and amounts of other odor-causing components. The proportion of formula (I) is typically 0.0001 to 5% by weight of the article. In one embodiment, the compound of formula (I) may be used in fabric softeners in amounts of 0.001 to 0.3% by weight (e.g., 0.01 to 0.1% (including 0.05% by weight)). In another embodiment, the compound of formula (I) may be used not only in high-quality perfumes but also in consumer products such as shampoos, fabric softeners, or fabric detergents in amounts of 0.001 to 30% by weight (e.g., up to about 10% by weight, or up to 20% by weight), more preferably 0.01 to 5% by weight. However, these values ​​are given as examples only. This is because an experienced perfumer may also be able to achieve the desired effect or create a new harmony through lower or higher concentrations. 【0047】 In one embodiment, a consumer product is provided that contains an acceptable amount of a compound of formula (I). For example, a flavored article may contain, based on the total weight of the article, a compound of formula (I) in amounts ranging from 0.000001% by weight to 90% by weight (including 0.00001%, 0.0001%, 0.001%, 0.01%, 0.05%, 0.1%, 0.5%, 1%, 5%, 8%, 10%, 15%, 20%, 25%, 30%, 50%, 60%, and 65%) of a compound of formula (I). 【0048】 The compound of formula (I) may be used in a consumer product base simply by directly mixing the compound of the present invention or a fragrance composition containing the compound of formula (I) with the consumer product base, or, in an earlier step, it may be captured with a capture material (e.g., polymers, capsules, microcapsules and nanocapsules, liposomes, film-forming agents, absorbents such as carbon or zeolites, cyclic oligosaccharides, and mixtures thereof) and then mixed with the consumer product base. The consumer product base may further contain capture substances that can release other aromatic compounds. 【0049】 Accordingly, the present invention also provides a method for manufacturing a consumer product, the method comprising incorporating the compound of formula (I) by directly mixing the compound of formula (I) into a consumer product base, or by mixing a fragrance composition containing the compound of formula (I) and then mixing this with a consumer product base using the prior art and methods. Through the addition of an acceptable amount of the compound of the present invention as described above, the scent note of the consumer product to be applied will be improved, imparted, enhanced, or modified. 【0050】 Therefore, in another embodiment, the present invention further provides a method for imparting, enhancing, improving or modifying the hedonic properties of a fragrance composition or consumer product, the method comprising adding at least one compound of formula (I) to the composition or consumer product. Some compounds based on formula (I) are known from various applications; however, most of the compounds are novel. 【0051】 Therefore, the present invention is based on formula (I): [ka] Provides compounds by During the ceremony, X is selected from C and S (=O); R1 is linear or branched C1-C 11 Selected from the group consisting of alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-naphthyl)-eth-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and dialkylamine-NR5R6 (where R5 and R6 are independently selected from the group consisting of C1-C4 alkyl groups); R2 is a linear C7-C chain with a terminal CC double bond. 10 Alkyl and linear C7-C 10 Selected from a group consisting of alkenils; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me, However, the compound is not tetradeca-1-en-4-yl acetate, trideca-1-en-4-yl acetate, tetradeca-1,13-diene-4-yl acetate, undeca-1-en-4-yl benzoate, undeca-1-en-4-yl pivalate, or undeca-1-en-4-yl acetate, methylundeca-1-en-4-yl carbonate, dodeca-1,11-diene-4-yl acetate, or dodeca-1-en-4-yl acetate. 【0052】 For example, equation (Ia): [ka] A compound represented by the following is provided: During the ceremony, R1 is linear or branched C1-C 11 Selected from the group consisting of alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-naphthyl)-eth-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and dialkylamine-NR5R6 (where R5 and R6 are independently selected from the group consisting of C1-C4 alkyl groups); R2 is a linear C7-C chain with a terminal CC double bond. 10 Alkyl and linear C7-C 10 Selected from a group consisting of alkenils; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me, However, the compound is not tetradeca-1-en-4-yl acetate, trideca-1-en-4-yl acetate, tetradeca-1,13-diene-4-yl acetate, undeca-1-en-4-yl benzoate, undeca-1-en-4-yl pivalate, or undeca-1-en-4-yl acetate, methylundeca-1-en-4-yl carbonate, dodeca-1,11-diene-4-yl acetate, or dodeca-1-en-4-yl acetate. 【0053】 For example, a compound according to formula (Ia) defined above is provided, Here, R2 is a linear C9-C with a terminal CC double bond. 10 Alkyl and linear C7-C 10Selected from the group consisting of alkenyls. 【0054】 For example, equation (Ib): [ka] Compounds are provided by, During the ceremony, R1 is linear or branched C1-C 11 Selected from the group consisting of alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-naphthyl)-eth-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; and dialkylamine-NR5R6 (where R5 and R6 are independently selected from the group consisting of C1-C4 alkyl groups); R2 is a linear C7-C chain with a terminal CC double bond. 10 Alkyl and linear C7-C 10 Selected from a group consisting of alkenils; R3 is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R4 is selected from the group consisting of H and Me. 【0055】 The compound according to formula (I) may have one CC double bond, which may have either an E- or Z- configuration, or, unless otherwise specified, an E- / Z- mixture. The compound according to formula (I) has one stereocenter and exists in two enantiomer forms. The compound according to formula (I) may be enantiomerically pure, concentrated, or a racemic mixture. 【0056】 For example, compounds of formula (I) include tetradeca-1-en-4-ylbenzoate, trideca-1-en-4-ylbenzoate, tetradeca-1,13-dien-4-ylbenzoate, tetradeca-1,13-dien-4-yl 2-naphthoate, trideca-1-en-4-yl 2-naphthoate, tetradeca-1-en-4-yl 2-(naphthalene-1-yl)acetate, trideca-1-en-4-yl 2-(naphthalene-1-yl)acetate, tetradeca-1,13-dien-4-yl 2-(naphthalene-1-yl)acetate, trideca-1-en-4-yl 2-methylundecanoate, tetradeca-1-en-4-yl 2-methylundecanoate, tetradeca-1,13-dien-4-yl 2-(naphthalene-1-yl)acetate, trinaphthoate, tetradeca-1,13-dien-4-yl 2-naphthoate, tetradeca-1,13-dien-4-yl 2-naphthoate, tetradeca-1,13-dien-4-yl 2-naphthoate, tetradeca-1,13 Selected from the group consisting of tradedeca-1-en-4-yl 2-methylundecanoate, tetradeca-1-en-4-yldimethylcarbamate, methyltetradeca-1-en-4-yl carbonate, (Z)-pentadeca-3-en-6-yl acetate, (Z)-pentadeca-3-en-6-yl benzoate, trideca-1-en-4-yl 3,4,5-trimethoxybenzoate, tetradeca-1-en-4-yl 3,4,5-trimethoxybenzoate, dodeca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-ylmethanesulfonate, and tetradeca-1,13-dien-4-yl 4-methylbenzenesulfonate. 【0057】 Compounds according to formula (I) may be produced by esterification of an alcohol with an acyl chloride or sulfonyl chloride using methods known in the art. 【0058】 Alternatively, the compound according to formula (I) may be obtained by the reaction of an aldehyde with allyl magnesium chloride, followed by the acylation of the resulting alcohol with acyl anhydride or acyl chloride. For example, the compound according to formula (I) may be prepared by a method in which allyl Grignard addition and esterification are carried out in the same reaction vessel without isolation or purification of intermediates. Grignard addition forms a magnesium alkoxide, which further reacts with acyl anhydride or acyl chloride, or sulfonyl chloride. In the one-pot reaction described, no base is required to quench the Grignard reaction during acylation or between the two steps. 【0059】 The present invention will now be further described with reference to the following non-limiting examples. These examples are for illustrative purposes only, and it will be understood that variations and modifications can be made by those skilled in the art. 【0060】 example General: All reactions were carried out under argon, using solvents and reagents from commercial suppliers without further purification. Solvents for extraction and chromatography were industrial grade and used without further purification. Flash chromatography was performed using Tsingdao Haiyang Chemical silica gel (200-300 mesh) and Santai Technologies silica flash columns. Unless otherwise stated, a heptane:MTBE mixture was used as the eluent. NMR spectra were recorded using an AW 400 MHz Bruker spectrometer. 1 The chemical shifts for the 1H NMR spectra are reported in δ (ppm) relative to the residual proton signal of the deuterated solvent; the coupling constants are expressed in Hertz (Hz). 13¹³C NMR spectra were referenced to the carbon signal of the deuterated solvent. The following abbreviations were used: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, dd = double doublet, bs = broad singlet. GC / MS spectral data were obtained from Agilent 6890 N and MSD 5975 using HP-5 MS columns, 30 m, 0.25 mm, and 0.25 μm. High-resolution mass spectra were determined using Thermo Fisher Scientific LTQ FT Ultra (ESI-MS) and Waters Micromass GCT Premier (EI-MS). 【0061】 Example 1: Tetradeca-1,13-diene-4-ylacetate Example 1a: Tetradeca-1,13-diene-4-ol A solution of undeca-10-enal (42.1 g, 50 mL, 250 mmol) in tetrahydrofuran (THF) (250 mL) was slowly treated at 0°C with a solution of allyl magnesium chloride in THF (138 mL, 2 M, 276 mmol). The resulting mixture was stirred overnight at 25°C. The mixture was poured onto an ice-cold NH4Cl solution, extracted twice with methyl tert-butyl ether (MTBE), washed with brine, dried over MgSO4, and evaporated. The crude product was purified by fractionate distillation through a 5 cm Vigreux column to obtain tetradeca-1,13-dien-4-ol (38.8 g, 68% yield, 92% purity) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.91 - 5.75 (m, 2H), 5.19 - 5.10 (m, 2H), 5.06 - 4.89 (m, 2H), 3.71 - 3.59 (m, 1H), 2.36 - 2.27 (m, 1H), 2.21 - 2.10 (m, 1H), 2.09 - 2.00 (m, 2H), 1.71 (d, J = 3.9 Hz, 1H), 1.52 - 1.24 (m, 14H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 139.2, 134.9, 118.0, 114.1, 70.7, 41.9, 36.8, 33.8, 29.6, 29.5, 29.4, 29.1, 28.9, 25.7. 【0062】 Example 1b: Tetradeca-1,13-diene-4-ylacetate A solution of tetradeca-1,13-diene-4-ol (5.26 g, 25 mmol) in toluene (100 mL) was treated with pyridine (5.05 mL, 62.5 mmol) and DMAP (N,N-dimethylpyridine-4-amine) (92 mg, 0.75 mmol), and then, while cooling in a water bath, was treated dropwise with a solution of acetyl chloride in toluene (25 mL) (1.96 mL, 27.5 mmol). The resulting mixture was stirred at ambient temperature for 3 hours, then poured over ice-cooled 2N HCl, extracted with MTBE, washed with brine, dried over MgSO4, and evaporated. The crude product was purified by Kugellohr distillation to obtain tetradeca-1,13-diene-4-yl acetate (5.38 g, 20 mmol, 92% purity, 78% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.89 - 5.69 (m, 2H), 5.12 - 4.87 (m, 5H), 2.38 - 2.21 (m, 2H), 2.11 - 1.98 (m, 5H), 1.62 - 1.49 (m, 2H), 1.43 - 1.22 (m, 12H).13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 170.7, 139.1, 133.8, 117.5, 114.1, 73.3, 38.6, 33.8, 33.6, 29.4, 29.4, 29.4, 29.1, 28.9, 25.3, 21.2. MS (EI, 70eV): 211 (2, [M +* - allyl]), 192 (0), 135 (3), 95 (5), 81 (5), 67 (5), 55 (7), 43 (100). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, citrus. 【0063】 Example 2: Tetradeca-1-en-4-ylacetate A solution of allyl magnesium chloride in THF (16.2 mL, 1.7 molar concentration, 1.1 equivalents, 27.5 mmol) was cooled to 0°C, and then slowly treated with a solution of undecanal in THF (5 mL) (4.26 g, 5.16 mL, 1 equivalent, 25.0 mmol). The resulting mixture was stirred at 0°C for 2 hours. The mixture was then slowly treated with acetic anhydride (3.06 g, 2.83 mL, 1.2 equivalents, 30.0 mmol) at 0–15°C and stirred at 25°C for 1 hour. The mixture was then poured over 2N HCl (50 mL), extracted with MTBE (2 × 25 mL), and washed with saturated Na₂CO₃ solution (25 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered, and concentrated to obtain a crude product, which was purified by Kugelloor distillation (oven at 175°C / 0.097 mbar) to yield tetradeca-1-en-4-yl acetate (5.57 g, 21 mmol, 84% yield, 96% purity) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.76 (tdd, J = 7.2, 10.1, 17.1 Hz, 1H), 5.15 - 5.03 (m, 2H), 4.92 (quin, J = 6.2 Hz, 1H), 2.37 - 2.26 (m, 2H), 2.04 (s, 3H), 1.60 - 1.50 (m, 2H), 1.39 - 1.20 (m, 16H), 0.93 - 0.86 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 170.8, 133.8, 117.5, 73.3, 38.6, 33.6, 31.9, 29.6, 29.6, 29.5, 29.4, 29.3, 25.3, 22.7, 21.2, 14.1. MS (EI, 70eV): 213 (1, [M +* - Allyl]), 194 (1), 153 (2), 111 (5), 97 (12), 83 (7), 67 (5), 55 (7), 43 (100), 41 (12). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, citrus, mandarin leaf. 【0064】 Example 3: Trideca-1-en-4-ylacetate The compound was prepared using decanal (instead of undecanal) according to the procedure described in Example 2, yielding trideca-1-en-4-yl acetate (62% yield, 89% purity) as a colorless liquid. 1H NMR (500 MHz, CDCl3, 298 K) δ (ppm) = 5.77 (tdd, J = 7.1, 10.1, 17.1 Hz, 1H), 5.13 - 5.04 (m, 2H), 4.93 (quin, J = 6.3 Hz, 1H), 2.38 - 2.27 (m, 2H), 2.05 (s, 3H), 1.59 - 1.52 (m, 2H), 1.35 - 1.22 (m, 14H), 0.90 (t, J = 7.0 Hz, 3H). 13 C NMR (126 MHz, CDCl3, 298 K) δ (ppm) = 170.8, 133.8, 117.5, 73.4, 38.7, 33.6, 31.9, 29.5, 29.5, 29.3, 25.3, 22.7, 21.2, 14.1. MS (EI, 70eV): 199 (1, [M +* - Allyl]), 180 (1), 157 (1), 139 (3), 97 (5), 83 (9), 67 (4), 55 (6), 43 (100). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, citrus. 【0065】 Example 4: Tetradeca-1-en-4-ylbenzoate The compound was prepared using benzoyl chloride (instead of acetic anhydride) according to the procedure described in Example 2, yielding tetradeca-1-en-4-ylbenzoate (69% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.10 - 8.04 (m, 2H), 7.61 - 7.54 (m, 1H), 7.49 - 7.43 (m, 2H), 5.85 (tdd, J = 7.1, 10.1, 17.1 Hz, 1H), 5.24 - 5.05 (m, 3H), 2.52 - 2.43 (m, 2H), 1.79 - 1.63 (m, 2H), 1.47 - 1.20 (m, 16H), 0.95 - 0.86 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.2, 133.7, 132.7, 130.8, 129.5, 128.3, 117.7, 74.1, 38.7, 33.7, 31.9, 29.6, 29.6, 29.5, 29.3, 25.3, 22.7, 14.1. MS (EI, 70eV): 316 (1, [M +* ]), 287 (1), 194 (2), 123 (2), 105 (100), 77 (14), 41 (6). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, citrus, mandarin leaf. 【0066】 Example 5: Trideca-1-en-4-ylbenzoate The compound was prepared using decanal (instead of undecanal) and benzoyl chloride (instead of acetic anhydride) according to the procedure described in Example 2, yielding trideca-1-en-4-ylbenzoate (52% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.07 (dd, J = 1.3, 8.4 Hz, 2H), 7.60 - 7.54 (m, 1H), 7.49 - 7.43 (m, 2H), 5.86 (tdd, J = 7.2, 10.1, 17.1 Hz, 1H), 5.24 - 5.16 (m, 1H), 5.16 - 5.05 (m, 2H), 2.51 - 2.44 (m, 2H), 1.76 - 1.64 (m, 2H), 1.46 - 1.21 (m, 14H), 0.93 - 0.86 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.2, 133.7, 132.7, 130.8, 129.5, 128.3, 117.7, 74.1, 38.7, 33.7, 31.9, 29.5, 29.5, 29.3, 25.3, 22.7, 14.1. MS (EI, 70eV): 302 (1, [M +* ]), 261 (1), 180 (1), 123 (1), 105 (100), 77 (15), 41 (7). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, green, citrus, mandarin leaf. 【0067】 Example 6: Tetradeca-1,13-diene-4-ylbenzoate The compound was prepared using benzoyl chloride (in place of acetyl chloride) according to the procedure described in Example 1b, yielding tetradeca-1,13-diene-4-ylbenzoate (77% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.10 - 8.04 (m, 2H), 7.61 - 7.54 (m, 1H), 7.50 - 7.41 (m, 2H), 5.92 - 5.76 (m, 2H), 5.24 - 4.91 (m, 5H), 2.50 - 2.44 (m, 2H), 2.10 - 2.00 (m, 2H), 1.83 - 1.62 (m, 2H), 1.52 - 1.24 (m, 12H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.2, 139.2, 133.7, 132.7, 130.7, 129.5, 128.3, 117.7, 114.1, 74.1, 38.7, 33.8, 33.7, 29.5, 29.5, 29.4, 29.1, 28.9, 25.3. MS (EI, 70eV): 314 (1, [M +* ]), 273 (1), 192 (1), 123 (2), 105 (100), 77 (13), 41 (7). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, citrus. 【0068】 Example 7: Tetradeca-1,13-diene-4-yl-2-naphthoate The compound was prepared using 2-naphthoyl chloride (in place of acetyl chloride) according to the procedure described in Example 1b, yielding tetradeca-1,13-diene-4-ylbenzoate (62% yield) as a yellow liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.63 (d, J = 0.7 Hz, 1H), 8.09 (dd, J = 1.7, 8.6 Hz, 1H), 7.99 (d, J = 7.8 Hz, 1H), 7.95 - 7.86 (m, 2H), 7.65 - 7.53 (m, 2H), 5.99 - 5.72 (m, 2H), 5.34 - 5.21 (m, 1H), 5.16 (qd, J = 1.6, 17.0 Hz, 1H), 5.10 (td, J = 1.0, 10.3 Hz, 1H), 5.00 (qd, J = 1.8, 17.1 Hz, 1H), 4.94 (tdd, J = 1.2, 2.2, 10.1 Hz, 1H), 2.57 - 2.48 (m, 2H), 2.09 - 1.98 (m, 2H), 1.86 - 1.67 (m, 2H), 1.52 - 1.22 (m, 12H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.4, 139.2, 135.5, 133.8, 132.5, 130.9, 129.3, 128.1, 128.1, 128.0, 127.7, 126.6, 125.3, 117.8, 114.1, 74.2, 38.8, 33.8, 33.7, 29.4, 29.1, 28.9, 25.4. MS (EI, 70eV): 364 (1, +* ]), 323 (1), 209 (1), 172 (28), 155 (100), 127 (29), 55 (9), 41 (10). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, green, metallic. 【0069】 Example 8: Trideca-1-en-4-il2-naftart Example 8a: Trideca-1-en-4-ol The compound was prepared using decanal (instead of undeca-10-enal) according to the procedure described in Example 1a, yielding trideca-1-en-4-ol (95% yield) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.85 (dddd, J = 6.4, 7.9, 9.6, 17.6 Hz, 1H), 5.22 - 5.11 (m, 2H), 3.72 - 3.62 (m, 1H), 2.33 (tddd, J = 1.3, 4.2, 6.5, 13.9 Hz, 1H), 2.22 - 2.09 (m, 1H), 1.62 (br d, J = 11.5 Hz, 1H), 1.54 - 1.23 (m, 16H), 0.95 - 0.85 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 134.9, 118.0, 70.7, 41.9, 36.8, 31.9, 29.7, 29.6, 29.6, 29.3, 25.7, 22.7, 14.1. 【0070】 Example 8b: Trideca-1-en-4-il2-naftart The compound was prepared using 2-naphthoyl chloride (in place of acetyl chloride) and trideca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding trideca-1-en-4-yl 2-naphthoate (75% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.62 (d, J = 0.7 Hz, 1H), 8.09 (dd, J = 1.6, 8.7 Hz, 1H), 8.03 - 7.96 (m, 1H), 7.91 (d, J = 8.6 Hz, 2H), 7.65 - 7.52 (m, 2H), 5.90 (tdd, J = 7.0, 10.2, 17.1 Hz, 1H), 5.27 (qd, J = 5.7, 7.5 Hz, 1H), 5.16 (qd, J = 1.6, 17.0 Hz, 1H), 5.10 (tdd, J = 1.0, 2.0, 10.0 Hz, 1H), 2.57 - 2.48 (m, 2H), 1.86 - 1.67 (m, 2H), 1.52 - 1.20 (m, 14H), 0.94 - 0.84 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.4, 135.5, 133.8, 132.5, 130.9, 129.3, 128.1, 128.1, 128.0, 127.7, 126.6, 125.3, 117.8, 74.2, 38.8, 33.7, 31.9, 29.5, 29.5, 29.3, 25.4, 22.7, 14.1. +* ]), 337 (1), 311 (1), 172 (26), 155 (100), 127 (31), 55 (5), 41 (9). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, green, metallic, mandarin leaf. 【0071】 Example 9: Tetradeca-1-en-4-il-2-naphthoart Example 9a: Tetradeca-1-en-4-ol The compound was prepared using undecanal (instead of undeca-10-enal) according to the procedure described in Example 1a, yielding tetradeca-1-en-4-ol (96% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.92 - 5.78 (m, 1H), 5.22 - 5.09 (m, 2H), 3.66 (br s, 1H), 2.32 (tddd, J = 1.3, 4.2, 6.6, 13.9 Hz, 1H), 2.21 - 2.10 (m, 1H), 1.64 (s, 1H), 1.54 - 1.22 (m, 18H), 0.95 - 0.83 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 134.9, 118.0, 70.7, 41.9, 36.8, 31.9, 29.7, 29.6, 29.6, 29.3, 25.7, 25.6, 22.7, 14.1. 【0072】 Example 9b: Tetradeca-1-en-4-yl2-naphthoart The compound was prepared using 2-naphthoyl chloride (in place of acetyl chloride) and tetradeca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding tetradeca-1-en-4-yl 2-naphthoate (66% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.62 (d, J = 0.7 Hz, 1H), 8.09 (dd, J = 1.7, 8.6 Hz, 1H), 8.03 - 7.96 (m, 1H), 7.91 (d, J = 8.6 Hz, 2H), 7.66 - 7.53 (m, 2H), 5.90 (tdd, J = 7.1, 10.2, 17.2 Hz, 1H), 5.27 (qd, J = 5.9, 7.4 Hz, 1H), 5.20 - 5.06 (m, 2H), 2.57 - 2.49 (m, 2H), 1.86 - 1.67 (m, 2H), 1.52 - 1.19 (m, 16H), 0.94 - 0.84 (m, 3H). 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.4, 135.5, 133.8, 132.5, 130.9, 129.3, 128.1, 128.1, 128.0, 127.7, 126.6, 125.3, 117.8, 77.2, 74.2, 38.8, 33.7, 31.9, 29.6, 29.6, 29.5, 29.3, 25.4, 22.7, 14.1. +* ]), 325 (1), 194 (2), 172 (27), 155 (100), 127 (29), 55 (5), 41 (9). Odor description (1% solution in EtOH on paper blotter, 24h): Green, metallic, aldehyde-like. 【0073】 Example 10: Tetradeca-1-en-4-yl-2-(naphthalene-1-yl)acetate The compound was prepared using 2-(naphthalene-1-yl)acetyl chloride (in place of acetyl chloride) and tetradeca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding tetradeca-1-en-4-yl 2-naphthoate (76% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.08 - 8.00 (m, 1H), 7.92 - 7.86 (m, 1H), 7.85 - 7.79 (m, 1H), 7.58 - 7.48 (m, 2H), 7.48 - 7.41 (m, 2H), 5.73 - 5.60 (m, 1H), 5.03 - 4.90 (m, 3H), 4.08 (s, 2H), 2.32 - 2.24 (m, 2H), 1.56 - 1.46 (m, 2H), 1.38 - 1.09 (m, 16H), 0.97 - 0.89 (m, 3H). 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 171.3, 133.8, 133.6, 132.1, 130.9, 128.7, 128.0, 127.9, 126.2, 125.7, 125.4, 124.0, 117.5, 73.9, 39.6, 38.6, 33.5, 31.9, 29.6, 29.5, 29.5, 29.4, 29.4, 25.1, 22.7, 14.1. +* ]), 339 (1), 186 (19), 169 (3), 141 (100), 115 (13). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, green, metallic, fatty, citrus leaf, hot iron. 【0074】 Example 11: Trideca-1-en-4-yl2-(naphthalene-1-yl)acetate The compound was prepared using 2-(naphthalene-1-yl)acetyl chloride (in place of acetyl chloride) and trideca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding trideca-1-en-4-yl 2-(naphthalene-1-yl)acetate (67% yield) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.08 - 8.01 (m, 1H), 7.92 - 7.87 (m, 1H), 7.85 - 7.78 (m, 1H), 7.58 - 7.49 (m, 2H), 7.48 - 7.42 (m, 2H), 5.74 - 5.61 (m, 1H), 5.05 - 4.90 (m, 3H), 4.08 (s, 2H), 2.35 - 2.22 (m, 2H), 1.57 - 1.45 (m, 2H), 1.40 - 1.10 (m, 14H), 0.93 (t, J = 7.0 Hz, 3H). 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 171.3, 133.8, 133.6, 132.1, 130.9, 128.7, 128.0, 127.9, 126.2, 125.7, 125.4, 124.0, 117.6, 73.9, 39.6, 38.6, 33.6, 31.9, 29.5, 29.5, 29.4, 29.3, 25.1, 22.7, 14.2. +* ]), 325 (1), 186 (16), 169 (3), 141 (100), 115 (14), 41 (14). Odor description (1% solution in EtOH on paper blotter, 24h): Green, citrus, aldehyde-like, metallic, fatty, citrus leaf, hot iron. 【0075】 Example 12: Tetradeca-1,13-diene-4-yl-2-(naphthalene-1-yl)acetate The compound was prepared using 2-(naphthalene-1-yl)acetyl chloride (in place of acetyl chloride) according to the procedure described in Example 1b, yielding tetradeca-1,13-dien-4-yl 2-(naphthalene-1-yl)acetate (37% yield) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.07 - 8.01 (m, 1H), 7.92 - 7.86 (m, 1H), 7.81 (dd, J = 2.8, 6.5 Hz, 1H), 7.58 - 7.48 (m, 2H), 7.48 - 7.42 (m, 2H), 5.85 (tdd, J = 6.6, 10.3, 17.1 Hz, 1H), 5.73 - 5.60 (m, 1H), 5.08 - 4.89 (m, 5H), 4.08 (s, 2H), 2.32 - 2.23 (m, 2H), 2.12 - 2.01 (m, 2H), 1.56 - 1.44 (m, 2H), 1.44 - 1.08 (m, 12H). 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 171.3, 139.2, 133.6, 132.1, 130.9, 128.7, 128.0, 127.9, 126.2, 125.7, 125.4, 124.0, 117.6, 114.1, 73.9, 39.6, 38.6, 33.8, 33.5, 29.4, 29.3, 29.1, 28.9, 25.1.M +* ]), 337 (2), 186 (19), 169 (2), 141 (100), 115 (14), 55 (16). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, metallic, citrus leaf, hot iron, green. 【0076】 Example 13: Trideca-1-en-4-yl-2-methylundecanoate Example 13a: 2-Methylundecanoyl chloride A mixture of 2-methylundecanoic acid (6.92 g, 1 equivalent, 34.5 mmol) and DMF (N,N-dimethylformamide) (37.9 mg, 40.1 μL, 0.015 equivalents, 518 μmol) was treated dropwise with thionyl chloride (14.4 g, 8.78 mL, 3.5 equivalents, 121 mmol) at 10°C and stirred at room temperature for 2 hours. The resulting mixture was directly purified by Kugellohr distillation to yield 2-methylundecanoyl chloride (6.35 g, 33 mmol, 98% purity, 95% yield) as a colorless liquid. 1 H NMR (500 MHz, CDCl3, 298 K) δ (ppm) = 2.88 (sxt, J = 6.8 Hz, 1H), 1.88 - 1.76 (m, 1H), 1.58 - 1.48 (m, 1H), 1.41 - 1.21 (m, 17H), 0.95 - 0.86 (m, 3H). 13C NMR (126 MHz, CDCl3, 298 K) δ (ppm) = 177.8, 51.5, 33.4, 31.9, 29.5, 29.4, 29.4, 29.3, 26.7, 22.7, 17.0, 14.1. 【0077】 Example 13b: Trideca-1-en-4-yl-2-methylundecanoate The compound was prepared using 2-methylundecanoyl chloride (in place of acetyl chloride) and trideca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding trideca-1-en-4-yl 2-methylundecanoate (68% yield) as a colorless liquid (a 1:1 mixture of diastereomers). 1 H NMR (500 MHz, CDCl3, 298 K, 1:1 mixture of diastereomers) δ (ppm) = 5.82 - 5.70 (m, 1H), 5.11 - 5.04 (m, 2H), 4.97 - 4.90 (m, 1H), 2.46 - 2.37 (m, 1H), 2.37 - 2.26 (m, 2H), 1.71 - 1.61 (m, 1H), 1.60 - 1.51 (m, 2H), 1.44 - 1.36 (m, 1H), 1.36 - 1.21 (m, 28H), 1.17 - 1.12 (m, 3H), 0.93 - 0.86 (m, 6H). 13 ¹³C NMR (126 MHz, CDCl₃, 298 K, 1:1 mixture of diastereomers) δ (ppm) = 176.6, 176.5, 133.9, 117.4, 117.4, 72.8, 72.7, 40.0, 39.9, 38.8, 38.8, 33.9, 33.6, 31.9, 29.6, 29.6, 29.5, 29.4, 27.3, 25.3, 25.3, 22.7, 17.3, 17.3, 14.1. MS (EI, 70eV): 380 (1, [M +*]), 323 (1), 309 (1), 295 (1), 281 (1), 267 (1), 254 (1), 225 (1), 201 (4), 183 (84), 180 (11), 155 (18), 113 (13), 99 (31), 85 (58), 71 (57), 57 (100), 43 (64). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, metallic, balsamic, incense, citrus, green. 【0078】 Example 14: Tetradeca-1-en-4-yl-2-methylundecanoate The compound was prepared using 2-methylundecanoyl chloride (in place of acetyl chloride) and tetradeca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding tetradeca-1-en-4-yl 2-methylundecanoate (64% yield) as a colorless liquid (a 1:1 mixture of diastereomers). 1 H NMR (500 MHz, CDCl3, 298 K, 1:1 mixture of diastereomers) δ (ppm) = 5.82 - 5.71 (m, 1H), 5.12 - 5.03 (m, 2H), 4.97 - 4.89 (m, 1H), 2.47 - 2.37 (m, 1H), 2.37 - 2.26 (m, 2H), 1.71 - 1.63 (m, 1H), 1.59 - 1.51 (m, 2H), 1.44 - 1.37 (m, 1H), 1.36 - 1.22 (m, 30H), 1.17 - 1.12 (m, 3H), 0.92 - 0.87 (m, 6H). 13¹³C NMR (126 MHz, CDCl₃, 298 K, 1:1 mixture of diastereomers) δ (ppm) = 176.6, 176.5, 133.9, 117.5, 117.5, 72.8, 72.7, 40.0, 39.9, 38.8, 38.8, 33.9, 33.6, 31.9, 29.6, 29.6, 29.6, 29.6, 29.5, 29.4, 27.3, 25.3, 25.3, 22.7, 17.4, 17.3, 14.1. MS (EI, 70eV): 394 (1, [M +* ]), 194 (11), 183 (98), 155 (17), 113 (13), 99 (31), 85 (60), 71 (58), 57 (100), 43 (66). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, metallic, balsamic, fragrant, citrusy, green. 【0079】 Example 15: Tetradeca-1-en-4-yldimethylcarbamate A flask containing NaH (55% dispersion in mineral oil) (0.24 g, 5.5 mmol) and toluene (2.5 mL) was slowly treated at 25°C with a solution of tetradeca-1-en-4-ol in toluene (2.5 mL) (1.1 g, 5.0 mmol). The resulting mixture was heated and refluxed for 1 hour. The resulting mixture was cooled to 0°C and slowly treated with a solution of dimethylcarbamate chloride in toluene (1.5 mL) (0.55 mL, 0.65 g, 6.0 mmol). The mixture was stirred at 25°C for 16 hours. The mixture was then poured into water, extracted twice with MTBE, washed with brine, and dried over MgSO4. The resulting crude material was purified by Kugellohr distillation to obtain tetradeca-1-en-4-yldimethylcarbamate (1.32 g, 90% purity, 84% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.79 (tdd, J = 7.1, 10.1, 17.1 Hz, 1H), 5.12 - 5.01 (m, 2H), 4.79 (quin, J = 6.1 Hz, 1H), 2.91 (br s, 6H), 2.37 - 2.29 (m, 2H), 1.61 - 1.51 (m, 2H), 1.39 - 1.22 (m, 16H), 0.93 - 0.86 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 156.5, 134.2, 117.2, 74.3, 38.9, 36.3 (br), 35.7 (br), 33.8, 31.9, 29.6, 29.3, 25.3, 22.7, 14.1. MS (EI, 70eV): 283 (1, [M +* ]), 242 (1), 194 (3), 90 (16), 72 (100), 41 (13). Odor description (1% solution in EtOH on paper blotter, 24h): Powdery, aldehyde-like, fatty, metallic, citrusy, green. 【0080】 Example 16: Methyltetradeca-1-en-4-yl carbonate The compound was prepared using methyl chloroformate (instead of acetyl chloride) and tetradeca-1-en-4-ol (instead of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding methyltetradeca-1-en-4-yl carbonate (87% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.79 (tdd, J = 7.1, 10.2, 17.2 Hz, 1H), 5.15 - 5.06 (m, 2H), 4.80 - 4.70 (m, 1H), 3.78 (s, 3H), 2.41 - 2.34 (m, 2H), 1.70 - 1.52 (m, 2H), 1.42 - 1.21 (m, 16H), 0.93 - 0.86 (m, 3H). 13 MS (EI, 70eV): 194 (4, [M +* - HOC(O)OCH3]), 153 (4), 111 (28), 97 (100), 83 (85), 77 (14). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, metallic, green, marine. 【0081】 Example 17: (Z)-pentadeca-3-en-6-ilacetato Example 17a: (Z)-pentadeca-3-en-6-ol A flask was packed with magnesium (495 mg, 1 equivalent, 20.4 mmol) and 0.1 g of bromononane, and Grignard formation was initiated using a heating gun. A solution of 1-bromononane (4.22 g, 1 equivalent, 20.4 mmol) in THF (20 mL) was added dropwise over 25 minutes. After the addition, the reaction mixture was heated to 50°C for 30 minutes until all the magnesium turning was dissolved. The Grignard reagent was cooled to -20°C and treated dropwise over 10 minutes with a solution of freshly distilled (Z)-hexa-3-enal (2.00 g, 1 equivalent, 20.4 mmol) in THF (10 mL). After the addition, the condenser was removed, and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into a saturated NH4Cl solution, extracted twice with MTBE, washed with water and brine until neutral, dried over MgSO4, filtered, and concentrated. The resulting material was purified by chromatography on silica gel (elution with MTBE in heptane) and subsequent Kugelloor distillation to yield (Z)-pentadeca-3-en-6-ol (1.4 g, 98% purity, 30% yield) as a colorless oil. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.64 - 5.55 (m, 1H), 5.46- 5.35 (m, 1H), 3.69 - 3.56 (m, 1H), 2.27 - 2.20 (m, 2H), 2.15 - 2.04 (m, 2H), 1.56 (br s, 1H), 1.53 - 1.41 (m, 2H), 1.38 - 1.23 (m, 14H), 0.99 (t, J = 7.5 Hz, 3H), 0.94 - 0.87 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 135.1, 124.6, 71.5, 36.9, 35.2, 31.9, 29.7, 29.6, 29.6, 29.3, 25.8, 22.7, 20.7, 14.3, 14.1. 【0082】 Example 17b: (Z)-pentadeca-3-en-6-ilacetato The compound was prepared using (Z)-pentadeca-3-en-6-ol (instead of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding (Z)-pentadeca-3-en-6-yl acetate (67% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.55 - 5.46 (m, 1H), 5.38 - 5.27 (m, 1H), 4.89 (quin, J = 6.2 Hz, 1H), 2.37 - 2.22 (m, 2H), 2.11 - 2.01 (m, 4H), 1.59 - 1.51 (m, 2H), 1.37 - 1.23 (m, 14H), 0.98 (t, J = 7.6 Hz, 3H), 0.93 - 0.87 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 170.8, 134.3, 123.6, 74.0, 33.6, 31.9, 31.8, 29.5, 29.5, 29.3, 25.4, 22.7, 21.3, 20.6, 14.2, 14.1. MS (EI, 70eV): 208 (7, [M +* - HOC(O)CH3]), 199 (1), 95 (10), 82 (24), 43 (100). Odor description (1% solution in EtOH on paper blotter, 24h): Green, fatty, watery, metallic, aldehyde-like, mandarin. 【0083】 Example 18: (Z)-pentadeca-3-en-6-ylbenzoate The compound was prepared using benzoyl chloride (in place of acetyl chloride) and (Z)-pentadeca-3-en-6-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding (Z)-pentadeca-3-en-6-ylbenzoate (41% yield) as a colorless liquid. 11H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.10 - 8.03 (m, 2H), 7.62 - 7.53 (m, 1H), 7.50 - 7.43 (m, 2H), 5.55 - 5.36 (m, 2H), 5.21 - 5.11 (m, 1H), 2.55 - 2.36 (m, 2H), 2.15 - 1.95 (m, 2H), 1.79 - 1.62 (m, 2H), 1.49 - 1.19 (m, 14H), 0.96 (t, J = 7.6 Hz, 3H), 0.92 - 0.86 (m, 3H). 13 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.3, 134.4, 132.7, 130.8, 129.5, 129.5, 128.3, 123.5, 74.7, 33.7, 31.9, 31.9, 29.5, 29.3, 25.4, 22.7, 20.7, 14.1, 14.1. MS (EI, 70eV): 261 (1), 208 (7), 105 (100), 77 (16). Description in ethanol 1% solution on paper blotter for 24 h: green, metallic, aldehyde-like, mandarin. 【0084】 Example 19: Tridec-1-en-4-yl 3,4,5-trimethoxybenzoate The compound was prepared according to the procedure described in Example 1b using 3,4,5-trimethoxybenzoyl chloride (instead of acetyl chloride) and tridec-1-en-4-ol (instead of tetradeca-1,13-dien-4-ol), yielding tridec-1-en-4-yl 3,4,5-trimethoxybenzoate (63% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 7.31 (s, 2H), 5.84 (tdd, J = 7.1, 10.2, 17.2 Hz, 1H), 5.21 - 5.05 (m, 3H), 3.92 (s, 6H), 3.91 (s, 3H), 2.50 - 2.42 (m, 2H), 1.81 - 1.61 (m, 2H), 1.49 - 1.21 (m, 14H), 0.92 - 0.84 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 165.8, 152.9, 142.1, 133.8, 125.8, 117.7, 106.8, 74.3, 60.9, 56.2, 38.7, 33.7, 31.9, 29.5, 29.5, 29.3, 25.3, 22.7, 14.1. MS (EI, 70eV): 392 (11, [M +* ]), 351 (1), 212 (51), 197 (16), 195 (100), 41 (18). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fatty, green, metallic, vibrant, citrus, mandarin leaf. 【0085】 Example 20: Tetradeca-1-en-4-yl 3,4,5-trimethoxybenzoate The compound was prepared using 3,4,5-trimethoxybenzoyl chloride (in place of acetyl chloride) and tetradeca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding tetradeca-1-en-4-yl3,4,5-trimethoxybenzoate (72% yield) as a colorless liquid. 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 7.31 (s, 2H), 5.91 - 5.77 (m, 1H), 5.21 - 5.05 (m, 3H), 3.92 (s, 6H), 3.92 (s, 3H), 2.50 - 2.42 (m, 2H), 1.79 - 1.61 (m, 2H), 1.50 - 1.22 (m, 16H), 0.92 - 0.84 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 165.9, 152.9, 142.1, 133.8, 125.8, 117.7, 106.8, 74.3, 60.9, 56.2, 38.7, 33.7, 31.9, 29.6, 29.5, 29.3, 25.4, 22.7, 14.1. MS (EI, 70eV): 406 (11, [M +* ]), 365 (1), 212 (53), 195 (100). Odor description (1% solution in EtOH on paper blotter, 24h): Green, aldehyde-like, fatty, metallic, citrusy, mandarin leaf. 【0086】 Example 21: Undeca-1-en-4-ylbenzoate Example 21a: Undeca-1-en-4-ol The compound was prepared using octanal (instead of undeca-10-enal) according to the procedure described in Example 1a, yielding undeca-1-en-4-ol (98% yield) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.92 - 5.77 (m, 1H), 5.20 - 5.10 (m, 2H), 3.70 - 3.61 (m, 1H), 2.32 (tddd, J = 1.3, 4.1, 6.6, 13.9 Hz, 1H), 2.21 - 2.09 (m, 1H), 1.67 (br s, 1H), 1.53 - 1.24 (m, 12H), 0.95 - 0.85 (m, 3H).13 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 134.9, 118.0, 70.7, 41.9, 36.8, 31.8, 29.6, 29.3, 25.7, 22.7, 14.1. 【0087】 Example 21b: Undec-1-en-4-yl benzoate The compound was prepared according to the procedure described in Example 1b, using benzoyl chloride (instead of acetyl chloride) and undec-1-en-4-ol (instead of tetradeca-1,13-dien-4-ol), to yield undec-1-en-4-yl benzoate (61% yield) as a colorless liquid. 1 1H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.11 - 8.03 (m, 2H), 7.61 - 7.54 (m, 1H), 7.51 - 7.42 (m, 2H), 5.85 (tdd, J = 7.0, 10.1, 17.1 Hz, 1H), 5.24 - 5.16 (m, 1H), 5.16 - 5.06 (m, 2H), 2.52 - 2.42 (m, 2H), 1.78 - 1.64 (m, 2H), 1.50 - 1.20 (m, 10H), 0.94 - 0.85 (m, 3H). 13 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.2, 133.7, 132.7, 130.7, 129.5, 128.3, 117.7, 74.1, 38.7, 33.7, 31.8, 29.5, 29.2, 25.3, 22.6, 14.1. Description thereon (1% solution in EtOH on paper blotter, 24 h): Green, coriander, aldehyde-like, metallic, fatty, birch leaf. 【0088】 Example 22: Dodec-1-en-4-yl benzoate Example 22a: Dodec-1-en-4-ol The compound was prepared using nonanal (instead of undeca-10-enal) according to the procedure described in Example 1a, yielding dodeca-1-en-4-ol (99% yield) as a pale yellow liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.92 - 5.77 (m, 1H), 5.20 - 5.09 (m, 2H), 3.70 - 3.60 (m, 1H), 2.31 (tddd, J = 1.3, 4.2, 6.6, 13.9 Hz, 1H), 2.20 - 2.09 (m, 1H), 1.69 (d, J = 3.7 Hz, 1H), 1.53 - 1.22 (m, 14H), 0.94 - 0.85 (m, 3H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 134.9, 118.0, 70.7, 41.9, 36.8, 31.9, 29.7, 29.6, 29.3, 25.7, 22.7, 14.1. 【0089】 Example 22b: Dodeca-1-en-4-ylbenzoate The compound was prepared using benzoyl chloride (in place of acetyl chloride) and dodeca-1-en-4-ol (in place of tetradeca-1,13-dien-4-ol) according to the procedure described in Example 1b, yielding dodeca-1-en-4-ylbenzoate (51% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 8.09 - 8.04 (m, 2H), 7.61 - 7.54 (m, 1H), 7.49 - 7.43 (m, 2H), 5.85 (tdd, J = 7.1, 10.2, 17.2 Hz, 1H), 5.24 - 5.16 (m, 1H), 5.16 - 5.05 (m, 2H), 2.53 - 2.43 (m, 2H), 1.80 - 1.62 (m, 2H), 1.48 - 1.20 (m, 12H), 0.94 - 0.84 (m, 3H). 13C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 166.2, 133.7, 132.7, 129.5, 128.3, 117.7, 74.1, 38.7, 33.7, 31.8, 29.5, 29.5, 29.2, 25.3, 22.7, 14.1. Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, metallic, fatty, citrus, mandarin leaf. 【0090】 Example 23: Application in liquid detergent a) Sample preparation 0.2% by weight of the compound according to formula (I) was incorporated into an unscented liquid used as a detergent base for odor substances by magnetic stirring at room temperature for 24 hours. b) Washing test and sensory evaluation A 55g liquid detergent sample was used with a T-shirt made of odor-neutral cotton / elastane blend fabric, and a machine washing cycle at 40°C was performed. The damp and air-dried fabrics (after 1 and 4 days) were evaluated for odor intensity and quality by a panel of 4-6 experts. Odor intensity was recorded on an intensity scale from 0 (odorless) to 5 (very strong). 【0091】 [Table 1] 【0092】 As can be seen in Table 1, all tested materials exhibited a slight odor when stored in a damp state, and over the following days released a fresh aldehyde-like note, resulting in a strong odor impression (score > 3) on dry fabrics, which even increased over time. The odor when stored in a damp state was always nonspecific and resembled the blank odor of fabric washed with an unscented detergent. 【0093】 Example 24: Tetradeca-1,13-diene-4-ylmethanesulfonate A flask was packed with tetradeca-1,13-dien-4-ol (3.00 g, 14.3 mmol), triethylamine (1.73 g, 2.39 mL, 1.2 equivalents, 17.1 mmol), and dichloromethane (DCM) (10 mL), and the mixture was cooled to 5°C. The mixture was then treated dropwise at 5°C with a solution of methanesulfonyl chloride (1.96 g, 1.32 mL, 1.2 equivalents, 17.1 mmol) in DCM (4 mL). After the addition, the condenser was removed, and the yellow suspension was stirred at ambient temperature for 30 minutes. The reaction mixture was then poured into 100 mL of ice-cold 1 M aqueous HCl solution and extracted with MTBE (2 × 100 mL). The organic layer was washed with water and brine until neutral, dried over MgSO4, filtered, and concentrated. The crude material was purified by chromatography on silica gel to obtain tetradeca-1,13-diene-4-ylmethanesulfonate (2.10 g, 51% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 5.91 - 5.73 (m, 2H), 5.22 - 5.14 (m, 2H), 5.05 - 4.92 (m, 2H), 4.75 (quin, J = 6.1 Hz, 1H), 3.01 (s, 3H), 2.56 - 2.41 (m, 2H), 2.12 - 2.00 (m, 2H), 1.79 - 1.63 (m, 2H), 1.50 - 1.24 (m, 12H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 139.2, 132.6, 118.9, 114.1, 82.9, 39.0, 38.8, 34.2, 33.8, 29.4, 29.4, 29.3, 29.1, 28.9, 25.0. MS (EI, 70eV): 209 (1, [M-CH3SO2] +* ), 192 (1), 151 (7), 135 (10), 121 (11), 109 (34), 95 (80), 81 (57), 67 (64), 55 (100), 41 (64). Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, fresh, citrus, mandarin, hot iron, metallic, coriander. 【0094】 Example 25: Tetradeca-1,13-dien-4-yl-4-methylbenzenesulfonate Following the procedure described in Example 24, methanesulfonyl chloride was replaced with p-toluenesulfonyl chloride (3.26 g, 1.2 equivalents, 17.1 mmol) to prepare tetradeca-1,13-dien-4-yl-4-methylbenzenesulfonate (2.20 g, 42% yield) as a colorless liquid. 1 H NMR (400 MHz, CDCl3, 298 K) δ (ppm) = 7.85 - 7.78 (m, 2H), 7.35 (dd, J = 0.7, 8.6 Hz, 2H), 5.83 (tdd, J = 6.6, 10.3, 17.1 Hz, 1H), 5.73 - 5.59 (m, 1H), 5.09 - 4.92 (m, 4H), 4.58 (quin, J = 6.1 Hz, 1H), 2.46 (s, 3H), 2.38 (tddd, J = 1.3, 2.8, 5.8, 7.2 Hz, 2H), 2.09 - 2.01 (m, 2H), 1.64 - 1.53 (m, 2H), 1.43 - 1.33 (m, 2H), 1.33 - 1.12 (m, 12H). 13 C NMR (101 MHz, CDCl3, 298 K) δ (ppm) = 144.4, 139.2, 134.6, 132.3, 129.6, 127.8, 118.6, 114.2, 83.1, 38.8, 33.8, 33.6, 29.3, 29.2, 29.1, 28.9, 24.7, 21.6. Odor description (1% solution in EtOH on paper blotter, 24h): Aldehyde-like, hot iron, citrus, metallic.

Claims

[Claim 1] Equation (I): 【Chemistry 1】 The use of compounds by as fragrance precursors, During the ceremony, X is selected from C and S (=O); R １ is selected from the group consisting of linear or branched C １ ~C １１ alkyl; methoxy; ethoxy; phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, ethoxy; naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, ethoxy; 1-naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, ethoxy; 1-(2-naphthyl)-ethan-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, ethoxy; dialkylamine -NR ５ R ６ (R ５ and R ６ are independently selected from the group consisting of C １ ~C ４ alkyl); and is selected from the group consisting of R ２ This is a linear carbon having a terminal CC double bond. ７ ~C １０ Alkyl and linear C ７ ~C １０ Selected from a group consisting of alkenils; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. The aforementioned use. [Claim 2] The use as a fragrance precursor according to claim 1, wherein the compound of formula (I) is of formula (Ia): 【Chemistry 2】 It is a compound produced by During the ceremony, R １ C is linear or branched １ ~C １１ Alkyl; Methoxy; Ethoxy; Phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-Naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-Naphthyl)-Ethal-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Dialkylamine-NR ５ R ６ (R ５ and R ６ C １ ~C ４ Selected from the group consisting of alkyl (independently selected from the group consisting of alkyl); R ２ This is a linear carbon having a terminal CC double bond. ７ ~C １０ Alkyl and linear C ７ ~C １０ Selected from a group consisting of alkenils; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. The aforementioned use. [Claim 3] The use as a fragrance precursor according to claim 1, wherein the compound of formula (I) is of formula (Ib): 【Transformation 3】 It is a compound produced by During the ceremony, R １ C is linear or branched １ ~C １１ Alkyl; Methoxy; Ethoxy; Phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-Naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-Naphthyl)-Ethal-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Dialkylamine-NR ５ R ６ (R ５ and R ６ C １ ~C ４ Selected from the group consisting of alkyl (independently selected from the group consisting of alkyl); R ２ This is a linear carbon having a terminal CC double bond. ７ ~C １０ Alkyl and linear C ７ ~C １０ Selected from a group consisting of alkenils; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. The aforementioned use. [Claim 4] The compound according to formula (I) is tetradeca-1,13-dien-4-yl acetate, tetradeca-1-en-4-yl acetate, trideca-1-en-4-yl acetate, tetradeca-1-en-4-yl benzoate, trideca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-yl benzoate, tetradeca-1,13-dien-4-yl 2-naphthate, trideca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-(naphthalene-1-yl) acetate, trideca-1-en-4-yl 2-(naphthalene-1-yl) acetate, tetradeca-1,13-dien-4-yl 2-(naphthalene-1-yl) acetate, trideca-1-en The use according to claim 1, selected from the group consisting of -4-yl 2-methylundecanoate, tetradeca-1-en-4-yl 2-methylundecanoate, tetradeca-1-en-4-yldimethylcarbamate, methyltetradeca-1-en-4-yl carbonate, pentadeca-3-en-6-yl acetate, pentadeca-3-en-6-yl benzoate, trideca-1-en-4-yl 3,4,5-trimethoxybenzoate, tetradeca-1-en-4-yl 3,4,5-trimethoxybenzoate, undeca-1-en-4-yl benzoate, dodeca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-ylmethanesulfonate, and tetradeca-1,13-dien-4-yl 4-methylbenzenesulfonate. [Claim 5] Equation (I): 【Chemistry 4】 During the ceremony, X is selected from C and S (=O); R １ It is selected from the group consisting of linear or branched C １ ~C １１ Alkyl; Methoxy; Ethoxy; Phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-Naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-Naphthyl)-Ethal-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Dialkylamine-NR ５ R ６ (R ５ and R ６ C １ ~C ４ Selected from the group consisting of alkyl (independently selected from the group consisting of alkyl); R ２ This is a linear carbon having a terminal CC double bond. ７ ~C １０ Alkyl and linear C ７ ~C １０ Selected from a group consisting of alkenils; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. It is a compound, However, the compounds are not tetradeca-1-en-4-yl acetate, trideca-1-en-4-yl acetate, tetradeca-1,13-diene-4-yl acetate, undeca-1-en-4-yl benzoate, undeca-1-en-4-yl pivalate, and undeca-1-en-4-yl acetate, methylundeca-1-en-4-yl carbonate, dodeca-1,11-diene-4-yl acetate, or dodeca-1-en-4-yl acetate. The aforementioned compound. [Claim 6] The compound according to claim 5, wherein the compound of formula (I) is of formula (Ia) 【Transformation 5】 During the ceremony, R １ C is linear or branched １ ~C １１ Alkyl; Methoxy; Ethoxy; Phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-Naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-Naphthyl)-Ethal-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Dialkylamine-NR ５ R ６ (R ５ and R ６ C １ ~C ４ Selected from the group consisting of alkyl (independently selected from the group consisting of alkyl); R ２ This is a linear carbon having a terminal CC double bond. ７ ~C １０ Alkyl and linear C ７ ~C １０ Selected from a group consisting of alkenils; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. It is a compound produced by The aforementioned compound. [Claim 7] The compound according to claim 5, wherein the compound of formula (I) is of formula (Ib) 【Transformation 6】 During the ceremony, R １ It is selected from the group consisting of linear or branched C １ ~C １１ Alkyl; Methoxy; Ethoxy; Phenyl having up to five substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Naphthyl having up to four substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-Naphthyl-methyl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; 1-(2-Naphthyl)-Ethal-1-yl having up to two substituents independently selected from methyl, ethyl, methoxy, and ethoxy; Dialkylamine-NR ５ R ６ (R ５ and R ６ C １ ~C ４ Selected from the group consisting of alkyl (independently selected from the group consisting of alkyl); R ２ is selected from the group consisting of linear C having a terminal CC double bond ７ to C １０ alkyl and linear C ７ to C １０ alkenyl; R ３ is selected from the group consisting of H, Me, Et, phenyl, 2-naphthyl, and 4-methoxyphenyl; and R ４ This is selected from the group consisting of H and Me. It is a compound produced by The aforementioned compound. [Claim 8] The compounds of formula (I) are tetradeca-1-en-4-ylbenzoate, trideca-1-en-4-ylbenzoate, tetradeca-1,13-dien-4-ylbenzoate, tetradeca-1,13-dien-4-yl 2-naphthate, trideca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-naphthate, tetradeca-1-en-4-yl 2-(naphthalene-1-yl)acetate, trideca-1-en-4-yl 2-(naphthalene-1-yl)acetate, tetradeca-1,13-dien-4-yl 2-(naphthalene-1-yl)acetate, trideca-1-en-4-yl 2-methylundecanoate, tetradeca The compound according to claim 5, selected from the group consisting of -1-en-4-yl 2-methylundecanoate, tetradeca-1-en-4-yldimethylcarbamate, methyltetradeca-1-en-4-yl carbonate, pentadeca-3-en-6-yl acetate, pentadeca-3-en-6-yl benzoate, trideca-1-en-4-yl 3,4,5-trimethoxybenzoate, tetradeca-1-en-4-yl 3,4,5-trimethoxybenzoate, dodeca-1-en-4-yl benzoate, tetradeca-1,13-dien-4-ylmethanesulfonate, and tetradeca-1,13-dien-4-yl 4-methylbenzenesulfonate. [Claim 9] A fragrance composition comprising at least one compound of formula (I) as defined in claim 1. [Claim 10] A consumer product comprising a compound of at least one formula (I) as defined in claim 1, and a consumer product base. [Claim 11] The consumer product according to claim 10, wherein the consumer product is selected from home care products and personal care products. [Claim 12] The consumer product according to claim 11, wherein the consumer product is selected from liquid detergents and shampoos. [Claim 13] A method for releasing a fragrance from a compound according to formula (I) as defined in claim 1, wherein the compound is exposed to an environmental inducer. [Claim 14] A method for producing a compound according to formula (I) as defined in claim 1, comprising the following steps: a) Reacting an aldehyde with allyl magnesium chloride, and b) React the resulting product with an acyl anhydride, acyl chloride, or sulfonyl chloride. Includes, In the formula, steps a) and b) are carried out as a one-pot reaction. The aforementioned method. [Claim 15] A method for imparting, enhancing, improving, or modifying the pleasure properties of a fragrance composition or consumer product, the method comprising, in addition to the composition or consumer product, at least one compound of formula (I) as defined in claim 1. [Claim 16] The method according to claim 15, wherein at least one of the compounds is exposed to an environmental inducer.

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