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US 12,252,465 B2Granted
Enol ether properfume
AssigneeFirmenich SA
InventorsGary Bernard Womack, Brinda Indradas
Life of this patent
Estimating the term…
Abstract
Described herein are compounds of formula (I) as properfume compounds, as well as a method to release a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment wherein it is oxidized. Also described herein are a perfuming composition and a perfume consumer product including at least one compound of formula (I).
Claims15
A method to release, from a precursor compound, compounds selected from the group consisting of
- a) a carbonyl compound of formula
- wherein when R2 represents a OR2′ wherein R2′ represents a C1-12 alkyl group, a C3-12 alkenyl group, a phenethyl group, or a benzyl group, then R1 is a phenyl group optionally substituted by one or two R1′ group wherein R1′, simultaneously or independently, represents a hydroxyl group, a C1-3 alkyl group, a C1-3 alkoxy group, a RaCOO group, a RaOCO group wherein Ra is a hydrogen atom, a C1-3 alkyl group, a C2-3 alkenyl group, or two adjacent RT, when taken together, represent a —O—(CH2)m—O— wherein m is 1 or 2 or form a C5-6 saturated or unsaturated ring;
- when R2 represents a C1-6 alkyl or a C6-10 aryl group each optionally substituted by a hydroxyl group, a C1-3 alkyl group, a C1-3 alkoxy group, then R1 represents a C1-15 alkyl, C3-15 alkenyl, C6-10 aryl, C3-15 cycloalkyl, C5-15 cycloalkenyl or C3-14 heterocycloalkyl group, each optionally substituted with one or more of a C1-15 alkyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, carboxylic acid, C1-4 carboxylic ester, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, hydroxy, carboxylic acid and/or C1-4 carboxylic ester group;
- or
- R1 and R2, when taken together, form a C5-16 cycloalkyl, C5-16 cycloalkenyl, C4-14 heterocycloalkyl or C4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C1-15 alkyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, carboxylic acid and/or C1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom;
- b) a formate ester of formula
- wherein n represents an integer between 1 and 5;
- R3, simultaneously or independently, represents at least one substituent of the aromatic ring and is a C1-6 alkyl group optionally substituted by a hydroxy, C1-6 alkoxy or oxo group;
- a C4-7 oxacycloalkyl or oxacycloalkenyl group optionally substituted with a C1-3 alkyl or a methylene group;
- a C2-6 alkenyl group;
- a C1-6 alkoxy group;
- or a RbOCO group wherein Rb is a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C3-7 cycloalkyl group, a benzyl group or a phenethyl group;
- and
- c) an alcohol of formula
- wherein R3 has the same meaning as defined above;
- wherein the precursor compound comprises a compound of formula (I)
- in the form of any one of its stereoisomers or a mixture thereof, and wherein n,
- R1, R2 and R3 have the same meaning as defined above;
- the method comprising exposing the precursor compound of formula (I) to an environment wherein the compound is oxidized.
16 more elements
A compound of formula
- in the form of any one of its stereoisomers or a mixture thereof and wherein when R2 represents a OR2′ wherein R2′ represents a C1-12 alkyl group, a C3-12 alkenyl group, phenethyl group, or a benzyl group, then R1 is a phenyl group optionally substituted by one or two RT group wherein R1′, simultaneously or independently, represents a hydroxyl group, a C1-3 alkyl group, a C1-3 alkoxy group or a RaCOO group, a RaOCO group wherein Ra is a hydrogen atom, a C1-3 alkyl group, a C2-3 alkenyl group, or two adjacent R1′, when taken together, represent a —O—(CH2)m—O— wherein m is 1 or 2 or form a C5-6 saturated or unsaturated ring;
- when R2 represents a C1-3 alkyl, then R1 represents a C1-15 alkyl, C2-15 alkenyl, C6-10 aryl, C3-15 cycloalkyl, C5-15 cycloalkenyl or C3-14 heterocycloalkyl group, each optionally substituted with one or more of a C1-15 alkyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, carboxylic acid, C1-4 carboxylic ester, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, hydroxy, carboxylic acid and/or C1-4 carboxylic ester group;
- or
- R1 and R2, when taken together, form a C5-16 cycloalkyl, C5-16 cycloalkenyl, C4-14 heterocycloalkyl or C4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C1-15 alkyl, C1-15 alkoxy, C3-15 cycloalkyl, C5-15 cycloalkenyl, C6-10 aryl and/or C6-10 aryloxy group, each optionally substituted with one or more of a C1-8 alkyl, C1-8 alkoxy, carboxylic acid and/or C1-4 carboxylic ester group, wherein the heteroatom represents one or more of an oxygen atom;
- n represents an integer between 1 and 3;
- R3, simultaneously or independently, represents at least one substituent of the aromatic ring and is a C1-6 alkyl group optionally substituted by a hydroxy, C1-6 alkoxy, or oxo group;
- a C2-6 alkenyl group;
- a C1-6 alkoxy group;
- or a RbOCO group wherein Rb is a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C3-7 cycloalkyl group, a benzyl group or a phenethyl group;
- provided that
- when R1 is methyl then R2 is not methyl,
- when R1 is ethyl then R2 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.
10 more elements
Dependencies are inferred from the claim text.