Alkyl enol ether properfume
Described herein are compounds of formula (I) as properfume compounds. In particular, described herein is a method to release a compound being a ketone 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. Moreover, a perfuming composition and a perfumed consumer product including at least one compound of formula (I) are also described.
1. A method to release from a precursor compound, compounds selected from the group consisting of:
a) a ketone of formula
wherein R 1 represents a C 1-15 alkyl, C 2-15 alkenyl, C 3-15 cycloalkyl, C 5-15 cycloalkenyl or C 6-10 aryl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, hydroxy, carboxylic acid and/or C 1-4 carboxylic ester group;
R 2 represents a C 1-15 alkyl group;
R 1 and R 2 , when taken together, form a C 5-15 cycloalkyl, C 5-15 cycloalkenyl, C 4-14 heterocycloalkyl or C 4-14 heterocycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 2-15 alkenyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid, 4-methylcyclohex-3-en-1-yl and/or C 1-4 carboxylic ester group, the heteroatom represents one or more of an oxygen;
R 4 , each independently, represent a hydrogen or a C 1-5 alkyl group; and
R 1 and R 4 , when taken together, form a C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group;
b) a formate ester of formula
wherein R 3 represents a hydrogen, a C 1-15 alkyl, C 2-15 alkenyl, C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group; and
R 4 has the same meaning as defined above; and
R 3 and R 4 , when taken together, form a C 3-15 cycloalkyl or C 5-15 cycloalkenyl group, each optionally substituted with one or more of a C 1-15 alkyl, C 1-15 alkoxy, C 3-15 cycloalkyl, C 5-15 cycloalkenyl, C 6-10 aryl and/or C 6-10 aryloxy group, each optionally substituted with one or more of a C 1-8 alkyl, C 1-8 alkoxy, carboxylic acid and/or C 1-4 carboxylic ester group; and
c) an alcohol of formula
wherein R 3 and R 4 have the same meaning as defined above;
wherein the precursor compound comprises a compound of formula (I)
wherein R 1 , R 2 , R 3 and R 4 have the same meaning as defined above;
by exposing the precursor compound of formula (I) to an environment wherein the compound is oxidized.
2. The method according to claim 1 , wherein R 1 represents a C 1-10 alkyl group optionally substituted with a C 6 aryl, C 5-7 cycloalkyl and/or C 5-7 cycloalkenyl group, each optionally substituted with one or more of a C 1-4 alkyl and/or C 1-4 alkoxy group.
3. The method according to claim 1 , wherein R 2 represents a C 1-3 alkyl group.
4. The method according to claim 1 , wherein R 3 represents a C 1-10 alkyl, C 3-10 alkenyl or C 5-15 cycloalkyl group, each optionally substituted with one or more of a C 1-4 alkyl, C 6 aryl and/or C 6 aryloxy group.
5. The method according to claim 1 , wherein at least two of the compounds of formula (II), (III) or (IV) are perfuming ingredients.
6. The method according to claim 1 , wherein the environment wherein the compound is oxidized is air.
7. The method according to claim 1 , wherein the method provides a long-lasting odor to the environment.