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US 6,645,932 B2Granted
Chemical compounds and perfume compositions
AssigneePFW Aroma Chemical B.V.
InventorsWillem Lenselink, Anton Pieter J. van Manen
Life of this patent
Estimating the term…
Abstract
The invention relates to new chemical compounds useful as perfumes or as components of perfumes. More specifically it relates to alkyl-substituted 2-acylindenes and isomeric mixtures thereof, as well as to perfume compositions comprising said compounds. Furthermore, the invention relates to the use of said compounds and methods of making said compounds.
Claims14
An indene of Formula I:
- wherein R1, R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 and R8 together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less, with the proviso that R1 and R2 together do not represent a tetramethylene moiety if R3, R4, R5, R6, R7 and R8 all represent hydrogen, and with the proviso that R3 does not represent hydrogen if R1, R2, R4, R5, R6, R7 and R8 all represent a methyl group.
A fragrance composition comprising an indene compound of Formula I,
- wherein R1 and R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 or R8 together may represent a di-, tri-, tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri-, tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less.
A fragrance composition comprising an indene of Formula I:
- wherein R1, R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 and R8 together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less, with the proviso that R1 and R2 together do not represent a tetramethylene moiety if R3, R4, R5, R6, R7 and R8 all represent hydrogen, and with the proviso that R3 does not represent hydrogen if R1, R2, R4, R5, R6, R7 and R8 all represent a methyl group.
A method of forming a fragrance composition comprising mixing a natural oil, synthetic oil, alcohol, aldehyde, ketone, ester, lactone, ether, hydrocarbon or nitrile with an idene of Formula I:
- wherein R1, R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 and R8 together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less, with the proviso that R1 and R2 together do not represent a tetramethylene moiety if R3, R4, R5, R6, R7 and R8 all represent hydrogen, and with the proviso that R3 does not represent hydrogen if R1, R2, R4, R5, R6, R7 and R8 all represent a methyl group.
A method of enhancing and/or reinforcing the aroma characteristics of natural or synthetic materials comprising mixing natural or synthetic materials with an indene of Formula 1:
- wherein R1, R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 and R8 together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less, with the proviso that R1 and R2 together do not represent a tetramethylene moiety if R3, R4, R5, R6, R7 and R8 all represent hydrogen, and with the proviso that R3 does not represent hydrogen if R1, R2, R4, R5, R6, R7 and R8 all represent a methyl group.
A method for producing an indene compound comprising the selective formylation or acylation of an alkene moiety of an indene of Formula II:
- wherein R1, R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 or R8 together may represent a di-, tri-or tetra- or pentamethylene moiety or a lower alkyl-substituted di, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, with the proviso the R1 and R2 together do not represent a tetramethylene moiety if R3, R4, R5, R6, R7 and R8 all represent hydrogen, and with the proviso that R3 does not represent hydrogen if R1, R2, R4, R5, R6, R7 and R8 all represent a methyl group.
A method for producing an indene compound of Formula I:
- wherein R1 and R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 or R8 together may represent a di-, tri-, tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri-, tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms is twenty two or less, comprising the conversion under Friedel Crafts acylation conditions of indanes of Formula III:
- wherein R1 and R2 each represent a lower alkyl group and R3, R4, R5, R6, R7 and R8 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7 or R8 together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-,tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group and wherein R9, R10, R11, R12, and R13 each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, or R13 or together represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms in formula III is fifty or less.
Dependencies are inferred from the claim text.