Organic compounds

Patent metadata

Field	Value
Publication number	US-11020333-B2
Application number	US-201716321653-A
Country	US
Kind code	B2
Filing date	Aug 14, 2017
Priority date	Aug 15, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

The present invention refers to indanone derivatives of formula (I)

wherein
R 1 is selected from hydrogen, methyl and ethyl; R 2 is selected from hydrogen, methyl and ethyl, and R is selected from hydrogen and methyl; or R 2 and R 3 form together with the carbon atoms to which they are attached C 3 -C 5 cycloalkyl; and R 4 is selected from C 2 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 alkoxy, C 3 -C 5 cycloalkyl, and C 3 -C 6 cycloalkenyl.

The invention further refers to perfume compositions and fragrance applications comprising them.

First claim

The invention claimed is:

1. A fragrance composition comprising as odorant a compound of formula (I)

wherein
R 1 is selected from hydrogen, methyl and ethyl;
R 2 is selected from hydrogen, methyl and ethyl, and R 3 is selected from hydrogen and methyl; or
R 2 and R 3 form together with the carbon atoms to which they are attached C 3 -C 5 cycloalkyl;
R 4 is selected from C 2 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 alkoxy, C 3 -C 5 cycloalkyl, and C 3 -C 6 cycloalkenyl;

or a mixture thereof; and a base material.

2. The fragrance composition according to claim 1 wherein the base material is selected from odorant molecules and auxiliary agents.

3. A fragranced article comprising as odorant a compound of formula (I)

wherein
R 1 is selected from hydrogen, methyl and ethyl;
R 2 is selected from hydrogen, methyl and ethyl, and R 3 is selected from hydrogen and methyl; or
R 2 and R 3 form together with the carbon atoms to which they are attached C 3 -C 5 cycloalkyl;
R 4 is selected from C 2 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 alkoxyl, C 3 -C 5 cycloalkyl, and C 3 -C 6 cycloalkenyl;

or a mixture thereof; and a consumer product base.

4. The fragranced article according to claim 3 wherein the consumer product base is selected from fine fragrance, household products, laundry products, body care products, cosmetic products and air care products.

5. The fragranced article according to claim 1 , comprising 0.00001 weight % to 90 weight % of the compound of formula (I), or a mixture thereof, based on the total weight of the article.

6. The fragranced article according to claim 3 comprising at least one compound of formula (I), or a mixture thereof, and at least one ingredient selected from the group consisting of a carrier material and fragrance ingredients.

7. A method of Improving, enhancing or modifying a consumer product base comprising adding to the consumer product base an olfactory acceptable amount of a compound of formula (I)

wherein
R 1 is selected from hydrogen, methyl and ethyl;
R 2 is selected from hydrogen, methyl and ethyl, and R 3 is selected from hydrogen and methyl; or
R 2 and R 3 form together with the carbon atoms to which they are attached C 3 -C 5 cycloalkyl;
R 4 is selected from C 2 -C 5 alkyl, C 2 -C 5 alkenyl, C 1 -C 4 alkoxy, C 3 -C 5 cycloalkyl, and C 3 -C 6 cycloalkenyl;

or a mixture thereof.

8. The method according to claim 7 , wherein the consumer product base is selected from the group consisting of fine fragrance, household products, laundry products, body care products, cosmetic products and air care products.

9. A compound of formula (I)

wherein
R 1 is selected from methyl and ethyl;
R 2 is hydrogen, and R 3 is hydrogen; or
R 2 and R 3 form together with the carbon atoms to which they are attached C 3 -C 5 cycloalkyl;
R 4 is selected from C 3 -C 5 alkyl, C 2 -C 5 alkenyl, C 3 -C 4 alkoxy, C 3 -C 5 cycloalkyl, and C 3 -C 6 cycloalkenyl with the proviso that R 4 is not isopropyl or tert-butyl.

10. The fragranced article according to claim 3 , comprising 0.00001 weight % to 90 weight % of the compound of formula (I), or a mixture thereof, based on the total weight of the article.

11. The fragranced article according to claim 3 , wherein the compound of formula (I) is at least one selected from the group consisting of:
3-methyl-6-propyl-2,3-dihydro-1H-Linden-1-one;
6-isobutyl-2,3-dihydro-1H-Inden-1-one;
6-isopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-(tert-butyl)-2-methyl-2,3-dihydro-1H-inden-1-one;
2,3-dimethyl-6-propyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-3-methyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-2,2-dimethyl-2,3-dihydro-1H-inden-1-one;
6-(tert-butyl)-3-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopentyl-2-methyl-2,3-dihydro-1H-inden-1-one;
2-ethyl-6-isobutyl-2,3-dihydro-1H-inden-1-one;
6-ethyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopentyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-ethoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopropoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propoxy-2,3-dihydro-1H-inden-1-one;
6-isobutoxy-2-methyl-2,3-dihydro-1H-Inden-1-one;
4-isobutyl-6a-methyl-1a,6a-dihydrocyclopropa[a]inden-6(1H)-one;
2-methyl-6-(2-methylallyl)-2,3-dihydro-1H-inden-1-one; and
6-butyl-2-methyl-2,3-dihydro-1H-linden-1-one.

12. The fragrance composition according to claim 1 , wherein the compound of formula (I) is at least one selected from the group consisting of:
3-methyl-6-propyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-2,3-dihydro-1H-inden-1-one;
6-Isopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-(tert-butyl)-2-methyl-2,3-dihydro-1H-inden-1-one;
2,3-dimethyl-6-propyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-3-methyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-2,2-dimethyl-2,3-dihydro-1H-inden-1-one;
6-(tort-butyl)-3-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopentyl-2-methyl-2,3-dihydro-1H-inden-1-one;
2-ethyl-6-isobutyl-2,3-dihydro-1H-inden-1-one;
6-ethyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopentyl-2-methyl-2,3-dihydro-1H-Inden-1-one;
6-ethoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopropoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propoxy-2,3-dihydro-1H-inden-1-one;
6-isobutoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
4-isobutyl-6n-methyl-1a,6a-dihydrocyclopropa[a]inden-6(1H)-one;
2-methyl-6-(2-methylallyl)-2,3-dihydro-1H-Inden-1-one; and
6-butyl-2-methyl-2,3-dihydro-1H-inden-1-one.

13. The method according to claim 7 , wherein the compound of formula (I) is at least one selected from the group consisting of:
3-methyl-6-propyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-2,3-dihydro-1H-inden-1-one;
6-isopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-(tert-butyl)-2-methyl-2,3-dihydro-1H-inden-1-one;
2,3-dimethyl-6-propyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-3-methyl-2,3-dihydro-1H-inden-1-one;
6-isobutyl-2,2-dimethyl-2,3-dihydro-1H-inden-1-one;
6-(tert-buty)-3-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopropyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-cyclopentyl-2-methyl-2,3-dihydro-1H-inden-1-one;
2-ethyl-6-isobutyl-2,3-dihydro-1H-inden-1-one;
6-ethyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopentyl-2-methyl-2,3-dihydro-1H-inden-1-one;
6-ethoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
6-isopropoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
2-methyl-6-propoxy-2,3-dihydro-1H-inden-1-one;
6-isobutoxy-2-methyl-2,3-dihydro-1H-inden-1-one;
4-isobutyl-6a-methyl-1a,6a-dihydrocyclopropa[a]inden-6(1H)-one;
2-methyl-6-(2-methylallyl)-2,3-dihydro-1H-inden-1-one; and
6-butyl-2-methyl-2,3-hydro-1H-inden-1-one.

Assignees

• Givaudan Sa

Inventors

• Zou Yue
• Chai An
• Liu Jie
• Zhou Lijun

Classifications

• C11B9/0049 Primary

  the condensed rings sharing two common C atoms · CPC title

• C11D3/50

  Perfumes · CPC title

• A61L9/01

  Deodorant compositions {(compositions released by contact with a liquid A61L9/05)} · CPC title

• A61K8/35 Primary

  Ketones, e.g. benzophenone · CPC title

• A61K2800/10

  General cosmetic use · CPC title