Substituted cyclopentyl- and cyclohexyl-derivatives useful for perfumery

• US 10,640,460 B2
• Filed: 12/08/2016
• Issued: 05/05/2020
• Est. Priority Date: 12/10/2015
• Status: Active Grant

• Current Assignee: Givaudan SA
• Original Assignee: Givaudan SA
• Inventors: Baumgartner, Corinne
• Primary Examiner(s): Lu, Caixia
• Application Number:
  US15/779,982
• Publication Number:
  US 20180346412A1
• Time in Patent Office: 1,244 Days
• CPC Class Codes: C07C 255/31 having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 2602/50 Spiro compounds
• CPC Class Codes: C07C 69/608 Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
• CPC Class Codes: C11B 9/0019 carbocylic acids; Salts or esters thereof
• CPC Class Codes: C11B 9/0023 containing nitrogen as the only heteroatom
• CPC Class Codes: C11B 9/003 the ring containing less than six carbon atoms
• CPC Class Codes: C11B 9/0034 the ring containing six carbon atoms

Abstract

The present invention refers to substituted cyclopentyl- and cyclohexyl-derivatives of formula (I)

• • wherein n, R¹, R², R³, R⁴ and X have the same meaning as given in the description.

The invention further refers to fragrance compositions and fragranced articles comprising them.

Claims

1. A method comprising using as a fragrance alone or combining with a base material in a fragranced article, a compound of formula (I)

2. The method according to claim 1 wherein the compound of formula (I) is selected from the group consisting of

ethyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

methyl 2-(1,2,2-trimethylcyclopentyl)acetate,

methyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

propyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

isopropyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

but-3-en-1-yl 2-(1,2,2-trimethylcyclopentyl)propanoate,

isobutyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

allyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

methyl 2-(1-methylspiro[4.4]nonan-1-yl)acetate,

methyl 2-(1-methylspiro[4.4]nonan-1-yl)propanoate,

ethyl 2-(1-methylspiro[4.4]nonan-1-yl)acetate,

ethyl 2-(1-methylspiro[4.4]nonan-1-yl)propanoate,

ethyl 2-(1-methyl-2-methylenecyclopentyl)propanoate,

ethyl 2-(4-methylspiro[2.4]heptan-4-yl)propanoate,

ethyl 2-(2-ethyl-1,2-dimethylcyclopentyl)acetate,

ethyl 2-(2-ethyl-1,2-dimethylcyclopentyl)propanoate,

ethyl 2-(1,2-dimethyl-2-propylcyclopentyl)propanoate,

ethyl 2-(1,2,2-trimethylcyclopentyl)acetate,

ethyl 2-(1,2,2-trimethylcyclopentyl)butanoate,

ethyl 2-(1,2,2-trimethylcyclopentyl)pentanoate,

ethyl 2-(1-ethyl-2,2-dimethylcyclopentyl)propanoate,

ethyl 2-(1,2-dimethylcyclopentyl)propanoate,

2-(1,2,2-trimethylcyclopentyl)propanenitrile,

2-(2-ethyl-1,2-dimethylcyclopentyl)acetonitrile,

ethyl 2-(2,2-dimethylcyclopentyl)propanoate,

ethyl 2-(2,2-dimethylcyclohexyl)propanoate,

ethyl 2-(1,2,2-trimethylcyclohexyl)acetate, and

ethyl 2-(1,2,2-trimethylcyclohexyl)propanoate.

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

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

5. A method of improving, enhancing or modifying a consumer product base by means of addition thereto of an olfactory acceptable amount of a compound of formula (I),

6. A compound of formula (I),

7. The compound according to claim 6 selected from the group consisting of

ethyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

methyl 2-(1,2,2-trimethylcyclopentyl)acetate,

methyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

propyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

isopropyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

but-3-en-1-yl 2-(1,2,2-trimethylcyclopentyl)propanoate,

isobutyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

allyl 2-(1,2,2-trimethylcyclopentyl)propanoate,

methyl 2-(1-methylspiro[4.4]nonan-1-yl)acetate,

methyl 2-(1-methylspiro[4.4]nonan-1-yl)propanoate,

ethyl 2-(1-methylspiro[4.4]nonan-1-yl)acetate,

ethyl 2-(1-methylspiro[4.4]nonan-1-yl)propanoate,

ethyl 2-(1-methyl-2-methylenecyclopentyl)propanoate,

ethyl 2-(4-methylspiro[2.4]heptan-4-yl)propanoate,

ethyl 2-(2-ethyl-1,2-dimethylcyclopentyl)acetate,

ethyl 2-(2-ethyl-1,2-dimethylcyclopentyl)propanoate,

ethyl 2-(1,2-dimethyl-2-propylcyclopentyl)propanoate,

ethyl 2-(1,2,2-trimethylcyclopentyl)acetate,

ethyl 2-(1,2,2-trimethylcyclopentyl)butanoate,

ethyl 2-(1,2,2-trimethylcyclopentyl)pentanoate,

ethyl 2-(1-ethyl-2,2-dimethylcyclopentyl)propanoate,

ethyl 2-(1,2-dimethylcyclopentyl)propanoate,

2-(1,2,2-trimethylcyclopentyl)propanenitrile,

2-(2-ethyl-1,2-dimethylcyclopentyl)acetonitrile,

ethyl 2-(2,2-dimethylcyclopentyl)propanoate,

ethyl 2-(2,2-dimethylcyclohexyl)propanoate,

ethyl 2-(1,2,2-trimethylcyclohexyl)acetate, and

ethyl 2-(1,2,2-trimethylcyclohexyl)propanoate.