Organic Compounds

• US 20100292128A1
• Filed: 06/09/2008
• Published: 11/18/2010
• Est. Priority Date: 06/11/2007
• Status: Active Grant

• Current Assignee: Givaudan SA
• Original Assignee: Givaudan SA
• Inventors: Trunz, Bernadette Bourdin, Anorga, Nicolas, Granier, Thierry, Gautschi, Markus
• Granted Patent: US 9,012,391 B2
• Time in Patent Office: Days
• US Class Current: 512/9
• CPC Class Codes: C07C 2602/50 Spiro compounds
• CPC Class Codes: C07C 45/65 by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
• CPC Class Codes: C07C 49/323 having keto groups bound to condensed ring systems
• CPC Class Codes: C07C 49/553 polycyclic
• CPC Class Codes: C07C 49/557 having unsaturation outside the rings
• CPC Class Codes: C07C 67/317 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
• CPC Class Codes: C07C 69/753 of polycyclic acids
• CPC Class Codes: C11B 9/0057 Spiro compounds

Abstract

Described are spiroalkyl- and -alkenylketones and esters thereof, a method for their production and fragrance compositions comprising them.

Claims

1. A fragrance compound according to formula (I)

2. A fragrance compound according to claim 1 wherein the compound of formula (I) is selected from the group consisting of:

(E)-1-(7-methylspiro[4.5]dec-8-en-6-yl)but-2-en-1-one;

methyl 7-methylspiro[4.5]dec-8-ene-6-carboxylate;

ethyl 7-methylspiro[4.5]dec-8-ene-6-carboxylate;

allyl 7-methylspiro[4.5]dec-8-ene-6-carboxylate;

methyl 7-methylspiro[4.5]decane-6-carboxylate;

ethyl 7-methylspiro[4.5]decane-6-carboxylate;

1-(7-methylspiro[4.5]decan-6-yl)butan-1-one;

1-(7-methylspiro[4.5]dec-8-en-6-yl)butan-1-one;

(E)-1-(7-methylspiro[4.5]decan-6-yl)but-2-en-1-one;

(E)-1-(spiro[4.5]dec-6-en-6-yl)but-2-en-1-one;

(E)-1-(5-methylspiro[2.5]oct-6-en-4-yl)but-2-en-1-one;

(E)-1-(5-methylspiro[2.5]oct-5-en-4-yl)but-2-en-1-one;

ethyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate;

(E)-1-(7-methylspiro[4.5]dec-7-en-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]dec-6-en-6-yl)but-2-en-1-one;

ethyl 7-methylenespiro[4.5]dec-8-ene-6-carboxylate;

ethyl 7-methylspiro[4.5]deca-6,8-diene-6-carboxylate;

ethyl 7-methylspiro[4.5]deca-7,9-diene-6-carboxylate;

(2-methylcyclopropyl)(7-methylspiro[4.5]dec-8-en-6-yl)methanone;

methyl 7-methylspiro[4.5]dec-7-ene-6-carboxylate;

methyl 7-methylspiro[4.5]dec-6-ene-6-carboxylate;

ethyl 7-methylspiro[4.5]dec-6-ene-6-carboxylate;

(E)-1-(7-methylspiro[4.5]dec-6-en-6-yl)but-2-en-1-one;

methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate;

ethyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate;

(E)-1-(7-methylspiro[4.5]dec-9-en-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]deca-6,8-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]deca-7,9-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylenespiro[4.5]dec-8-en-6-yl)but-2-en-1-one;

methyl 2-methylspiro[4.4]non-1-ene-1-carboxylate;

ethyl 2-methylspiro[4.4]non-1-ene-1-carboxylate;

(E)-1-(2-methylspiro[4.4]non-1-en-1-yl)but-2-en-1-one;

methyl 2-methylspiro[4.4]non-2-ene-1-carboxylate;

ethyl 2-methylspiro[4.4]non-2-ene-1-carboxylate;

(E)-1-(2-methylspiro[4.4]non-2-en-1-yl)but-2-en-1-one;

cyclopropyl(7-methyl-spiro[4.5]dec-8-en-6-yl)methanone;

(2-methylcyclopropyl)(7-methylspiro[4.5]deca-6,8-dien-6-yl)methanone;

cyclopropyl(7-methylspiro[4.5]deca-6,8-dien-6-yl)methanone;

methyl 7-ethylidenespiro[4.5]decane-6-carboxylate;

ethyl 7-ethylidenespiro[4.5]decane-6-carboxylate;

(2E)-1-(7-ethylidenespiro[4.5]decan-6-yl)but-2-en-1-one;

methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate;

methyl 7-methylspiro[4.5]deca-6,8-diene-6-carboxylate;

methyl 7-methylenespiro[4.5]dec-8-ene-6-carboxylate;

ethyl 7-methylenespiro[4.5]decane-6-carboxylate;

methyl 7-methylenespiro[4.5]decane-6-carboxylate;

(E)-1-(7-methylenespiro[4.5]decan-6-yl)but-2-en-1-one;

(E)-1-(spiro[4.5]deca-2,6-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]deca-2,6-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]deca-2,7-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylspiro[4.5]deca-2,8-dien-6-yl)but-2-en-1-one;

(E)-1-(7-methylenespiro[4.5]dec-2-en-6-yl)but-2-en-1-one; and

(E)-1-(7-methylspiro[4.5]deca-2,6,8-trien-6-yl)but-2-en-1-one.

3. A fragrance composition comprising a compound of formula (I) according to claim 1.

4. A method of manufacturing a fragrance application, comprising the step of:

incorporating a compound of formula (I) according to claim 1 into a consumer product base.

9. A fragrance composition comprising a compound of formula (I) according to claim 2.

10. A method of manufacturing a fragrance application, comprising the step of:

incorporating a compound of formula (I) according to claim 2 into a consumer product base.

5. A compound according to formula (I)

7. A method of producing a compound of formula (I)