Substituted cyclopentyl- and cyclohexyl-derivatives useful for perfumery

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

wherein

n is 1 or 2;

R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, and C 3 -C 5 alkyl; or

R 1 and R 2 form together with the carbon atom to which they are attached C 3 -C 6 cycloalkyl; or

R 1 and R 2 form together methylidene;

R 3 is selected from hydrogen, and C 1 -C 3 alkyl;

R 4 is selected from hydrogen, and C 1 -C 3 alkyl; and

X is CN; or

X is —C(O)OR 5 , wherein R 5 is selected from the group consisting of methyl, ethyl, C 3 -C 5 alkyl, vinyl and C 3 -C 5 alkenyl;

with the proviso that

a) at least two of the residues R 1 , R 2 and R 3 are not hydrogen;

b) when R 3 is hydrogen, R 4 is selected from C 1 -C 3 alkyl;

c) when X is —CN, and R 1 , R 2 and R 3 are methyl, then R 4 is not hydrogen.

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),

wherein

n is 1 or 2;

R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, and C 3 -C 5 alkyl; or

R 1 and R 2 form together with the carbon atom to which they are attached C 3 -C 6 cycloalkyl; or

R 1 and R 2 form together methylidene;

R 3 is selected from hydrogen, and C 1 -C 3 alkyl;

R 4 is selected from hydrogen, and C 1 -C 3 alkyl; and

X is —CN; or

X is —C(O)OR 5 , wherein R 5 is selected from the group consisting of methyl, ethyl, C 3 -C 5 alkyl, vinyl and C 3 -C 5 alkenyl;

with the proviso that

a) at least two of the residues R 1 , R 2 and R 3 are not hydrogen;

b) when R 3 is hydrogen, R 4 is selected from C 1 -C 3 alkyl;

c) when X is —CN, and R 1 , R 2 and R 3 are methyl, then R 4 is not hydrogen;

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 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),

wherein

n is 1 or 2;

R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, and C 3 -C 5 alkyl; or

R 1 and R 2 form together with the carbon atom to which they are attached C 3 -C 6 cycloalkyl; or

R 1 and R 2 form together methylidene;

R 3 is selected from hydrogen, and C 1 -C 3 alkyl;

R 4 is selected from hydrogen, and C 1 -C 3 alkyl; and

X is —CN; or

X is —C(O)OR 5 , wherein R 5 is selected from the group consisting of methyl, ethyl, C 3 -C 5 alkyl, vinyl and C 3 -C 5 alkenyl;

with the proviso that

a) at least two of the residues R 1 , R 2 and R 3 are not hydrogen;

b) when R 3 is hydrogen, R 4 is selected from C 1 -C 3 alkyl;

c) when X is —CN, and R 1 , R 2 and R 3 are methyl, then R 4 is not hydrogen.

6. A compound of formula (I),

wherein

n is 1 or 2;

R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, and C 3 -C 5 alkyl; or

R 1 and R 2 form together with the carbon atom to which they are attached C 3 -C 6 cycloalkyl;

R 3 is selected from hydrogen, and C 1 -C 3 alkyl;

R 4 is selected from hydrogen, and C 1 -C 3 alkyl; and

X is —CN; or

X is —C(O)OR 5 , wherein R 5 is selected from the group consisting of methyl, ethyl, C 3 -C 5 alkyl, vinyl and C 3 -C 5 alkenyl;

with the proviso that

a) at least two of the residues R 1 , R 2 and R 3 are not hydrogen;

b) when R 3 is hydrogen, R 4 is selected from C 1 -C 3 alkyl;

c) when X is —CN, and R 1 , R 2 and R 3 are methyl, then R 4 is not hydrogen;

d) when n is 2; R 1 and R 2 are not hydrogen.

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.