Substituted bicyclo [4.1.0] heptane-7-carboxylic acid amides and derivatives thereof as food flavor substances

1. The compound of the Formula (II),

wherein;

R 1 , R 3 , R 5 and R 7 denote in each case independently of one another hydrogen, an alkyl radical with 1 to 6 C atoms or an alkenyl radical with 2 to 6 C atoms,

with the proviso that at least one of the radicals R 1 and R 7 and a further one of the radicals R 1 , R 3 , R 5 and R 7 are not hydrogen,

wherein independently of one another also two of the radicals R 1 , R 3 , R 5 and R 7 may jointly form a bridge with one or more bridge C atoms,

Y 1 and Y 2 denote independently of one another hydrogen, methyl or ethyl,

and

R a and R b denote independently of one another hydrogen, an alkyl radical with 1 to 6 C atoms, an alkenyl radical with 2 to 6 C atoms or a cycloalkyl radical with 3 to 6 C atoms,

with the exception of the compounds selected from the group consisting of:

2,4-dimethylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (2S,5R)-2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (exo) (1R,2S,4S,5S)-tricyclo[3.2.1.0 2,4 ]octane-3-carboxylic acid amide, (1R,2R,4R,7R)-4,8,8-trimethyltricyclo[5.1.0.0 2,4 ]octane-3-carboxylic acid amide, 2,7,7-trimethyltricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide, 4,7,7-trimethyl-tricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide, (exo) (1aR,2R,2aS,5aR,6S,6aS)-decahydro-2,6-methanocyclopropa[f]indene-1-carboxamide and exo-tricyclo[3.2.1.0 2,4 ]octane-3-anti-carboxylic acid dimethyl amide.

2. The compound of claim 1 , wherein:

Y 1 and Y 2 denote independently of one another hydrogen or methyl,

with the exception of the compounds selected from the group consisting of:

2,4-dimethylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (2S,5R)-2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (exo) (1R,2S,4S,5S)-tricyclo[3.2.1.0 2,4 ]octane-3-carboxylic acid amide; (1R,2R,4R,7R)-4,8,8-trimethyltricyclo[5.1.0.0 2,4 ]octane-3-carboxylic acid amide; 2,7,7-trimethyltricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide and 4,7,7-trimethyl-tricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide.

3. The compound of claim 1 , wherein the compound

is a compound of the Formula (III),

wherein:

R 1 and R 5 denote independently of one another in each case an alkyl radical with 1 to 6 C atoms or jointly denote a bridge with one or more bridge C atoms,

with the exception of:

2,4-dimethylbicyclo[4.1.0]heptane-7-carboxylic acid amide, 2,7,7-trimethyltricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide and 4,7,7-trimethyl-tricyclo[4.1.1.0 2,4 ]octane-3-carboxylic acid amide;

or

a compound of the Formula (IV)

wherein:

R 1 and R 7 denote independently of one another in each case an alkyl radical with 1 to 6 C atoms or are covalently bonded to one another,

wherein in Formula (III) and Formula (IV):

R a and R b denote independently of one another hydrogen, an alkyl radical with 1 to 6 C atoms, an alkenyl radical with 2 to 6 C atoms or a cycloalkyl radical with 3 to 6 C atoms,

with the exception of the compounds selected from the group consisting of:

(2S,5R)-2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxylic acid amide, (exo) (1R,2S,4S,5S)-tricyclo[3.2.1.0 2,4 ]octane-3-carboxylic acid amide and exo-tricyclo[3.2.1.0 2,4 ]octane-3-anti-carboxylic acid dimethyl amide.

4. The compound of claim 3 , wherein R 1 and R 5 in Formula (III) as well as R 1 and R 7 in Formula (IV)

denote independently of one another in each case methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methyl-butyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethyl-propyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl or 1,2,2-trimethylpropyl,

or

together denote a —CH 2 —, —C(CH 3 ) 2 —, —CH 2 CH 2 — or —CH═CH— bridge,

with the exception of the compounds selected from the group consisting of:

2,4-dimethylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (2S,5R)-2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxylic acid amide and (exo) (1R,2S,4S,5S)-tricyclo[3.2.1.0 2,4 ]octane-3-carboxylic acid amide.

5. The compound of claim 3 , wherein:

R a and R b denote independently of one another hydrogen or an alkyl radical with 1 to 6 C atoms, selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethyl-propyl and 1,2,2-trimethylpropyl

or

an alkenyl radical with 2 to 6 C atoms

or

a cycloalkyl radical with 3 to 6 C atoms,

with the exception of the compounds selected from the group consisting of:

2,4-dimethylbicyclo[4.1.0]heptane-7-carboxylic acid amide; (2S,5R)-2-isopropyl-5-methylbicyclo[4.1.0]heptane-7-carboxylic acid amide and (exo) (1R,2S,4S,5S)-tricyclo[3.2.1.0 2,4 ]octane-3-carboxylic acid amide.

6. The compound of claim 3 , wherein:

R a denotes hydrogen, and

R b denotes an alkyl radical with 1 to 6 C atoms, selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2-trimethylpropyl and 1,2,2-trimethylpropyl,

or

an alkenyl radical with 2 to 6 C atoms

or

a cycloalkyl radical with 3 to 6 atoms,

or

R a and R b both denote methyl.

7. The compound of claim 3 , wherein the compound of the Formula (IV) is a compound of the Formula (IVa)

8. The compound of claim 3 , wherein the compound of the Formula (IV) is a compound of the Formula (IVc)

9. The compound of claim 3 , wherein the compound of the Formula (IV) is a compound of the Formula (E1) and/or (E2)

and/or (B1) and/or (B2)

and/or (P1) and/or (P2)

and/or (P3) and/or (P4)

and/or (H1) and/or (H2)

10. The compound according to claim 7 , wherein the compound of Formula (IV) is one of the two enantiomeric compounds of the Formula (IVa)