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US 2004/0171516 A1Published application
Precursors for ketones and aldehydes
AssigneeGivaudan SA
InventorsSamuel Derrer, Markus Gautschi
Life of this patent
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Abstract
The present invention refers to compounds of formula I 1 as precursors for a ketone of formula II, 2 an aldehyde or ketone of formula III, and an aldehyde or ketone of formula IV, 3 These compounds are useful in perfumery, especially in the fine and functional perfumery.
Claims19
Use of a compound of the formula I
- 70
- as precursor for a ketone of the formula II,
- 71
- an aldehyde or ketone of the formula III comprising up to 20 carbon atoms, and
- 72
- an aldehyde or ketone of the formula IV comprising up to 20 carbon atoms,
- 73
- wherein
- A is an aromatic or a heteroaromatic ring;
- or
- A is an aromatic or heteroaromatic ring substituted with one or more residues selected from the group of alkyl, aryl, aralkyl, alkenyl, alkynyl, —OH, —O-alkyl, -alkoxyalkoxy, —O-aralkyl, —O-aryl, —O-acyl, —NO2, —NH2, —NH-alkyl, —N(alkyl)2, —NH-acyl, —N(acyl)2, —CN, —SH, —S-alkyl, —S-aryl and a halogen atom, selected from fluorine, chlorine or bromine;
- or
- A is an aromatic or heteroaromatic ring bearing a residue that together with the carbon atoms to which it is attached forms an aromatic or alicyclic ring, or an aromatic or alicyclic ring bearing one or more heteroatoms selected from oxygen, nitrogen or sulphur, which aromatic or alicyclic ring may be substituted with one or more residues selected from the group of alkyl, alkenyl, and alkynyl residues,
- R1 represents hydrogen, alkyl, alkenyl, alkynyl, acyl or aryl residues, and said residues may comprise one or more oxygen atom(s),
- R2, R3, R4, R5 represent independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aromatic residues, and said residues may comprise one or more oxygen atom(s),
- R2 and R3 together with the carbon atom to which they are attached may form a 4 to 18 membered carbocyclic ring optionally substituted by an alkyl, alkenyl or alkynyl residue having up to 10 carbon atoms, and the ring and residues may comprise one or more oxygen atom(s),
- R4 and R5 together with the carbon atom to which they are attached may form a 4 to 18 membered carbocyclic ring optionally substituted by an alkyl, alkenyl or alkynyl residue having up to 10 carbon atoms, and the ring and residues may comprise one or more oxygen atom(s), and
- n is an integer from 1 to 3.
15 more elements
Use of a compound of formula I according one of the preceding claims, wherein n=1 and R1=H.
Use of a compound of formula I according to any one of the preceding claims, wherein R2 and R4 are the same, and R3 and R5 are the same.
A compound of formula I
- 74
- wherein n is 1,
- R1 is H, methyl, phenyl,
- A is phenyl, 6-tert-butyl-1,1-dimethyl-indan-4-yl, 2,4-dimethylphenyl, 3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl, 5,6,7,8-tetrahydro-2-naphthalenyl, 1,1,2,3,3-pentamethyl-indan-5-yl, 2-naphthalenyl, 1,1,2,3,3,6-hexamethyl-indan-5-yl, 1,1,2,6-tetra-methyl-3-(1-methylethyl)-indan-5-yl, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl, 3-ethyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl, 4-alkoxy-phenyl, 4-dialkylamino-phenyl, 4-acylamino-phenyl, 4-diacylamino-phenyl, 3,4-(methylenedioxy)-phenyl, 3,4-dialkoxy-phenyl, 4-(2-methoxyethoxy)-phenyl, 3,4-di-(2-methoxyethoxy)-phenyl, 4-[2-(2-methoxyethoxy)-ethoxy]-phenyl, 3,4-di-[2-(2-methoxyethoxy)-ethoxy]-phenyl, 2,3-dihydro-benzo[1,4]dioxin-6-yl,
- R2 and R4 are hydrogen, and
- R3═R5 are 6,10-dimethylundec-9-ene-2-yl, 2,4-dimethyl-cyclohex-3-ene-1-yl, 1,3,5-trimethyl-cyclohex-1-ene-4-yl, 4-(4-hydroxy-4-methyl-pentyl)-cyclohex-3-ene-1-yl, pent-1-enyl, hexyl, 6-methyl-hept-5-ene-2-yl, nonyl, 2-decyl, 9-decenyl, decyl, undecyl, 2-undecyl, heptyl, octyl, 8-decenyl, 1-phenyl-ethyl, (4-methyl-phenyl)-methyl, 2,6-dimethyl-heptyl, 2,6,10-trimethyl-undeca-5,9-dienyl, 2,6-dimethyl-6-hydroxy-heptyl, 2-(3-isopropyl-phenyl)-propyl, 4-(4-methyl-pent-3-enyl)-cyclohex-3-ene-1-yl, 4-(2,6,6-trimethylcyclohex-2-en-1-yl)-2-butyl, 3-(4-tert-butylphenyl)-2-propyl, 2-(4-tert-butylphenyl)-ethyl, 3-(benzo[1,3]dioxol-5-yl)-2-propyl, 2,6-dimethyl-5-heptenyl, 3-(p-isopropyl-phenyl)-2-propyl, (3,7-dimethyl-oct6-enyloxy)-methyl, (5Z)-octa-1,5-dienyl, 1-nonenyl, 1-undecenyl, 2,6-dimethyl-hepta-1,5-dienyl, 2,6-dimethyl-octa-1,5-dienyl, or
- R2 and R4 are methyl, and
- R3═R5 are pentyl, hexyl, heptyl, octyl, nonyl, 2-phenyl-ethyl, 4-methyl-pent-3-ene-1-yl, 4,8-dimethyl-nona-3,7-dien-1-yl, (2,6,6-trimethylcyclohex-1-ene-1-yl)-ethyl, (2,6,6-trimethyl cyclohex-1-ene-2-yl)-ethyl, 2-(4-hydroxyphenyl)-ethyl, (1,3-benzodioxole-5-yl)-ethyl, or
- R2 and R4 are ethyl, and
- R3═R5 are 5-methyl-hex-4-en-2-yl, or
- R2CHR3═R4CHR5 are 2-heptyl-cyclopentyl, 7-methyl-3,4-dihydro-2H-1,5-benzodioxepin-3-yl, 3-methyl-cyclopentadecyl, cyclopentadecyl, 5-cyclohexadecen-1-yl, 4-(1,1-dimethylpropyl)-cyclohexyl, 2-(2-methylethyl)-5-methyl-cyclohexyl, 2-(1-methylethyl)-5-methyl-cyclohexyl, 2-(butan-2-yl)-cyclohexyl, 3-(2-oxo-propyl)-2-pentyl-cyclopentyl, 2-pentyl-3-(methoxycarbonylmethyl)-cyclopentyl.
8 more elements
Dependencies are inferred from the claim text.