Compounds capable of releasing fragrant compounds

Patent metadata

Field	Value
Publication number	US-9193935-B2
Application number	US-201113996158-A
Country	US
Kind code	B2
Filing date	Dec 23, 2011
Priority date	Dec 23, 2010
Publication date	Nov 24, 2015
Grant date	Nov 24, 2015

Abstract

Provided is class of compounds of formula (I)

wherein X, R 1 , R 2 and R 3 have the same meaning as given in the specification capable of releasing fragrant compounds in a controlled manner into the surroundings.

First claim

The invention claimed is:

1. A method comprising providing a compound of formula (I)

as precursor for generating in the presence of molecular oxygen a ketone or aldegyde of the formula (II)

and a carbonyl compound of the formula (III)

and exposing the precursor to oxygen;
wherein
R 1 is selected from the group consisting of
C 5 -C 14 alkyl, C 5 -C 14 alkenyl,
C 5 -C 6 cycloalkyl, C 5 -C 8 cycloalkyl substituted with 1, 2, or 3 groups selected from C 1 -C 6 alkyl and C 2 -C 4 alkylidene,
C 5 -C 8 cycloalkenyl, C 5 -C 8 cycloalkenyl wherein the cycloalkenyl-ring is substituted with 1, 2, or 3 groups selected from C 1 -C 4 alkyl, C 2 -C 4 alkylidene, and C 3 -C 5 cycloalkyl,
(C 1 -C 3 )alkyl(C 5 -C 8 )cycloalkyl wherein the cycloalkyl-ring is optionally substituted with one group selected from —OH group and ═O group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups,
(C 1 -C 4 )alkyl(C 5 -C 6 )cyctoalkenyl wherein the cycloalkenyl-ring is optionally substituted one —OH group, and/or one or two ether group(s) and/or up to four C 1 -C 5 alkyl groups,
(C 2 -C 3 )alkenyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups,
C 6 -C 14 aryl,
C 6 -C 14 aryl wherein the aryl-ring is substituted with up to 3 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 11 wherein R 11 is independently selected from hydrogen and C 1 -C 4 alkyl,
(C 1 -C 3 )alkyl(C 6 -C 14 )aryl,
(C 1 -C 3 )alkyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 12 wherein R 12 is independently selected from hydrogen and C 1 -C 4 alkyl,
(C 2 -C 8 )alkenyl(C 6 -C 14 )aryl,
(C 2 -C 8 )alkenyl(C 6 -C 14 )aryl wherein the aryl-ring is substituted with up to 2 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 13 wherein R 13 is independently selected from hydrogen and C 1 -C 4 alkyl, and
bi-, tri, or tetracyclic hydrocarbon ring comprising C 8 -C 12 carbon atoms optionally substituted with up to 6 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 14 wherein R 14 is independently selected from hydrogen and C 1 -C 4 alkyl;
R 2 is selected from hydrogen, C 1 -C 5 alkyl, and C 2 -C 5 alkenyl;
or
R 1 and R 2 form together with the carbon atom to which they are attached
a) a 5 to 7 membered hydrocarbon ring(s), the ring(s) may optionally contain up to two ether groups, and/or the ring(s) may optionally be substituted with C 1 -C 5 alkyl groups
b) 2-(2-(4-methylcyclohex-3-en-1-yl)propyl)cyclopent-1-ylidene, or
c) a 14-17 membered hydrocarbon ring, the ring may optionally be substituted with a methyl group;
R 3 is hydrogen or methyl; and

X means a radical of formula (Ia)

wherein n is 0 or 1;
R 4 is hydrogen or methyl;
R 5 is hydrogen or methyl;
R 6 is selected from hydrogen, C 1 -C 5 alkyl, vinyl, hydroxys, methoxy or ethoxy; and
R 7 is selected from hydrogen, C 1 -C 5 alkyl, vinyl, hydroxyl, methoxy or ethoxy;
with the proviso that if one of R 6 and R 7 is hydroxyl then the other of R 6 and R 7 is selected from methoxy or ethoxy;
or
R 6 and R 7 form together with the carbon atoms to which they are attached a 5 or 6 membered ring containing up to two oxygen atoms, wherein the ring may optionally be substituted with up to 6 methyl groups;
with the proviso that
a) if n=0, R 1 is not a group selected from aryl and aryl substituted with an —OR 11 wherein R 11 is hydrogen or C 1 -C 4 alkyl; and
b) if R 3 is hydrogen and R 1 is selected from the group consisting of alkenyl, alkenylcycloalkenyl, alkenylaryl and cycloalkenyl in which no sp 3 -hybirdised C-atom is between C-1′ and the nearest C—C double bond of R 1 , then n=1.

2. A method according to claim 1 of generating a carbonyl compound of the formula

wherein n is 0 or 1;
R 3 is hydrogen or methyl;
R 4 is hydrogen or methyl;
R 5 is hydrogen or methyl;
R 6 is selected from hydrogen, C 1 -C 5 alkyl, vinyl, hydroxyl, methoxy or ethoxy; and
R 7 is selected from hydrogen, C 1 -C 5 alkyl, vinyl, hydroxyl, methoxy or ethoxy, with the proviso that if one of R 8 and R 7 is hydroxyl then the other of R 6 and R 7 is selected from methoxy or ethoxy;
or
R 6 and R 7 form together with the carbon atoms to which they are attached a 5 or 6 membered ring containing up to two oxygen atoms, wherein the ring may optionally be substituted with up to 6 methyl groups
characterized in that a compound of formula (I) is exposed to oxygen.

3. A method according to claim 2 wherein the carbonyl compound is selected from ethylvanilin, vanillin, 1-(naphthalen-2-yl)ethanone, acetophenone, 1,3-benzodioxole-5-carboxaldehyde, anisic aldehyde, veratric aldehyde, phenylacetic aldehyde, 4-methyl phenylacetaldehyde, benzaldehyde, 3-methyl-benzaldehyde, 1-(4-methoxyphenyl) ethanone, 4-(1-methylethyl)-benzenacetaldehyde, 2,4-(di-(1,1-dimethylethyl))-5-methoxy-benzaldehyde, 4-isopropyl-benzaldehyde, 1-(2,4-dimethyl phenyl)ethanone, 5,5,7,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone, 1-(5,6,7,8-tetrahydronaphthalen-2-yl) ethenone, 1-(1,2,3,3,6-hexamethyl-2,3-dihydro-1H-inden-5-yl)ethanone, 2-(4-isopropyl phenyl)propanal, 3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde, 2,3,3-trimethyl-2,3-dihydro-1H-inden-1-one, and mixtures thereof.

4. The method of claim 2 wherein the carbonyl compound is 4-methoxybenzaldehyde.

5. A method according to claim 1 of generating a fragrant aldehyde or ketone of the formula (II)

wherein
R 1 is selected from the group consisting of
C 5 -C 14 alkyl, C 5 -C 14 alkenyl,
C 5 -C 6 cycloalkyl, C 5 -C 8 cycloalkyl substituted with 1, 2, or 3 groups selected from
C 1 -C 6 alkyl and C 2 -C 4 alkylidene,
C 5 -C 8 cycloalkenyl, C 5 -C 8 cycloalkenyl wherein the cycloalkenyl-ring is substituted with 1, 2, or 3 groups selected from C 1 -C 4 alkyl, C 2 -C 4 alkylidene and C 3 -C 5 cycloalkyl,
(C 1 -C 3 )alkyl(C 5 -C 6 )cycloalkyl wherein the cycloalkyl-ring is optionally substituted with one group selected from —OH group and ═O group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups,
(C 1 -C 4 )alkyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups,
(C 2 -C 3 )alkenyl(C 5 -C 6 )cycloalkenyl wherein the cycloalkenyl-ring is optionally substituted with one —OH group, and/or one or two ether group(s), and/or up to four C 1 -C 5 alkyl groups,
C 6 -C 14 aryl,
C 6 -C 14 aryl wherein the aryl-ring is substituted with up to 3 groups selected from C 1 -C 4 alkyl, —O—CH 2 —O—, and —OR 11 wherein R 11 is independently selected

Assignees

• Baumgartner Corinne
• Flachsmann Felix
• Kraft Philip
• Givaudan Sa

Inventors

• Baumgartner Corinne
• Flachsmann Felix
• Kraft Philip

Classifications

• C07C15/44 Primary

  the hydrocarbon substituent containing a carbon-to-carbon double bond · CPC title

• C07C15/50

  polycyclic non-condensed · CPC title

• C11B9/0061

  compounds containing a six-membered aromatic ring not condensed with another ring · CPC title

• C07C47/575

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C11B9/0015 Primary

  containing oxygen as the only heteroatom · CPC title