Polyalkylbicylic derivatives

Details Polyalkylbicylic derivatives Polyalkylbicylic derivatives

2001-05-17

2003-10-14

Warden, Jill (Department: 1743)

Perfume compositions

Perfume compositions

Ring containing active ingredient

C512S008000, C512S009000, C512S011000, C512S013000, C512S015000, C512S016000, C512S017000, C512S022000, C512S023000, C512S025000, C512S026000, C549S200000, C549S330000, C549S331000, C549S356000, C549S381000, C549S385000, C568S300000, C568S303000, C568S376000, C568S377000, C568S379000

Reexamination Certificate

active

06632788

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to new chemical entities and the incorporation and use of the new chemical entities as fragrance chemicals.
BACKGROUND OF THE INVENTION
U.S. Pat. Nos. 5,227,367; 5,733,866; and 5,665,698 hereby incorporated by reference as iset forth in their entirety disclose polycyclic chemicals that are suitable for use as fragrance chemicals. Those with skill in the art appreciate how differences in the chemical structure of the molecule can result in significant differences in the odor, notes and characteristics of a molecule. These variations and the ongoing need to discover and use the new chemicals in the development of new fragrances allows perfumers to apply the new compounds in creating new fragrances.
SUMMARY OF THE INVENTION
The present invention provides novel chemicals, and the use of the chemicals to enhance the fragrance of perfumes, toilet waters, colognes, personal products and the like. In addition, the present invention is directed to the use of the novel chemicals to enhance fragrance in perfumes, toilet waters, colognes, personal products and the like.
More specifically, the present invention is directed to the novel compounds, represented by the structure of Formula I set forth below:
where A is
B is
or A and B together form the ring structure
and X, R′ and R are independently H and CH
3
and m=0 or 1.
Another embodiment of the invention is a method for enhancing a fragrance by incorporating an olfactory acceptable amount of the compound provided above.
These and other embodiments of the present invention will be apparent by reading the following specification.
DETAILED DESCRIPTION OF THE INVENTION
The novel compounds of the present invention are more fully described by the following structures:
where X, A, and B are as described above.
Those with skill in the art will appreciate that the dotted line represents a single or double bond. In a preferred embodiment the molecule does not contain a double bond. In a highly preferred embodiment the molecules contain the ring structure without the double bond and m=0. These molecules are represented by the following structure:
where A, B and X have the definition set forth above. In a preferred embodiment of the invention the compounds have the following structure
Most preferably M=0 and R and R′ are independently selected from H and CH
3
.
Highly preferred embodiments of the invention are the following compounds wherein the substituents have the following values when applied to the compound of Formula I:
COMPOUND
A, B, X, M. VALUES
4,10,10,11,12,12-
A and B together
(intentionally
X is
M = 0;
hexamethyl-3-
form the 5
left blank)
CH
3
and the
oxatricyclo
member ring
rings
[7.3.0.0,<2,6>]
structure and R is
are
dodecane
H and R′ is CH
3
satur-
ated
4,4,10,10,11,12,
A and B together
(intentionally
X is
M = 0;
12-heptamethyl-
form the 5
left blank)
CH
3
and the
3-oxatricyclo
member ring
rings
[7.3.0.0,<2,6>]
structure and R is
are
dodecane
CH
3
and R′ is CH
3
satur-
ated
1,1,2,3,3-penta-
A is = 0
B is the ketone
X is
M = 0;
methyl-5-prop-2-
structure and R
CH
3
and the
enyl-2,3,5,6,7-
is H
double
pentahydroinden-
bond is
4-one
present
1,1,2,3,3-penta-
A is = 0
B is the ketone
X is
M = 0;
methyl-5-(2-
structure and R
CH
3
and the
methylprop-2-
is CH
3
double
enyl)-2,3,5,6,7-
bond is
pentahydroinden-
present
4-one
The novel compounds of the present invention are prepared by one of several reaction sequences set forth below. The compounds of Examples 1, 2, 3, 8, 9, 10, 12, 13, and 14, set forth below, were prepared by the sequence:
The reaction sequence set forth above is summarized by the following reactions. The first reaction is a three (3) carbon addition via allyl alcohol Claisen rearrangement or carbon alkylation with methallyl chloride. This reaction (Claisen rearrangement) is typically conducted at a temperature of from about 150 to about 250° C. In a preferred embodiment the reaction is catalyzed using an acid catalyst, preferably methanesulfonic acid or para toluenesulfonic acid. The carbon addition reaction is then followed by an aluminum hydride ketone reduction reaction. The ketone is reduced to form the corresponding alcohol. The final reaction set forth above is an acid catalyzed ether formation that is conducted at a temperature of from about 70 to about 130° C. This reaction is usually conducted in a solvent such as xylene or toluene with toluene being the preferred solvent.
The compounds of Examples 5-7 were prepared by the following general sequence:
The first reaction is a carbon alkylation employing either allyl chloride or methallyl chloride depending if the desired R group is H or CH
3
. This reaction is typically conducted at a temperature of from about 23 to about 100° C. The reaction is usually conducted with a base catalyst employing sodium methoxide or sodium hydroxide. The next reaction is a thermal Claisen rearrangement conducted at a temperature of from about 170 to about 250° C. The third reaction is an acid catalyzed ether formation employing similar temperatures and catalysts as described above, followed by a catalytic hydrogenation employing rhodium or platinum as a catalyst.
The compounds of Examples 4 and 11 are prepared by the sequence:
wherein the reaction is a three (3) carbon addition via allyl alcohol Claisan rearrangement or carbon alkylation with methallyl chloride using the conditions and catalysts described above.
The starting materials when M=0 for the above described reaction can be found in U.S. Pat. Nos. 5,227,367, 5,733,866 and 5,665,698. Similarly, the starting materials for the above materials when M=1 can be found in U.S. Pat. No. 3,927,083, hereby incorporated by reference, German patent 2330648 and Japanese patent 09249584.
Those with skill in the art will recognize that the compounds of the present invention have several chiral centers, thereby providing numerous isomers of the claimed compounds. As used herein the compounds described herein include the isomeric mixtures of the compounds as well as those isomers that may be separated using techniques known to those with skill in the art. Suitable techniques include chromatography, particlularly gel chromatography.
The optical isomers for the compound 4,10,10,11,12,12-hexamethyl-3-oxatricyclo[7.3.0.0<2,6>]dodecane are provided in the following table. One with skill in the art would be able to formulate fragrance compositions using one or more or the following isomers and mixtures of the isomers:
(1R, 2R, 4R, 6R, 9R, 11R)-Z
(1S, 2S, 4R, 6R, 9S, 11S)-Z
(1S, 2R, 4R, 6R, 9S, 11S)-Z
(1R, 2R, 4R, 6R, 9R, 11S)-Z
(1R, 2S, 4R, 6S, 9R, 11S)-Z
(1R, 2R, 4R, 6S, 9S, 11S)-Z
(1R, 2R, 4R, 6R, 9S, 11R)-Z
(1S, 2S, 4S, 6R, 9S, 11R)-Z
(1S, 2R, 4R, 6R, 9R, 11S)-Z
(1R, 2R, 4R, 6S, 9R, 11R)-Z
(1S, 2S, 4R, 6S, 9R, 11S)-Z
(1S, 2S, 4S, 6S, 9S, 11S)-Z
(1R, 2R, 4S, 6R, 9R, 11R)-Z
(1S, 2R, 4S, 6R, 9S, 11S)-Z
(1S, 2R, 4S, 6S, 9R, 11S)-Z
(1R, 2S, 4R, 6R, 9R, 11R)-Z
(1R, 2S, 4R, 6S, 9S, 11S)-Z
(1S, 2S, 4R, 6R, 9R, 11S)-Z
(1S, 2R, 4R, 6R, 9R, 11R)-Z
(1S, 2S, 4R, 6R, 9S, 11R)-Z
(1S, 2S, 4S, 6R, 9R, 11R)-Z
(1R, 2R, 4R, 6R, 9S, 11S)-Z
(1S, 2R, 4R, 6S, 9S, 11R)-Z
(1S, 2S, 4R, 6S, 9S, 11R)-Z
(1R, 2R, 4R, 6S, 9S, 11R)-Z
(1S, 2R, 4R, 6S, 9R, 11S)-Z
(1R, 2R, 4S, 6S, 9S, 11S)-Z
(1R, 2R, 4S, 6S, 9R, 11R)-Z
(1R, 2R, 4S, 6R, 9S, 11S)-Z
(1S, 2R, 4S, 6R, 9S, 11S)-Z
(1R, 2S, 4S, 6R, 9R, 11R)-Z
(1R, 2R, 4S, 6S, 9R, 11S)-Z
(1S, 2R, 4S, 6S, 9R, 11S)-Z
(1S, 2S, 4R, 6R, 9R, 11R)-Z
(1R, 2S, 4R, 6R, 9S, 11R)-Z
(1S, 2S, 4R, 6R, 9S, 11R)-Z
(1R, 2R, 4R, 6S, 9S, 11S)-Z
(1R, 2S, 4R, 6S, 9R, 11R)-Z
(1S, 2R, 4R, 6S, 9S, 11S)-Z
(1R, 2R, 4S, 6S, 9S, 11R)-Z
(1R, 2R, 4S, 6R, 9R, 11S)-Z
(1S, 2S, 4R, 6R, 9S, 11S)-Z
(1R, 2S, 4S, 6S, 9R, 11R)-Z
(1R, 2S, 4R, 6R, 9S, 11R)-Z
(1S, 2S, 4S, 6R, 9R, 11S)-Z
(1S, 2S, 4S, 6R, 9R, 11R)-Z
(1R, 2R, 4S, 6S, 9R, 11R)-Z
(1S, 2S, 4S, 6S, 9R, 11R)-Z
(1R, 2S, 4S, 6S, 9S, 11R)-Z
(1S, 2R, 4S, 6R, 9S, 11R)-Z
(1R, 2S, 4S, 6S, 9S, 11S)-Z
(1R, 2R, 4R, 6S, 9R, 11

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