Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2001-10-29
2003-11-11
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
Reexamination Certificate
active
06645932
ABSTRACT:
BACKGROUND OF THE INVENTION
The invention relates to new chemical compounds useful as perfumes or as components of perfumes. More specifically it relates to alkyl-substituted 2-acylindenes and isomeric mixtures thereof.
There is a continuing search for materials having useful perfumery fragrance characteristics. These materials are sought either as replacements for naturally occurring compounds or as totally new scents or odour notes in their own right. For practicability reasons such materials should possess other favorable properties e.g. substantivity and stability in applications, all in addition to their useful odour notes.
SUMMARY OF THE INVENTION
It is the object of the present invention to provide a series of novel and practicable synthetic materials or isomeric mixtures thereof, being alkyl-substituted indenes comprising an acyl moiety in the 2-position, and possessing very useful and strong odours with woody, straw- and hay-like notes. These novel indenes are represented by the generic Formula I
wherein R
1
, R
2
each represent a lower alkyl group and R
3
, R
4
, R
5
, R
6
, R
7
and R
8
each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
or R
8
together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, and wherein the total number of carbon atoms in formula I is twenty two or less, with the proviso that R
1
and R
2
together do not represent a tetramethylene moiety if R
3
, R
4
, R
5
, R
6
, R
7
and R
8
all represent hydrogen, and with the proviso that R
8
does not represent hydrogen if R
1
, R
2
, R
4
, R
5
, R
6
, R
7
and R
8
all represent a methyl group.
In the present context the term “lower alkyl” indicates a straight or branched alkyl group or a cycloalkyl or alkyl-substituted cycloalkyl group, an of 1-6 carbon atoms.
It will be apparent that the novel indenes can exist in a variety of positional, stereoisomeric and enantiomeric forms and it is intended that these be included within the structural formulae.
In the compounds of the invention represented by the generic Formula I. R
1
, R
2
each represent a lower alkyl group and R
3
, R
4
, R
5
, R
6
, R
7
and R
8
each represent hydrogen or a lower alkyl group, or two substituents chosen from R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
or R
8
together may represent a di-, tri- or tetra- or pentamethylene moiety or a lower alkyl-substituted di-, tri- or tetra- or pentamethylene moiety and the remaining substituents represent hydrogen or a lower alkyl group, with the proviso that R
1
and R
2
together do not represent a tetramethylene moiety if R
3
, R
4
, R
5
, R
6
, R
7
and R
8
all represent hydrogen, and with the proviso that R
3
does not represent hydrogen if R
1
, R
2
, R
4
, R
5
, R
6
, R
7
and R
8
all represent a methyl group.
In a preferred embodiment of the invention R
3
represents an alkyl group of four carbon atoms or less. In a more preferred embodiment R
8
is a methyl group. In an alternative embodiment R
1
, R
2
are selected from methyl and ethyl groups and R
4
, R
5
, R
6
, R
7
and R
8
each are selected from hydrogen, methyl and ethyl groups with a total number of carbon atoms in R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and R
8
together of eight or less. According to a specially preferred embodiment R
1
, R
2
and R
4
represent each a methyl group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The compounds of the invention are new. Only a few, simple alkyl-substituted 2-acylindenes are known, see for example Chem. Abstr. 114:121685; 105:115070; 93:238411; 107:175558; 90:54197; 84:121530; 83:131170; 117:131346; 110:94192; 109:54897; 107:217199; 107:40061; 105:226283; 95:23687; 79:136870 and 79:115338. These compounds appear to be mainly of scientific interest or are useful as intermediates for veterinary sedative antagonists or are rated odorless. None of them relates to possible uses as perfume or as component of perfumes.
In British patent application 2233645 the preparation and the use for the improvement of the fragrance of perfume compositions of 2-acylindanes are disclosed. Although these indanes are said to have no particularly powerful fragrance themselves, they would have an extra “harmonizing” and “rounding off” effect when added to other odoriferous materials in very low concentrations. The method of preparation of the disclosed indanes is mainly of academic interest and involves many laborious and impractical steps with low overall yields and would not be suitable for cost-effective industrial production.
For the chemist skilled in the art it will be apparent that the structural and three-dimensional conformation of the novel 2-acylindenes of the present invention differs significantly from the 2-acylindanes disclosed in British patent application 2233645. For the fragrance chemist skilled in the art it is understood that the three-dimensional position of the osmopheric group, being the ketone moiety of the acyl group, relative to the plain of the backbone of the molecule is decisive for the odour characteristic of the molecule. In 2-acylindanes the carbon atom in the 2-position is using four sp
3
-hybridized orbitals to form tetrahedral bonds with the four atoms to which it is connected in a three-dimensional configuration. Consequently the position of the acyl moiety is out of the plain of the cyclic skeleton of the molecule. This is significantly different from the situation in 2-acylindenes of the present invention, wherein the carbon atom in the 2-position uses three sp
2
-hybridized orbitals to form trigonal bonds with the three atoms to which it is connected, in a two-dimensional configuration. Therefor, in the case 2-acylindenes the position of the acyl moiety is in the plain of the cyclic skeleton of the molecule, which for fragrance chemists skilled in the art makes the odour characteristics unpredictable and unexpected over the prior art.
The novel indenes of the invention can be prepared by methods known to the art for analogous compounds e.g. as described in the literature references herein above. Of the methods known, the preferred method for each compound of the invention may be different and will depend on considerations of economics, availability of starting materials, byproduct formation, technical feasibility, safety, organoleptic grade produced, and the like, which parameters, circumstances and conditions may be subject to change over time, location, facility, etc.
A preferred chemical method in this context involves selective formylation or acylation of the alkene moiety of indenes of the generic Formula II,
wherein the provisos for R
1
, R
2
, R
4
, R
5
, R
6
, R
7
and R
8
are the same as defined herein above for Formula I, by general methods known to the art e.g. as set forth in J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th edition, J. Wiley & Sons, N.Y., 1992, pp. 598-600, and references cited therein, and in G. A. Olah, Friedel Crafts and Related Reactions, Interscience Publishers, 1964, vol. III, part 2, pp. 1033-1071, and references cited therein. The starting indenes of Formula II can be prepared by methods known to the art e.g. as set forth in the references cited in CA 95:42765; CA 95:24598; CA 93:71383; CA 74:87684; CA 54:24584; CA 47:2169; CA 44:1056 and CA 43:5762.
An alternative preferred chemical method of preparation of the compounds of the invention involves conversion under Friedel Crafts acylation conditions, generally known to the art, e.g. as set forth in the references cited herein above, of indanes represented by the generic Formula III, wherein the provisos for R
1
, R
2
, R
4
, R
5
, R
6
, R
7
and R
8
are the same as defined
herein above for Formula I, and wherein R
9
, R
10
, R
11
, R
12
, and R
13
each represent hydrogen or a lower alkyl group or wherein two substituents chosen from R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
1
Lenselink Willem
van Manen Anton Pieter J.
Cole Monique T.
PFW Aroma Chemical B.V.
Warden Jill
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