Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1993-08-05
1994-07-12
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568826, 568827, 568832, 512215, C07C 3305, C07C 3316, C07C 31137, A61K 746
Patent
active
053290526
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND
The invention relates to novel odorants derived from formylpinane.
DETAILED DESCRIPTION
In particular, these are compounds of the general formula ##STR2## in which R represents H or C.sub.1 -C.sub.4 alkyl, for example methyl, ethyl, propyl, butyl etc., preferably methyl or ethyl, n represents 0 or 1 and the notation represents a single or double bond.
The general formula represents both pure isomers and mixtures of configurational (carbons 2, 1', 3', 4', 5') and geometric double bond of the side chain isomers. In the general formula the configuration of the pinanyl radical depends on that of the formylpinane used in the synthesis.
These novel compounds are prepared by reducing a compound of the formula ##STR3##
The route to these novel compounds I starting from the compounds II is represented in Schemes 1 and 2.
These Schemes also show the preferred routes to the compounds II. ##STR4##
One possible route to the compounds I is represented in Schemes 1 and 2 and comprises one of the following conversions: from e.g. 3-bromo-2-methylpropanal, protected in the dioxolane form, and from a phosphine, e.g. PPh.sub.3 ; "C.dbd.C" double bond.
The reactions and separation techniques are known per se, namely: organic bases; using metal hydrides, e.g. LiAlH.sub.4, NaBH.sub.4 ; see also process e); palladium on charcoal, carried out at atmospheric pressure (.fwdarw.d)) or above, e.g. up to approximately 30 atm. or more (.fwdarw.b)); another physico-chemical method, e.g. fractionation under reduced pressure; with a strong base, e.g. butyllithium, in a solvent, for example an ether such as THF; acid, accompanied by the migration of a carbon-carbon double bond ending in an .alpha.,.beta.-unsaturated system; the solvent is, for example, an ether, preferably THF.
The details of these methods are given in the Examples. It will be understood that modifications concerning the reactants and the reaction conditions are possible and are an integral part of the invention.
The compounds of formula I can be isolated by extracting the reaction mixture (separated from the catalyst or hydrolyzed), with an organic solvent, preferably ethyl ether, methylene chloride or toluene and the like.
The residue can be purified by fractional distillation or flash chromatography.
Formylpinane can be efficaciously prepared starting from .alpha.-pinene. The enantiomerically pure forms of this compound can be obtained depending on whether (-)-.alpha.-pinene or (+)-.alpha.-pinene is used as the starting material (DE 2,404,306 of 31.7.1975) and can be used individually or as a mixture: ##STR5##
It has been found that the compounds I have advantageous olfactory properties and can be used as perfume ingredients. This use in perfumery is also an object of the invention.
The olfactory notes of the aforementioned compounds are woody with an amber and sandalwood tonality.
The present invention also relates to the use of the said compounds, separately or as a mixture, as perfume ingredients for the preparation of perfumes or scented products.
These derivatives of formylpinanes have a woody note with an amber tonality which is extremely advantageous for use in perfumery. As modern perfumery imposes all kinds of constraints, especially as regards eliminating the use of amber notes of animal origin, such as ambergris, it is very important to search for synthetic products with a similar effect in harmony with other families of notes which are widely used, such as the woody ones.
This is the case with these derivatives which combine, according to the individual structure, a more or less woody or amber effect.
Their olfactory value makes it possible for them to harmonize with the majority of natural or synthetic products already widely used in compositions principally for the middle and bottom notes, since these derivatives are endowed with an excellent tenacity (several days on a "blotter" and in various bases).
These derivatives harmonize particularly well with all the floral notes and principally jasmin, rose, narcissus, iris and ylang-ylang. They al
REFERENCES:
patent: 4081477 (1978-03-01), Hoffmann et al.
patent: 4424378 (1984-01-01), Mookherjee et al.
patent: 4428387 (1984-01-01), Mookherjee et al.
Auger Bernard
Bajgrowicz Jerzy A.
Giraudi Edouard
Givaudan-Roure Corporation
Gould George M.
Johnston George W.
Lone Werren B.
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