Compositions – Electrically conductive or emissive compositions – Metal compound containing
Patent
1982-11-09
1984-07-03
Reamer, James H.
Compositions
Electrically conductive or emissive compositions
Metal compound containing
568376, 568377, 568379, 568378, C07C 49537, A61K 746
Patent
active
044578628
DESCRIPTION:
BRIEF SUMMARY
The invention is concerned with novel odorant substances. These are compounds of the formula ##STR3## wherein R signifies an aliphatic group of the formula ##STR4## in which R.sup.1 is C.sub.1-4 -alkyl, C.sub.1-4 -alkylidene or C.sub.2-4 -alkenyl and the sum of the carbon atoms in these groups is 2-5, m and n are 0 or 1, p is 1, 2 or 3 and the dotted lines represent one or two optional double bonds.
The alkyl, alkenyl or alkylidene groups denoted by R.sup.1 can be straight-chain or branched-chain. Examples of alkyl groups are methyl, ethyl, propyl, isopropyl, n-butyl, sec.-butyl and tert.-butyl. Vinyl, propenyl, isopropenyl and butenyl are examples of alkenyl groups. Examples of alkylidene groups are methylidene, ethylidene, propylidene, isopropylidene and butylidene.
R.sup.1 is preferably methyl. p is preferably 3. When p is 2 or 3 the groups R.sup.1 can be the same or different. m is preferably the same as n; m and n both being 1 are especially preferred.
R preferably represents one of the following groups: ##STR5##
The first of these groups is particularly preferred.
Formula I is also intended to embrace the stereoisomers which occur as a result of the asymmetric centres, the double-bond isomers and the corresponding enol forms of the diketones of formula I. The enol forms of the 1,3-diketones are: ##STR6##
The present invention is also concerned with a process for the manufacture of the compounds of formula I.
This process comprises reacting an enamine of cyclopentanone with an acid halide of the formula ##STR7## wherein R has the significance given earlier and X represents halogen.
As the acid halides there come into consideration especially the chloride, bromide and iodide, with the chloride being preferred.
The manufacture of the diketones of formula I can therefore be carried out according to the known methodology of enamine acylation; see, for example, G. Stork, A. Brizzolara, H. Landesmann, J. Szmuskovicz and R. Terrel in J. Amer. Chem. Soc. 85, 207 (1963).
As the enamine-former there can be used, for example, the following secondary amines:
Aliphatic secondary amines such as dialkylamines (e.g. diethylamine) or cyclic secondary amines such as, for example, morpholine, piperidine or pyrrolidine. Morpholine is preferred.
The reaction of the enamine with the halide of formula II is conveniently carried out in a solvent and with the exclusion of air and moisture. Suitable solvents are anhydrous solvents such as, for example, methylene chloride, chloroform, dioxan, benzene, toluene, dimethyl formamide etc; methylene chloride and chloroform are preferred.
The molar ratio of enamine to halide is conveniently approximately 1:1, but the enamine can also be used in excess (e.g. in a two-fold amount or even more). However, the addition of any amine (e.g. triethylamine) can replace the excess of the enamine necessary to neutralize the acid formed.
The reaction is conveniently carried out at a temperature between 0.degree. C. and the reflux temperature of the reaction mixture, preferably at about 40.degree. C. For example, the mixture is left for several hours at this temperature. Thereupon, the mixture is cooled, conveniently to room temperature, and then an acid (e.g. hydrochloric acid) is added thereto. The amine-cleavage can then be achieved by renewed heating (e.g. at reflux temperature).
The isolation of the reaction product can be carried out according to methods known per se. For example, the reaction product is taken up in an organic solvent and the organic solution is washed firstly with dilute hydrochloric acid such as a 10% HCl solution. After washing neutral and drying, the crude product can be purified by usual methods such as, for example, adsorption chromatography and/or distillation.
The compounds of formula I have particular organoleptic properties, on the basis of which they are excellently suited as odorant substances.
The invention is accordingly also concerned with the use of the compounds of formula I as odorant substances.
The compounds of formula I possess, in particular, woody-anima
REFERENCES:
patent: 3578686 (1971-05-01), Tuliar et al.
patent: 3845133 (1974-10-01), Cohen
Baudin Josiane
Gonzenbach Hans U.
Givaudan Corporation
Reamer James H.
Tavares Robert F.
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