85110-96-9Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS INTO THE ATTRACTING SUBSTANCES (SEX ATTRACTANTS) OF INSECTS. V. SYNTHESIS OF 3,11-DIMETHYL-2-NONACOSANONE, ONE OF THE COMPONENTS OF THE SEX PHEROMONE OF THE GERMAN COCKROACH Blattella germanica L. AND ITS ANALOG 11-METHYL-2-NONACOSANONE
Ishchenko, R. I.,Kovalev, B. G.,Rastegaeva, V. M.
, p. 2005 - 2007 (2007/10/02)
8-Oxo-6-nonenal was obtained by the reaction of adipaldehyde with acetylmethylenetriphenylphosphorane and was converted by acetalization into the unsaturated ketoacetal 1,1-diethoxy-6-nonen-8-one.The latter was converted by reaction with heptadecylmethylenetriphenylphosphorane into 1,1-diethoxy-8-methyl-6,8-hexacosadiene, the hydrogenation of which over platinum oxide led to the saturated 1,1-diethoxy-8-methylhexacosane.This acetal was hydrolyzed under acidic conditions to the corresponding aldehyde 8-methylhexacosanal, which was condensed with 3-diethylphosphono-2-butanone by the Horner reaction without further purification to 3,11-dimethyl-2-nonacosen-2-one.Hydrogenation of the latter over platinum oxide gave the final 3,11-dimethyl-2-nonacosanone, which is one of the components of the sex pheromone of the female German cockroach Blattella germanica L.The reaction of heptadecylmethylenetriphenylphosphorane at one carbonyl group of 2,11-dodecanedione gave 11-methyl-11-nonacosen-2-one, which was converted by hydrogenation over platinum oxide into the analog 11-methyl-2-nonacosanone.
