90687-15-3Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS INTO INSECT ATTRACTANTS (SEX ATTRACTANTS). VI. SYNTHESIS OF cis-7-NONADECEN-11-ONE AND cis-7-EICOSEN-11-ONE - COMPONENTS OF THE SEX PHEROMONE OF THE PEACH FRUIT MOTH (Carposina niponensis W.)
Sorochinskaya, A. M.,Ishchenko, R. I.,Kovalev, B. G.
, p. 237 - 241 (2007/10/02)
A new synthesis is described for cis-7-nonadecen-11-one and cis-7-eicosen-11-one, components of the sex pheromone of the peach fruit moth Carposina niponensis W.Ethoxycarbonylation of 1-(2-tetrahydropyranyloxy)-4-pentanone gave 1-(2-tetrahydropyranyloxy)-5-ethoxycarbonyl-4-pentanone, which was converted into 1-hydroxy-4-tridecanone and 1-hydroxy-4-dodecanone respectively by alkylation with octyl and heptyl bromide followed by ketone cleavage and removal of the tetrahydropyranyl protection.By oxidation of the two ketols with pyridinium chlorochromate the followingaldehydes were obtained: 4-oxotridecanal and 4-oxododecanal.By reaction with hexamethylenetriphenylphosphorane at the aldehyde group the keto aldehydes were converted into unsaturated ketones - components of the sex pheromone.
