63408-44-6Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS IN THE REGION OF INSECT ATTRACTANTS (SEX ATTRACTANTS). IX. 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.,Kovalev, B. G.,Avdeeva, L. A.
, p. 277 - 283 (2007/10/02)
The 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., from furfural is described.
New Synthesis of (Z)-7-Nonadecen-11-one and (Z)-7-Eicosan-11-one: Sex Pheromone Components of Peach Fruit Moth
Dasaradhi, Lakkaraju,Rao, Jagadishwar,Bhalerao, Uday T.
, p. 167 - 168 (2007/10/02)
Reaction of allyl bromide and aldehyde (3) and (4) in the presence of zinc and aqueous ammonium chloride leads to the corresponding homoallylic alcohols (5) and (6) which on hydroboration followed by PCC oxidation give the key intermediates, the ketoaldehydes (9) and (10), respectively in good yields.Ketoaldehydes (9) and (10) on Wittig reaction with heptyltriphenylphosphonium bromide yield the title ketonic pheromones (1) and (2) respectively.
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.
