63408-51-5

Upstream product

• 56268-03-2 4-oxo-dodecanal 
• 13423-48-8 triphenylheptylphosphonium bromide 
• 59724-99-1 bromure d'heptyltriphenylphosphonium 
• 118377-34-7 (11E)-11-(methylthio)-7,11-nonadecadiene 
• 111-71-7 heptanal 
• 68820-32-6 (Z)-4-undecenal 
• 72855-91-5 (Z)-7-nonadecen-11-ol 
• 629-04-9 1-Bromoheptane 
• 21676-07-3 (Z)-undec-4-en-1-ol 
• 3314-49-6 octyllithium 
• 1901-45-7 1-hydroxy-dodecan-4-one 
• 35329-42-1 undec-1-en-3-ol 
• 629-05-0 n-octyne 
• 124-19-6 nonan-1-al 

Relevant academic research and scientific papers

Synthesis and biological testing of ester pheromone analogues for two fruitworm moths (Carposinidae)

A range of ester pheromone analogues for carposinid moths were synthesized and evaluated for biological activity. The analogues aimed to take advantage of the structural commonality of (7Z)-alken-11-ones found in this family. Analogues were tested on two pest species: Heterocrossa rubophaga and Coscinoptycha improbana. Two of the analogues, (2Z)-nonenyl nonanoate and (4Z)-heptyl undecenoate, elicited significant electroantennogram responses. Only (4Z)-heptyl undecenoate gave consistent responses with both moth species in single sensillum recording. Field trapping trials were conducted with these two analogues both individually and in combination with the pheromone of each of the two moth species. No attraction was observed to either of the analogues alone, by either moth species. However, when (4Z)-heptyl undecenoate was coupled with the pheromone, it produced a strong inhibitory effect in H. rubophaga, reducing male moth trap catch by over 95%. No inhibitory effect on male moth trap catch was observed in C. improbana.

A Convenient Synthesis of the Peach Fruit Moth Carposina Niponensis Walk. and of the Douglas Fir Tussock Moth Orgya Pseudotsugata Mc.D. Sex Pheromones and Analogs

The (Z)- and (E)-isomers of 7-alken-11-ones with chain lengths of 19, 21 and 23 carbon atoms were synthesized.A procedure based on the reaction of alkenylcopper reagents with vinylketones has been elaborated.

Chemistry of Cyclic Phosphorus Compounds. 3. Synthesis of Pheromones Having an γ,δ-Unsaturated Ketone System from 1,1-Diphenylphospholanium Perchlorate

1,1-Diphenylphospholanium perchlorate (1) was converted into the sex pheromones 5a,b of the Japanese female peach fruit moth by use of use tandem Wittig reactions.The ylide of 1 formed with potassium tert-butoxide reacted with heptanal to give Z phosphine oxide 2 with stereoselectivity.The reaction of the anion of 2 with dimethyl disulfide followed by the Horner-Wittig reaction with nonanal or octanal gave the corresponding diene derivatives 4a,b.Hydrolysis of 4a,b afforded the desired the Z γ,δ-unsaturated ketones 5a,b.On the other hand, the conversion of 9, which was derived from methylthio-substituted compound 6, gave an E and Z isomeric mixture of 5b (4:5).

New Synthesis of (Z)-7-Nonadecen-11-one and (Z)-7-Eicosan-11-one: Sex Pheromone Components of Peach Fruit Moth

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.)

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.