140459-83-2Relevant academic research and scientific papers
Studies on PPL catalyzed acetylation of 2-alkanols: Its application for the synthesis of 2-dodecanol and 2-tridecyl acetate, the pheromones of Crematogaster ants and Drosophila mulleri flies
Sharma, Anubha,Pawar, Archana S.,Chattopadhyay, Subrata
, p. 19 - 25 (1996)
Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.
(Z,Z)-4,7-tridecadien-(S)-2-YL acetate: Sex pheromone of Douglas-fir cone gall midge, Contarinia oregonensis
Gries, Regine,Khaskin, Grigori,Gries, Gerhard,Bennett, Robb G.,King, G.G. Skip,Morewood, Petra,Slessor, Keith N.,Morewood, W. Dean
, p. 2283 - 2297 (2007/10/03)
Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)-4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50μg) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.
Enantioselective Synthesis of (S)-(+)-2-Tridecanol Acetate, an Aggregation Pheromone Component of Drosophila mulleri
Enders, Dieter,Plant, Andrew
, p. 1241 - 1243 (2007/10/02)
The enantioselective synthesis of (S)-(+)-2-tridecanol acetate (ee = 93.5percent), an aggregation pheromone of Drosophila mulleri, is described.Key steps are the α-alkylation of the propiophenone SAMP-hydrazone (S)-2 (de 96percent) and the Baeyer-Villiger reaction of the ketone (S)-4.Key Words: (S)-(+)-2-Tridecanol acetate / SAMP-hydrazone / Baeyer-Villiger reaction / Pheromone, aggregation / Drosophila mulleri
