136376-56-2Relevant articles and documents
Biocatalytic synthesis of (S)-2-tridecanyl acetate and (S)-2-pentadecanyl acetate, aggregation pheromone components of Drosophila mulleri and D.busckii, by enantioselective hydrolysis with lipase
Kamezawa,Tachibana,Ohtani,Naoshima
, p. 1057 - 1061 (1994)
-
Stabilization of long-chain intermediates in solution. octyl radicals and cations
Teodorovi?, Aleksandar V.,Badjuk, Dalibor M.,Stevanovi?, Nenad,Pavlovi?, Radoslav Z.
, p. 19 - 24 (2013/06/26)
The rearrangements of 1-octyl, 1-decyl and 1-tridecyl intermediates obtained from thermal lead(IV) acetate (LTA) decarboxylation of nonanoic, undecanoic and tetradecanoic acid were investigated experimentally through analysis and distribution of the products. The relationships between 1,5-, 1,6- and possibly existing 1,7-homolytic hydrogen transfer in 1-octyl-radical, as well as successive 1,2-hydride shift in corresponding cation have been computed via Monte-Carlo method. Taking into account that ratios of 1,5-/1,6-homolytic rearrangements in 1-octyl- and 1-tridecyl radical are approximately the same, the simulation shows very low involvement of 1,7-hydrogen rearrangement (1,5-/1,6-/1,7-hydrogen rearrangement = 85:31:1) in 1-octyl radical.
(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.
Synthesis of derivatives of (S)-2-alkanols, components of pheromones of Drosophila mulleri and Rhyzopertha dominica, from (S)-(+)-3,7-dimethylocta-1,6-diene
Ishmuratov,Kharisov,Botsman,Zorin,Tolstikov
, p. 1899 - 1901 (2007/10/03)
Effective routes for the synthesis of (S)-2-acetoxytridecane, the sex pheromone of the fruit fly Drosophila mulleri, and (S)-1-methylbutyl 2-methyl- and 2,4-dimethylpent-2E-enoates, components of the aggregation pheromone of the lesser grain borer Rhyzopertha dominica, were developed on the basis of (S)-4-methylhex-5-en-1-yl tosylate accessible from (S)-(+)-dihydromyrcene.