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Compound - me-E2,4,5-tetradecatrienoate


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Methyl (E)-2,4,5-tetradecatrienoate
Methyl (E)-2,4,5-tetradecatrienoate

Formula: C15H24O2 
MW: 236.35 

[MS]  [ NMR ]  [Behavioural function]  [Chemdraw

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Reference(s) for synthesis of Methyl (E)-2,4,5-tetradecatrienoate

Baudouy, R., and Gore, J. 1974. New synthesis of a pheromone with a vinyl allenic linkage. Synthesis. 8:573-574.
Descoins, C., Henrick, C.A., and Siddall, J.B. 1972. Synthesis of a presumed sex attractant of the dried bean beetle. Tetrahedron Lett. 13:3777-3780.
Franck-Neumann, M., and Brion, F. 1979. Synthesis of allenes from electrophilic acetylenes via novel allenemanganese complexes. Angew. Chem. Int. Ed. Engl. 18:688-689.
Fujisawa, T., Iida, S., and Sato, T. 1984. A convenient synthesis of allenes by the reaction of propargyl alcohols with Grignard reagents using 1-chloro-2-methyl-N,N-tetramethylenepropenylamine. Tetrahedron Lett. 25:4007-4010.
Henrick, C.A. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889.
Hosomi, A., Saito, M., and Sakurai, H. 1979. 2-trimethylsilylmethyl-1,3-butadiene as a novel reagent for isoprenylation. New access to ipsenol and ipsdienol, pheromones of Ips paraconfusus. Tetrahedron Lett. 20:429-432.
Khrimyan, A.P., and Badanyan, S.O. 1981. Reactions of unsaturated compounds. LXXI. New approach to the synthesis of trans-2,4,5-tetradecatrien-1-ol, the precursor of the pheromone of the parasitic bean weevil. Arm. Khim. Zhur. 34:254.
Kleijn, H., Westmijze, H., Kruithof, K., and Vermeer, P. 1979. Organocuprate induced allylic versus propargylic 1,3substitution in sulfinates and sulfonates derived from 3-hydroxy-1-penten-4-ynes. Improved synthesis of a precursor for the presumed sex attractant of Acanthoscelides obtectus. Rec. J. Roy. Neth. Chem. Soc. 98:27.
Kocienski, P.J, Cernigliaro, G., and Feldstein, G. 1977. A synthesis of ()-methyl n-tetradeca-trans-2,4,5-trienoate, an allenic ester produced by the male dried bean beetle Acanthoscelides obtectus (Say). J. Org. Chem. 42:353-355.
Landor, P.D., Landor, S.R., and Mukasa, J. 1971. Synthesis of ()-methyl tetradeca-trans-2,4,5-trienoate the allenic sex pheromone produced by the male dried bean beetle. J. Chem. Soc. Chem. Comm. 24:1638-1639.
Le Doussal, B., Gorgues, A., and Le Coq, A. 1985. Reduction d'acetals gamma-bromo alpha-acetyleniques par les sels chrorneux: acces aus acetals et aldehydes alpha-alleniques. Tetrahedron Lett. 26:51-52.
Le Doussal, B., Le Coq, A., Gorgues, A., and Meyer, A. 1983. Reduction par les ions chromeux de derives bromopropargyliques en composes alleniques. Application a la synthese de la pheromone de la bruche du Haricot sec. Tetrahedron. 39:2185-2192.
Michelot, D., and Linstrumelle, G. 1976. Cuprates alleniques I: preparations et reactions. Synthese stereoselective de la pheromone de la bruche parasite du Haricot. Tetrahedron Lett. 4:275-276.
Mori, K., Nukada, T., and Ebata, T. 1981. Synthesis of optically active forms of methyl (E)-2,4,5-tetradecatrienoate, the pheromone of the male dried bean beetle. Tetrahedron. 37:1343-1347.
Pirkle, W.H., and Boeder, C.W. 1978. Synthesis and absolute configuration of (-) methyl (E)-2,4,5-tetradecatrienoate, the sex attractant of the male dried bean weevil. J. Org. Chem. 43:2091-2093.
Rodini, D.J., and Snider, B.B. 1980. Dimethylaluminum halide induced reactions of formaldehyde with alkynes. Synthesis of alpha-allenic alcohols and z-3-chloroallylic alcohols. Tetrahedron Lett. 21:3857-3860.
Westmijze, H., Ruitenberg, K., Meijer, J., and Vermeer, P. 1982. Stereospecific synthesis of vinylstannanes using triphenylstannylcopper (I) species. Preparation of the cis-isomer of the presumed sex attractant of Acanthoscelides obtectus. Tetrahedron Lett. 23:2797-2798.

Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <>.
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