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Compound - E7Z9-12Ac


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(E,Z)-7,9-Dodecadienyl acetate
(E,Z)-7,9-Dodecadienyl acetate

Formula: C14H24O2 
CAS#: 54364-62-4 
MW: 224.34 

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

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Reference(s) for synthesis of (E,Z)-7,9-Dodecadienyl acetate

Bestmann, H.J., Suess, J., and Vostrowsky, O. 1979. Pheromone XXVI. Synthese der sexuallockstoffe (E)-7,(Z)-9-dodecadienylacetat, (E)-9,11-dodecadienylacetat und (Z)-9, (E)-11-tetradecadienylacetat. Tetrahedron Lett. 20:2467-2470.
Cassani, G., Massardo, P., and Piccardi, P. 1979. New simple synthesis of internal conjugated (Z)-enynes. Tetrahedron Lett. 20:633-634.
Cassani, G., Massardo, P., and Piccardi, P. 1980. Synthesis of Lobesia botrana and Spodoptera littoralis natural sex attractants. Tetrahedron Lett. 21:3497-3498.
Cassani, G., Massardo, P., and Piccardi, P. 1983. A stereospecific synthesis of conjugated (E,Z)- and (E,E)-alkadienes by the palladium-catalyzed reaction of (E)-1-alkenylboronic acids and l-alkenyl iodides. Tetrahedron Lett. 24:2513-2516.
Cuvigny, T., Herve Du Penhoat, C., and Julia, M. 1987. Syntheses with sulfones. XLVII. Stereoselective access to 1,3-and 1,4-dienes through hydrogenolysis of benzenesulfonyldienes. Application to pheromone synthesis. Tetrahedron. 43:859-872.
Descoins, C., Samain, D., LaLanne-Cassou, B., and Gallois, M. 1977. Syntheses stereoselectives des acetoxy-1 dodecadienes 7E, 9E, et 7E, 9Z, attractifs sexuels pour le male de l`eudemis de la vigne: Lobesia (Polychrosis) botrana Den. et Schiff. Bull. Soc. Chim. Fr. 941-946.
Dressaire, G., and Langlois, Y. 1980. Pyridines as precursors of conjugated diene pheromones. II. Stereoselective synthesis of (7E, 9Z)-dodecadien-1-yl acetate, sex pheromone of Lobesia botrana. Tetrahedron Lett. 21:67-70.
Henrick, C.A. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889.
Ideses, R., Klug, J.T., Shani, A., Gothilf, S., and Gurevitz, E. 1982. Sex pheromone of the European grapevine moth, Lobesia botrana Schiff. (Lepidoptera: Tortricidae): synthesis and effect of isomeric purity on biological activity. J. Chem. Ecol. 8:195-200.
Kovalev, B.G., Ishchenko, R.I., Roska, G., Nedopekina, S.F., and Platon, Y.Y. 1978. Synthesis of trans-8, trans-10-dodecadienol and the acetate of trans-7, cis-9-dodecadienol. Khemoretsept. Nasek. 33.
Kukovinets, O.S., Kasradze, V.G., Chernukha, E.V., Odinokov, V.N., Galin, B.Z., Abdullin, M.I., Fedorov, P.I., and Tolstikov, G.A. 2000. Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXII. New synthetic route to 7E,9Z-dodecadien-1-yl acetate, pheromone of the leaf roller moth (Lobesia botrana). Russ. J. Org. Chem. 36:211-213.
Kulkarni, S.M., Mamdapur, V.R., and Chadha, M.S. 1984. Synthesis of dienic pheromones of codling moth & grape vine moth. Ind. J. Chem. 23B:1208.
Kuroda, S., Katsuki, T., and Yamaguchi, M. 1987. Stereoselective synthesis of (2E,4Z)-dien-1-ols; key intermediates for synthesis of sex pheromones of silk worm and of grape vine moth. Tetrahedron Lett. 28:803-804.
Labovitz, J.N., Henrick, C.A., and Corbin, V.L. 1975. Synthesis of (7E,9Z)-7,9-dodecadien-1-yl acetate, a sex pheromone of Lobesia botrana. Tetrahedron Lett. 16:4209-4212.
Negishi, E.-I., and Abramovitch, A. 1977. A highly efficient chemo-, regio-, and stereoselective synthesis of (7E,9Z)-dodecadien-1-yl acetate, a sex pheromone of Lobesia botrana, via a functionalized organoborate. Tetrahedron Lett. 18:411-414.
Odinokov, V.N., Ishmuratov, G.Y., Sokol' skaya, O.V., Ladenkova, I.M., Gubaidullin, L.Y., Muslukhov, R.R., and Tolstikov, G.A. 1993. Insect pheromones and their analogues. XLV. Synthesis of mono- and dienic components of insect pheromones from isopropyl nona-3E,8-dienoate. Chem. Nat. Comp. 29:123-127.
Ratovelomanana, V., and Linstrumelle, G. 1981. A convenient preparation of trans (or cis)-1-chloroalkenes from trans (or cis)-1,2-dichloroethylene: a new synthesis of the sex pheromone of Lobesia botrana. Tetrahedron Lett. 22:315-318.
Roelofs, W.L., Kochansky, J., Carde, R., Arn, H., and Rauscher, S. 1973. Sex attractant of the grape vine moth, Lobesia botrana. Mitt. Schweiz. Entomol. Ges. 46:71-73.
Roshka, C.K., and Olot, I.N. 1980. The synthesis and biological activity of trans-7, cis-9-dodecadienyl acetate. Khemorersept Nasek. 69.
Rossi, R., Carpita, A., and Quirici, M.G. 1981. Dienic sex pheromones. Stereoselective syntheses of (7E,9Z)-7,9-dodecadien-1-yl acetate. (E)-9,11-dodecadien-1-yl acetate, and of (9Z,11E)-9,11-tetradecadien-1-yl acetate by palladium catalyzed reactions. Tetrahedron. 37:2617-2623.
Tsuboi, S., Masuda, T., and Takeda, A. 1982. Highly stereocontrolled synthesis of (2E,4Z)-dienoic esters with alumina catalyst. lts application to total syntheses of flavor components and insect pheromones. J. Org. Chem. 47:4478-4482.
Ujvary, I., Kis-Tamas, A., and Novak, L. 1985. Simple and economic syntheses of some (Z)-7-and (Z)-9-alkenyl acetates and of (E,Z)-7,9-dodecadien-1-yl acetate, the sex pheromone of the European grapevine moth, using aleuritic acid as a common starting material. J. Chem. Ecol. 11:113-124.
Woerlee, E.F.G., Bosma, R.H.A., Van Eijl, J.M.M., and Mol, J.C. 1984. Metathesis of conjugated dienes: a possible way to synthesize insect pheromones and other specialty chemicals Appl. Catalysis. 10:219.
Yasuda, A., Tanaka, S., Yamamoto, H., and Nozaki, H. 1979. A highly stereospecific procedure for the transformation of allylic alcohols into 1,3-dienes. Bull. Chem. Soc. Jpn. 52:1752-1756.

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