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Compound - E9,11-12Ac


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(E)-9,11-Dodecadienyl acetate
(E)-9,11-Dodecadienyl acetate

Formula: C14H24O2 
CAS#: 50767-78-7 
MW: 224.34 

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

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Reference(s) for synthesis of (E)-9,11-Dodecadienyl acetate

Babler, J.H. and Martin, M.J. 1977. A facile synthesis of the sex pheromone of the red bollworm moth from 10-undecen-1-ol. J. Org. Chem. 42:1799-1800.
Babler, J.H., and Invergo, B.J. 1979. A convenient stereoselective route to the sex pheromone of the red bollworm moth via an allylic sulfenate to sulfoxide rearrangement. J. Org. Chem. 44:3723-3724.
Balezina, G.G., Ishmuratov, G.Yu., Odinokov, V.N., Selimov, F.A., Dzhemilev, U.M., and Tolstikov, G.A. 1984. Insect pheromones and their analogues. lX. Stereospecific synthesis of (Z)-dodeca-9,11-dienyl acetate, a component of the sex pheromone of the cotton bollworm moth Diparopsis castanea. Chem. Nat. Prod. 354.
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.
Bloch, R., Abecassis, J., and Hassan, D. 1984. Une synthese hautement stereoselective de dienes conjugues (E). Can. J. Chem. 62:2019.
Bloch, R., and Abecassis, J. 1982. A highly stereoselective synthesis of (E)-1-substituted- 1,3-dienes. Tetrahedron Lett. 23:3277-3280.
Cardillo, G., Orena, M., Porzi, G., and Sandri, S. 1980. A stereospecific synthesis of 12-acetoxy-1,3-dodecadiene, the sex pheromone of Diparopsis castanea (Hampson). Gaz. Chim. Ital. 110:523.
Herve du Penhoat, C., and Julia, M. 1986. Synthesis with sulfones. XLIV. Stereoselective preparation of E,E-1,3-dienes by elimination of benzenesulfinic acid from E homoallylic sulfones. Tetrahedron. 42:4807-4816.
Ishibashi, H., Komatsu, H., Maruyama, K., and Ikeda, M. 1985. Novel synthesis of 1,3-dienes from 1-alkenes via "ene" reaction with Pummerer rearrangement product a short synthesis of the sex pheromone of the red bollworm moth. Tetrahedron Lett. 26:5791-5794.
Knox, G.R., and Thom, I.G. 1981. Simple, stereospecific syntheses of some insect pheromones using the -Fe(CO)3, protecting group. J. Chem. Soc. Chem. Comm. 8:373-374.
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.
Mandai, T., Yasuda, H., Kaito, M., Tsuji, J., Yamaoka, R., and Fukami, H. 1979. Synthesis of 12-acetoxy-1,3-dodecadiene an insect sex pheromone of the red bollworm moth, from a butadiene telomer. Tetrahedron. 35:309-311.
Michelot, D. 1983. Highly stereoselective synthesis of acetates of mono- and diunsaturated alcohols and analogous aldehydes, components of Lepidopteran sex pheromones, using tetrakis[triphenylphosphine]-palladium. Synthesis. 2:130-134.
Mori, K. 1974. Simple synthesis of sex pheromones of codling moth and red bollworm moth by the coupling of Grignard reagents with allylic halides. Tetrahedron. 30:3807-3810.
Nesbitt, B.F., Beevor, P.S., Cole, R.A., Lester, R., and Poppi, R.G. 1973. Synthesis of both geometric isomers of the major sex pheromone of the red bollworm moth. Tetrahedron Lett. 14:4669-4670.
Ochiai, M., Ukita, T., and Fujita, E. 1983. Stereoselective syntheses of E- and Z-9,11-dodecadien-1-yl acetates: the major sex pheromones of the red bollworm moth. Chem. Pharm. Bull. 31:1641.
Ranganathan, S., Kumar, R., and Maniktala, V. 1982. A practical, convenient, and highly stereospecific synthesis of 1-acetoxy (E) 9,11-dodecadiene. The insect sex pheromone of bollworm moth. Synth. Comm. 12:921.
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.
Rossi, R., Carpita, A., and Gaudenzi, M.L. 1981. Highly stereoselective synthesis of (Z)-9,11-dodecadien-1-yl acetate: a sex pheromone component of Diparopsis castanea Hmps. Synthesis. 5:359360.
Tanaka, S., Yasuda, A., Yamamoto H., and Nozaki, H. 1975. A general method for the synthesis of 1,3-dienes. Simple syntheses of beta- and trans-alpha-farnesene from farnesol. J. Am. Chem. Soc. 97:3252-3254.
Tsai, D.J.S., and Matteson, D.S. 1981. A stereocontrolled synthesis of Z and E terminal dienes from pinacol E-1-trimethylsilyl-1-propene-3-boronate. Tetrahedron Lett. 22:2751-2752.
Vig, O.P., Sharma, M.L., Verma, N.K., and Malik, N. 1980. Synthesis of 9-(E)-dodecenyl acetate & 9-(E),11-dodecadienyl acetate, female sex pheromones of red bollworm moth, Diparopsis castanea Hmps. Ind. J. Chem. B. 19:692-694.
Wollenberg, R.H., and Peries, R. 1979. Efficient syntheses of insect sex pheromones emitted by the boll weevil and the red bollworm moth. Tetrahedron Lett. 20:297-300.
Yamada, S., Ohsawa, H., Suzuki, T., and Takayama, H. 1986. Stereoselective synthesis of (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step. J. Org. Chem. 51:4934-4940.
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 2018. The Pherobase: Database of Pheromones and Semiochemicals. <>.
2003-2018 The Pherobase - Extensive Database of Pheromones and Semiochemicals. Ashraf M. El-Sayed.
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