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Compound - E9-14Ac


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(E)-9-Tetradecenyl acetate
(E)-9-Tetradecenyl acetate

Formula: C16H30O2 
CAS#: 23192-82-7 
MW: 254.41 

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

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Reference(s) for synthesis of (E)-9-Tetradecenyl acetate

Bestmann, H.J., Range, P., and Kunstmann, R. 1971. Pheromone II. Synthese des essigsäure-[cis-tetradecen-(9)-yl-esters]. Chem. Ber. 104:65.
Bestmann, H.J., Stransky, W., and Vostrowsky, O. 1976. Reaktionen mit Phosphinalkylenen. XXXIII Darstellung lithiumsalz freier ylidlösungen mit Natrium-bis(trimethylsilyl)amid als Base. Chem. Ber. 109:1694.
Chattopadhyay, A., Mamdapur, V.R., and Chadha, M.S. 1983. A convenient synthesis of (E)-9-tetradecen-1-yl acetate a sex pheromone of gelechiid moth & (E)-5-decenol a sex pheromone of peach twig borer. Ind. J. Chem. 22B:1221.
Crisp, G.T., and Collis, M.P. 1988. Metathesis of functionalized alkenes. Synthesis of insect pheromones. Austr. J. Chem. 41:935-942.
Dzhumakulov, T., Yuldashev, A.M., and Abduvakhobov, A.A. 1982. Synthesis of one of the sex pheromones of Heliothis levre. Khim. Prir. Soed. 538-539.
El-Rabbat, N.A., and Mangold, H.K. 1980. A convenient method for the preparation of pheromones from inexpensive starting materials. Z. Naturforsch. C. 35:982.
Fyles, T.M., Leznoff, C.C., and Weatherston, J. 1977. The use of polymer supports in organic synthesis. XII. The total stereoselective synthesis of cis insect sex attractants on solid phases. Can. J. Chem. 55:4135.
Gardette, M., Alexis, A., and Normant, J.F. 1983. Synthesis of (Z,Z)-3,13-octadecadien-1-yl acetate. Component of the sex pheromone of Synanthedon tenuis. J. Chem. Ecol. 9:225-233.
Jacobson, M., and Harding, C. 1968. Insect sex attractants. IX. Chemical conversion of the sex attractant of the cabbage looper to the sex pheromone of the fall armyworm. J. Econ Entomol. 61:394.
Julia, M., and Stacino, J.-P. 1986. Syntheses a l'aide de sulfones. XXXVII. Synthese de trois pheromones a une double liaison Z: Z,8-DDA, Z,9-DDA; Z,9-TDA. Tetrahedron. 42:2469-2474.
Kondo, K., and Murahashi, S.-I. 1979. Selective transformation of organoboranes to Grignard reagents by using pentane1.5-di(magnesium bromide). Syntheses of the pheromones of Southern armyworm moth and Douglas fir tussock moth. Tetrahedron Lett. 20:1237-1240.
Leadbetter, G., and Plimmer, J.R. 1979. An improved preparation of some insect sex attractants: synthesis and separation of geometric isomers by formation of urea complexes. J. Chem. Ecol. 5:101-108.
Leznoff, C.C., and Fyles, T.M. 1976. Synthesis of insect sex attractants on solid phases. J. Chem. Soc. Chem. Comm. 7:251-252.
Lin, G., and Guo, G. 1980. Insect sex pheromone. Synthesis of Z-9-tetradecenyl acetate. Hua Hsueh Hsueh Pao. 30:610.
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.
Nakamura, R., Matsumoto, S., and Echigoya, E. 1976. Metathesis of alkenes having functional groups. Chem. Lett. 1019.
Nanda, B., Butalia, M.S., Patwardhan, S.A., and Gupta, A.S. 1985. Role of pheromones in integrated pest management. Behav. Physiol. Appr. Pest Manage. Pap. Natl. Semin. 73.
Rossi, R. 1977. Insect pheromones. I. Synthesis of achiral-components of insect pheromones. Synthesis. 12:817-836.
Rossi, R., Carpita, A., Gaudenzi, L., and Quirici, M.G. 1980. Insect sex pheromones. Stereoselective synthesis of several (Z)- and (E)-alken-1-ols, their acetates, and of (9Z,12E)-9,12-tetradecadien-1-yl acetate. Gaz. Chim. Ital. 110:237-246.
Sekul, A.A., and Sparks, A.N. 1967. Sex pheromone of the fall armyworm moth: isolation, identification, and synthesis. J. Econ. Entomol. 60:1270-1272.
Tamaki, Y, Noguchi, H., Yushima, T., and Hirano, C. 1971. Two sex pheromones of the smaller tea tortrix isolation, identification, and synthesis. Appl. Entomol. Zool. 6:139.
Tolstikov, G.A., Odinokov, V.N., Galeeva, R.I., Bakeeva, R.S., and Akhunova, V.R. 1979. A new stereospecific sythesis of sex pheromones of insects of the (Z)-alkenyl-1-acetate series based on selective ozonolysis of 1-methyl-1Z,5Z-cyclooctadiene. Tetrahedron Lett. 20:4851-4854.
Tolstikov, G.A., Odinokov, V.N., Galeeva, R.I., Bakeeva, R.S., and Akhunova, V.R. 1982. Pheromones of insects and their analogs. V. A new approach to the synthesis of the sex pheromones of insects of the order Lepidoptera which is based on the selective ozonolysis of 1-methylcycloocta-1Z,5Z-diene. Khim. Prir. Soed. 239.
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.
Vig, O.P., Sharma, M.L., Kumari, S., and Vohra, N. 1985. A new synthesis of (Z)-9-tetradecen-1-yl acetate. J. Chem. B. 24:962.
Voerman, S. 1979. Chemical conversion of 9-tetradecen-1-ol acetates to 3,13-octadecadien-1-ol acetates, sex attractants for male clearwing moths. J. Chem. Ecol. 5:759-766.
Vostrowsky, O., Bestmann, H.J., and Priesner, E. 1973. Struktur und aktivitaet von pheromonen. Nachr. Chem. Techn. 21:501.
Warthen, D. 1968. Synthesis of cis-9-tetradecen-1-ol acetate, the sex pheromone of the fall armyworm. J. Med. Chem. 11:371-373.

Citation: El-Sayed AM 2018. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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