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Compound - Z6-21-11Kt


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Formula: C21H40O 
CAS#: 54844-65-4 
MW: 308.55 

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

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Reference(s) for synthesis of (Z)-6-Heneicosen-11-one

Akermark, B., and Ljungqvist, A. 1978. Eutectic potassium-sodium-aluminum chloride as a mild catalyst for ene reactions: simple synthesis of the sex pheromone from Douglas fir tussock moth. J. Org. Chem. 43:4387-4388.
Bestmann, H.J., and Schmidt, M. 1985. Pheromone 51. Synthese von ungesaettigten pheromonketonen aus Orgyia pseudotsugata (Douglas fir tussock moth) und Carposina niponensis (peach fruit moth). Tetrahedron Lett. 26:6171-6174.
Cahiez, G., Alexakis, A., and Normant, J.F. 1980. Simple stereospecific synthesis of the insect sex pheromones of Cossus cossus, Eupoecilia ambiguella, and Orgyia pseudotsugata. Tetrahedron Lett. 21:1433-1436.
Fernandez, S., Quintanilla, R., and Hernandez, J.E. 1983. Reductive cleavage of 2-acyl tetrahydrofuranes. Synthesis of (Z)-6-heneicosen-11-one, pheromone of the Douglas fir tussock moth. Synth. Comm. 13:621.
Fetizon, M., and Lazare, C. 1978. A rapid and convenient synthesis of tbe sex pheromone of the Douglas fir, Lepidoptera Orgyia pseudotsugata. J. Chem. Soc. Perkin Trans. 1:842-844.
Henrick, C.A. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889.
Hernandez, J.E., Cisneros, A., and Fernandez, S. 1983. Short syntheses of unsaturated aliphatic ketone pheromones. Synth. Comm. 13:191.
Kocienski, P.J., and Cernigliaro, G.J. 1976. A synthesis of (Z)-6-heneicosen-11-one. The sex pheromone of the Douglas fir tussock moth. J. Org. Chem. 41:2927-2928.
Kondo, K., and Muraitashi, S.-I. 1979. Selective transformation of organoboranes to Grignard reagents by using pentane-1,5-di(Magnesium bromide). Syntheses of the pheromones of Southern armyworm moth and Douglas fir tussock moth. Tetrahedron Lett. 20:1237-1240.
Larson, G.L., Hernandez, D., de Lopez-Cepero, I.M., and Torres, L.E. 1985. Reaction of alpha-silyl esters with Grignard reagents: a synthesis of ß-keto silanes and ketones. Preparation of the Douglas fir tussock moth pheromone. J. Org. Chem. 50:5260-5267.
Mori, K., Uchida, M., and Matsui, M. 1977. Synthesis of aliphatic insect pheromones from alicyclic starting materials. (Z)-6-heneicosen-11-one and (Z)-8-dodecenyl acetate. Tetrahedron. 33:385-387.
Mundy, B.P., and Bjorklund, M. 1985. Novel synthesis of the sex pheromone of the Douglas-fir tussock moth (Orgyia pseudotsugata) and solenopsin A, a constituent of fire ant venom. Tetrahedron Lett. 26:3899-3902.
Murata, Y, Inomata, K., Kinoshita, H., and Kotake, H. 1983. A convenient method for the synthesis of acyclic ketones. Synthesis of sex pheromone of Douglas fir tussock moth. Bull. Chem. Soc. Jpn. 56:2539.
Muto, S.-E., and Mori, K. 2003. Synthesis of the four components of the female sex pheromone painted apple moth, Teia anartoides. Biosci. Biotechn. Biochem. 67:1559-1567.
Naoshima, Y., Ike, H., Ogawa, T., Nakayama, T., and Kondo, H. 1984. An easy synthesis of (E)-9-oxo-2-decenoic acid, the queen substance of the honey bee, and (Z)-6-heneicosen-11-one, the sex pheromone of the Douglas fir tussock moth. Agric. Biol. Chem. 48:2151.
Nishiyama, H., Sakuta, K., and Itoh, K. 1984. New stereocontrolled approach to some insect pheromones via silicon-directed Beckmann fragmentations. Tetrahedron Lett. 25:223-226.
Ousset, J.B., Mioskowski, C., Yang, Y.-L., and Falck, J.R. 1984. Enol ethers: preparation and synthetic applications. Tetrahedron Lett. 25:5903-5906.
Pramod, K., Ramanathan, H., and Subba Rao, G.S.R. 1983. Strategic synthesis based on cyclohexadienes: preparation of 2-, 2,3- and 2,4-substituted cyclohexenones: synthesis of (Z)-heneicosa-6-en-11-one. J. Chem. Soc. Perkin Trans. 1:7-10.
Reddy, G.B., and Mitra, R.B. 1986. Acetone dimethyl hydrazone: useful synthon for the synthesis of pheromones with keto and spiro ketal functions. Synth. Comm. 16:1723.
Reddy, G.B., and Mitra, R.B. 1987. A simple and short synthesis of Z-6-heneicosen-11-one and Z-1,6-heneicosen-11-one, the sex pheromones of Douglas-fir tussock moth. Synth. Comm. 17:893.
Reddy, P.S., Sahasrabudhe, A.B., and Yadav, J.S. 1983. A convenient synthesis of (Z)-6-heneicosen-11-one - a sex pheromone of the Douglas-fir tussock moth. Synth. Comm. 13:379.
Schäfer, H.J. 1979. Recent synthetic applications of kolbe electrolysis. Chem. Phys. Lipids. 24:321-333.
Scholz, D. 1984. Ketosulfone als ethylencarbanionenaequivalente: die synthese von 6-nonen-1-ol, 7-dodecen-1-ol-acetat und 6-heneicosen-11-on, drei Insektenpheromonen. Sci. Pharm. 52:151.
Smith, L.M., Smith, R.G., Loehr, T.M., Daves, G.D., Jr., Daterman, G,E., and Wohler, R.H. 1978. Douglas fir tussock moth pheromone: identification of a diene analogue of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6-, and 3,6-heneicosadien-11-ones. J. Org. Chem. 43:2361-2366.
Smith, R.G., Daterman, G.E., and Daves, G.D., Jr. 1975. Douglas fir tussock moth: sex pheromone identification and synthesis. Science. 188:63-64.
Smith, R.G., Daves, G.D., Jr., and Daterman, G.E. 1975. Synthesis of (Z)-6-heneicosen-11-one. Douglas fir tussock moth sex attractant. J. Org. Chem. 40:1593-1595.
Sokolovskaya, S.V. 1980. Simple synthesis of (Z)-6-heneicosen-11-one - sex pheromone of Orgyia pseudotsugata. Khim. Prir. Soedin. 102.
Sonnet, P.E. 1983. Improved preparations of alkyne nitriles, acetates, and alcohols. Application to the synthesis of the sex pheromone components of the Douglas fir tussock moth and peach fruit moth. J. Chem. Ecol. 9:551-560.
Trost, B.M., and Ornstein, P.L. 1981. A chemoselective desulfurization method via homogeneous Nickel catalysis. Tetrahedron Lett. 22:3463-3466.
Vig, O.P., Sharma, M.L., Verma, N.K., and Malik, N. 1980. A new synthesis of (Z)-heneicos-6-en-11-one, sex pheromone of Douglas fir, Lepidoptera Orgyia pseudotsugata. Ind. J. Chem. B. 19:950.
Wang, K.K., and Chu, K.-H. 1984. Preparation of (Z)-alkenes, ketones, and alkynes via trialkyltin chloride induced intramolecular transfer reaction of Lithium 1-alkynyltrialkylborates. Stereoselective synthesis of the sex pheromones of the Douglas fir tussock moth, the gypsy moth, and the wild silkmoth Antheraea polyphemus. J. Org. Chem. 49:5175-5178.
Wenkert, E., Ferreira, V.F., Michelotti, E.L., and Tingoli, M. 1985. Synthesis of acyclic, cis olefinic pheromones by way of Nickel-catalyzed Grignard reactions. J. Org. Chem. 50:719-721.
Williams, H.J., Jr. 1977. I. Preparation of pheromones through cleavage reactions of ß-halo-alpha,ß-unsaturated ketones. II. Preparation of pheromones and pheromone analogues using other methods. III. Preparation of optically active alpha-methylene-gamma-lactones, Ph. D. thesis, University of North Carolina, Raleigh, NC.

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