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Compound - Z9-23Hy
 


Bedoukain

 
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(Z)-9-Tricosene
(Z)-9-Tricosene

Formula: C23H46 
CAS#: 27519-02-4 
MW: 322.61 

[MS]  [ NMR ]  [ Kovats ]  [Behavioural function]  [Occurrence in plant]  [Chemdraw





Dots surface:


Reference(s) for synthesis of (Z)-9-Tricosene



Abe, K., Yamasaki, T., Nakamura, N., and Sakan, T. 1977. The studies of the activated compound. III. A synthesis of muscalure: (Z)-9-tricosene. Bull. Chem. Soc. Jpn. 50:2792.
 
Bestmann, H.J., Vostrowsky, O., and Platz, H. 1974. Pheromone. V. Eine stereoselektive synthese des sexuallockstoffes der stubenfliege (Musca domestica). Chem. Zeit. 98:161.
 
Brovko, V.V., Mazur, V.G., Vlasov, A.A., Shishmaki, T.G., Strepkova, L.S., and Evstifeev, A.V. 1980. Synthesis of sex pheromones of codling and plum fruit moths and the housefly. Khim. Sel' sk. Khoz. 18:30.
 
Brown, H.C., and Wang, K.K. 1986. Vinylic organoboranes. III. Pheromones via organoboranes, l. Stereospecific synthesis of straight-chain Z-monoolefinic insect pheromones via lithium(1-alkynyl)-trialkylborates. J. Org Chem. 51:4514-4517.
 
Cargill, R.L., and Rosenblum, M.G. 1972. Synthesis of the housefly sex attractant. J. Org. Chem. 37:3971-3971.
 
Carlson, D.A., Doolittle, R.E., Beroza, M., Rogoff, W.M., and Gretz, G.H. 1974. Muscalure and related compounds. I. Response of houseflies in olfactometer and pseudofly tests. Agric. Food Chem. 22:194.
 
Carlson, D.A., Mayer, M.S., Silhacek, D.L., James, J.D., Beroza, M., and Bierl, B.A. 1974. Sex attractant pheromone of the house fly: isolation, identificaion and synthesis. Science. 174:76.
 
Carroll, F.A., Boldridge, D.W., Lee, J.T., Martin, R.R., Turner, M.J., and Venable, T.L. 1980. Synthesis and field tests of analogues of the housefly pheromone (Z)-9 tricosene. J. Agric. Food Chem. 28:343-346.
 
Chan, T.H., and Koumaglo, K. 1985. Silicon in organic synthesis. Stereoselective synthesis of some insect sex pheromones. J. Organomet. Chem. 285:109-120.
 
Cormier, R.A., Phan, M.D., Graddis, T., and Singer, R. 1979. A student synthesis of the housefly sex attractant. J. Chem. Ed. 56:345.
 
Dinunno, L., and Flario, S. 1975. Simple synthesis of sex pheromones of the housefly and tiger moths by transition metalcatalyzed olefin cross metathesis reactions. Chim. Ind. (Milano). 57:242.
 
Eiter, K. 1972. Neue synthese des tricosen-(9-cis) ("muscalure"), eines attraktivstoffes der hausfliege. Naturwissenschaften. 59:468.
 
Gribble, G.W., Sanstead, J.K., and Sullivan, J.W. 1973. One-step synthesis of the housefly sex attractant (Z)-tricos-9ene (muscalure). J. Chem. Soc. Chem. Comm. 19:735-736.
 
Henrick, C.A. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889.
 
Ho, T.-L., and Wong, C.M. 1974. A synthesis of muscalure, the housefly sex attractant. Can. J. Chem. 52:1923-1924.
 
Ito, S., Saito, N., Hatakeda, K., Ikushima, Y., Gogo, T., and Asano, T. 1984. Synthesis of muscalure. Yukagaku. 33:454.
 
Kovalev, B.G., Stan, V.V., Antoch, T.K., Konyukhov, V.P., and Nedopekina, S.F. 1977. Synthetic studies of attracting substances (sexual attractants) of insects. III. Convenient method of preparing higher dialkylacetylenes. Synthesis of muscalure, the attractant of the housefly Musca domestica L. Zh. Org. Khim. 13:2049-2052.
 
Krasavtsev, I.I. 1979. Synthesis of Arctiidae and Musca domestica sex pheromones. Ukrainsky Khim. Zh. 45:74.
 
Kuepper, F.W., and Streck, R. 1975. Synthese von insektenpheromonen an metathesekatalysatoren. Chem. Zeit. 99:464.
 
Kuepper, F.W., and Streck, R. 1976. Synthese von insektenlockstoffen an metathesekatalysatoren. Z. Naturforsch. B. 31:1256.
 
LeBigot, Y., Delmas, M., and Gaset, A. 1983. Direct synthesis of Dipteran sex pheromones by the Wittig reaction in a heterogeneous medium. J. Agric. Food Chem. 31:1096-1098.
 
Moiseenkov, A., Schaub, B., Margot, C., and Schlosser, M. 1985. A new stereoselective synthesis of (Z)-9-tricosene, the sex attractant of the common housefly. Tetrahedron Lett. 26:305-306.
 
Nakamura, R., and Echigoya, E. 1977. Metathesis of oleyl chloride. Chem. Lett. 1227.
 
Naoshima, Y., Ozawa, H., Takenami, Y., Wakabayashi, S., and Hayashi, S. 1981. Convenient synthesis of muscalure, the housefly sex pheromone. Agric. Biol. Chem. 45:1723.
 
Nomura, M. and Fujihara, Y. 1985. Synthesis of acyclic monoene hydrocarbons as a sex pheromone of Musca domestica. Yukagaku. 34:62.
 
Odinokov, V.N., Galeeva, R.I., Kargapol'tseva, T.A., and Tolstikov, G.A. 1985. Ozonolysis of alkenes and reactions of polyfunctional compounds. XXVI. Synthesis of muscalure - the sex pheromone of the house fly Musca domestica. Zhur. Org. Khim. 21:735.
 
Odinokov, V.N., Ishmuratov, G.Y., Balezina, G.G., Vakhitov, R.S., and Tolstikov, G.A. 1985. Insect pheromones and their analogues. XIV. The synthesis of muscalure as a sex pheromone of Musca domestica. Khim. Prir. Soed. 401.
 
Odinokov, V.N., Tolstikov, G.A., Galeyeva, R.I., and Kargapol'tseva, T.A. 1982. A novel stereospecific synthesis of muscalure, the sex pheromone of house fly (Musca domestica). Tetrahedron Lett. 23:1371-1372.
 
Pop, L., and Hodosan, F. 1982. Synthesis of (Z)-9-tricosene (muscalure). Rev. Roum. Chim. 27:545.
 
Richter, I., and Mangold, H.K. 1973. Synthesis of muscalure and homologous hydrocarbons. Chem. Phys. Lipids. 11:210-214. .
 
Rossi, R. 1975. Simple synthesis of sex pheromones of the housefly and tiger moths by transition metal-catalyzed olefin cross-metathesis reactions. Chim. Ind. (Milano). 57:242.
 
Schäfer, H.J. 1979. Recent synthetic applications of kolbe electrolysis. Chem. Phys. Lipids. 24:321-333. .
 
Shani, A. 1979. An efficient synthesis of muscalure from Jojoba oil or oleyl alcohol. J. Chem. Ecol. 5:557-564.
 
Subramanian, G.B.V., and Michael, G. 1986. Synthesis from aleuritic acid of (Z)-9-tricosene (muscalure): the sex attractant of housefly. Chem. Ind. 749.
 
Subramanian, G.B.V., Mehrotra, A., and Mehrotra, K. 1986. Enamine condensation on derivatives of aleutitic acid and synthesis of (Z)-9-tricosene, (muscalure), its (E)-isomer, and (E)-13-heptacosene. Tetrahedron. 42:3967-3972.
 
Uebel, E.C., Schwarz, M., Lusby, W.R., Miller, R.W., and Sonnet, P.E. 1978. Cuticular non-hydrocarbons of the female house fly and their evaluation as mating stimulants. Lloydia. 41:63.
 
Verba, G.G., Abdukakharov, V.S., and Abduvakhabov, A.A. 1985. Synthesis of muscalure - the pheromone of Musca domestica. Khim. Prir. Soedin. 698.
 
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.
 
Yadav, A.K., and Tissot, P. 1984. Electrochemical synthesis of the sex attractant pheromone of the housefly: (Z)-9-tricosene. Helv. Chim. Acta. 67:1698-1701.
 
Yadav, J.S., and Reddy, P.S. 1984. A convenient reduction of dialkylated tosylmethyl isocyanide. Tetrahedron Lett. 25:4025-4028.
 

 
Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <http://www.pherobase.com>.
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