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Compound - E10Z12-16OH
 


Bedoukain

 
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(E,Z)-10,12-Hexadecadien-1-ol
(E,Z)-10,12-Hexadecadien-1-ol

Formula: C16H30O 
CAS#: 1002-94-4 
MW: 238.41 

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





Dots surface:


Reference(s) for synthesis of (E,Z)-10,12-Hexadecadien-1-ol



Bestmann, H.J., Vostrowsky, O., Paulus, H., Billmann, W., and Stransky, W. 1977. Pheromone XI. Eine aufbaumethode fuer konjugierte (E),(Z)-diene. Synthese des bombykols, seiner derivate und homologen. Tetrahedron Lett. 18:121-124.
 
Brown, H.C., and Somayaji, V. 1984. Convenient procedure for the synthesis of (E)-1-bromo-1-alkenes and (Z)-1-iodo-1-alkenes Synthesis. 11:919-920.
 
Butenandt, A., and Hecker, E. 1961. Synthese des bombykols, des sexuallockstoffes des seidenspinners, und seiner geometrischen isomeren. Angew. Chem. 73:349.
 
Butenandt, A., Hecker, E., Hopp, M., and Koch, W. 1962. Über den sexuallockstoff des seidenspinners. IV. Die synthese des bombykols und der cis-trans-isomeren hexadecadien-(10,12)-ole-(1). Liebigs Ann. Chem. 658:39-64.
 
Descoins, C., and Samain, D. 1976. Ouverture acide d'alcools cyclopropaniques acetyleniques complexes par le dicovalt octacarbonyle. Obtention stereoselective d'enynes conjugues E, precurseurs de dienes conjugues E,Z. Tetrahedron Lett. 17:745-748.
 
Eiter, K. 1970. Insektensexuallockstoffe. Fortschr. Chem. Org. Naturstoffe. 28:204.
 
Khrimian, A., Klun, J.A., Hijji, Y., Baranchikov, Y.N., Pet'ko, V.M., Mastro, V.C., and Kramer, M.H. 2002. Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, Lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth. J. Agric. Food Chem. 50:6366-6370.
 
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.
 
Kuwahara, Y., and Yen, L.T.M. 1979. Identification of bombykol in Bombyx mandarina females. Appl. Entomol. Zool. 14:114.
 
Kuwahara, Y., Mori, N., Yamada, S., and Nemoto, T. 1984. Evaluation of bombykol as the sex pheromone of Bombyx mandarina. Appl. Entomol. Zool. 19:265.
 
Miyaura, N., Suginome, H., and Suzuki, A. 1983. New stereospecific syntheses of pheromone bombykol and its three geometrical isomers. Tetrahedron Lett. 24:1527-1530.
 
Negishi, E., Lew, G., and Yoshida, T. 1973. Stereoselective synthesis of conjugated trans-enynes readily convertible into conjugated cis, trans-dienes and its application to the synthesis of the pheromone bombykol. J. Chem. Soc. Chem. Comm. 22:874-875.
 
Normant, J.F., Commercon, A., and Villieras, J. 1975. Synthese d'enynes et de dienes conjugues a l'aide d'organocuivreux vinyliques. Application a la synthese du bombykol. Tetrahedron Lett. 16:1465-1468.
 
Odinokov, V.N., Ishmuratov, G.Y., Ladenkova, I.M., Sokol' skaya, O.V., Muslukhov, R.R., Akhmetova, V.R., Gorobets, E.V., Kuchin, A.V., and Tolstikov, G.A. 1993. Insect pheromones and their analogues: XLVIII. A convenient synthesis of the 10E,12Z- and 10E,12E- isomers of hexadecadien-1-ol and of hexadeca-10E,12Z-dienal - components of the sex pheromone of the silkworm moth. Chem. Nat. Comp. 29:668-673.
 
Samain, D., and Descoins, C. 1979. Etude de la stereoselectivite de la transposition de Claisen applique aux enynols secondaires. Synthese stereo selective du bombykol: hexadecadiene-10E,12Z ol-1 et de ses derives; bombykal et acetate de bombykol. Bull. Soc. Chim. Fr. 71-76.
 
Truscheit, E., and Eiter, K. 1962. Synthese der vier isomeren hexadecadien-(10,12)-ole-(1). Liebigs Ann. Chem. 658:65-90.
 
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.
 
Tsuboi, S., Masuda, T., Makino, H., and Takeda, A. 1982. Highly stereocontrolled synthesis of (2E,4Z)-dienoic esters by alumina catalyst. Tetrahedron Lett. 23:209-212.
 
Uenishi, J., Kawahama, R., Izaki, Y., and Yonemitsu, O. 2000. A facile preparation of geometrically pure alkenyl, alkynyl, and aryl conjugated Z-alkenes: stereospecific synthesis of bombykol. Tetrahedron. 56:3493-3500.
 

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