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Semiochemicals & Taxa


Invasive spp.
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« Previous Compoundipsdienone    Next Compound »ipsenone
Compound - ipsenol


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Formula: C10H18O 
CAS#: 35628-05-8 
MW: 154.25 

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

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Reference(s) for synthesis of 2-Methyl-6-methylene-7-octen-4-ol

Baibero, A., Garcia, C., and Pulido, F.J. 2001. Allylsilane-vinylcopper reagents: palladium-mediated coupling with alkenyl halides. Synthesis and Photochemical [2+2] Cyclization of (+/-)-ipsdienol. Syn. Lett. 6:824-826.
Clinet, J.C., and Linstrumelle, G. 1977. An efficient method for the preparation of conjugated allenic carbonyl compounds. The synthesis of two bark beetle pheromones. Nouv. J. Chim. 1:373.
Haslouin, J., and Rouessac, F. 1977. Coupures thermiques du type retro-diels-Alder (V), synthese du ()-ipsenol. Bull. Soc. Chim. Fr. Pt. 1:1242.
Hosomi, A., Araki, Y., and Sakurai, H. 1983. Chemistry of organosilicon compounds. 171. Isoprenylation of carbonyl compounds with 2-[(trimethylsilyl)methyl]-1,3-butadiene initiated by a catalytic amount of tetra-n-butylammonium fluoride. The most convenient route to ipsenol and ipsdienol. J. Org. Chem. 48:3122-3125.
Ikeda, N., Arai, I., and Yamamoto, H. 1986. Chiral allenylboronic esters as a practical reagent for enantioselective carbon-carbon bond formation. Facile synthesis of (-)-ipsenol. J. Am. Chem. Soc. 108:483-486.
Karlsen, J., Froyen, P., and Skattebol, L. 1976. New syntheses of the bark beetle pheromones 2-methyl-6-methylene-7-octen-4-ol (ipsenol) and 2-methyl 6-methylene-2,7-octadien-4-ol (ipsdienol). Acta Chem. Scand. B30:664-668.
Katzenellenbogen, J.A., and Lenox, R.S. 1973. The generation of allyllithium reagents by Lithium-tetrahydrofuran reduction of allylic mesitoates. A new procedure for selective allylic cross coupling and allylcarbinol synthesis. J. Org. Chem. 38:326-335.
Kondo, K., Dobashi, S., and Matsumoto, M. 1976. The reaction of 2-(1,3-butadienyl) magnesium chloride. Chem. Lett. 1077-1080.
Mori, K. 1975. Synthesis and absolute configuration of (-)-ipsenol (2-melhyl-6-methylene-7-octen-4-ol), the pheromone of Ips paraconfusus Lanier. Tetrahedron Lett. 16:2187-2190.
Mori, K. 1976. Synthesis of optically activeforms of ipsenol, the pheromone of Ips bark beetles. Tetrahedron. 32:1101-1106.
Mori, K., Takigawa, T., and Matsui, T. 1979. Synthesis of optically active forms of ipsdienol and ipsenol. The pheromone components of Ips bark beetles. Tetrahedron. 35:933-940.
Riley, R.G., Silverstein, R.M., Katzenellenbogen, J.A., and Lenox, R.S. 1974. Improved synthesis of 2-methyl-6-methylene-2,7-octadien-4-ol, a pheromone of Ips paraconfusus, and an alternate synthesis of the inter ediate, 2-bromomethyl-1,3-butadiene. J. Org. Chem. 39:1957-1958.
Silverstein, R.M., Rodin, J.O., and Wood, D.L. 1966. Sex attractants in frass produced by male Ips confusus in ponderosa pine. Science. 154:509
Vig, O.P., Anand, R.C., Kad, G.L., and Sehgal, J.M. 1970. Terpenoids. LVII. Syntheses of -farnesene and methylene isomer of tagetol. J. Ind. Chem. Soc. 47:999.
Vite, J.P., Hedden, R., and Mori, K. 1976. Ips grandicollis: field response to the optically pure pheromone. Naturwissenschaften. 63:43.
Wilson, S.R., and Phillips, L.R. 1975. Cyclobutene derivatives as isoprene equivalents in terpene synthesis: 1-cyclobutenyl methyl lithium. Tetrahedron Lett. 16:3047-3050.

Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <>.
2003-2014 The Pherobase - Extensive Database of Insect Pheromones and Semiochemicals. Ashraf M. El-Sayed.
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