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Compound - ipsdienol


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Formula: C10H16O 
CAS#: 35628-00-3 
MW: 152.23 

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

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Reference(s) for synthesis of 2-Methyl-6-methylene-2,7-octadien-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.
Bertrand, M., and Viala, J. 1978. Nouvelle approche des derives du myrcene par transposition thermique des orthoesters alleniques mixtes. Tetrahedron Lett. 19:2575-2578.
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.
Francke, W., Sauerwein, P., Vite, J.P., and Klimetzek, D. 1980. The pheromone bouquet of Ips amitinus. Naturwissenschaften. 67:147.
Garbers, C.F., and Scott, F. 1976. Terpenoid synthesis. V. Electrophilic addition reaction in the synthesis of the ocimenones, the rose oxides, and a pheromone of Ips paraconfusus. Tetrahedron Lett. 17:1625-1628.
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.
Hosomi, A., Saito, M., and Sakurai, H. 1979. 2-trimethylsilylmethyl-1,3-butadiene as a novel reagent for isoprenylation. New access to ipsenol and ipsdienol, pheromones of Ips paraconfusus. Tetrahedron Lett. 20:429-432.
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.
Kozhich, O.A., Pyzhyanova, N.E., Segal, G.M., and Torgov, I.V. 1983. Synthesis of ipsdienol, a component of aggregation pheromone of bark beetles of the IPS genus. Bioorg. Khim. 9:1658.
Liu, M., and Silverstein, K.M. 1985. Synthesis of (+)-ipsdienol from glutamic acid, (CHIN). Huaxue Xuebao. 43:467.
Mori, K. 1974. A new synthesis of 2-methyl-6-methylene octa-2,7-dien-4-ol, a component of the pheromone of California five-spined Ips. Agric. Biol. Chem. 38:2045.
Mori, K. 1976. Absolute configuration of (+)-ipsdienol, the pheromone of Ips paraconfusus Lanier, as determined by the synthesis of its (R) (-) isomer. Tetrahedron Lett. 17:1609-1612.
Mori, K., Takigawa, T., and Matui, T. 1979. Synthesis of optically active forms of ipsdienol and ipsenol. The pheromone components of Ips bark beetles. Tetrahedron. 35:933-940.
Ohloff, G., and Giersch, W. 1977. Access to optically active Ipsdienol from verbenone. Helv. Chim. Acta. 60:1496-1500.
Reece, C.A., Rodin, J.O., Brownlee, R.G., Duncan, W.G., and Silverstein, R.M. 1968. Synthesis of the principal components of the sex attractant from male Ips confusus frass: 2-methyl-6-methylene-7-octen-4-ol, 2-methyl-6methylene-2,7-octadien-4-ol, and (+)-cis-verbenol. Tetrahedron. 24:4249-4256.
Riley, R.G., Silverstein, R.M., Katzenellenbogen, J.A., and Lenox, R.S. 1974. Improved synthesis of 2-methyl-6methylene-2,7-octadien-4-ol, a pheromone of Ips paraconfusus, and an alternate synthesis of the intermediate, 2-bromomethyl-1,3-butadiene. J. Org. Chem. 39:1957-1958.
Sharpless, K.B., and Laver, R.F. 1973. A mild procedure for the conversion of expoxides to allylic alcohols. The first organoselenium reagent. J. Am. Chem. Soc. 95:2697-2699.
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.

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