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Compound - trans-verbenol [trans-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol]

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trans-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol Formula:  C10H16O  CAS#:  1820-09-3  MW:  152.23  [MS]  [ NMR ]  [ Kovats ]  [Behavioural function]  [Occurrence in flower]

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Reference(s) for synthesis of trans-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol [trans-verbenol] Bakke, A., Froyen, P., and Skattebol, L. 1977. Field response to a new pheromonal compound isolated from Ips typographus. Naturwissenschaften. 64:98.   Cooper, M.A., Salmon, J.R., Whittaker, D., and Scheidegger, U. 1967. Stereochemistry of the verbenols. J. Chem. Soc. B: Phys. Org. 1259-1261.   Mori, K. 1976. Synthesis of optically pure (+)-trans-verbenol and its antipode, the pheromone of Dendroctonus bark beetles. Agric. Biol. Chem. 40:415.   Mori, K., Mizumachi, N., and Matsui, M. 1976. Synthesis of optically pure (1S,4S,5S)-2-pinen-4-ol (cis-verbenol) and its antipode, the pheromone of Ips bark beetles. Agric. Biol. Chem. 40:1611.   Nishino, C., and Takayanagi, H. 1979. Conformation of pinan-3-ol derivatives. Agric. Biol. Chem. 431:2399.   Nishino, C., and Takayanagi, H. 1979. Conformational analysis of verbenols and related alcohols by PMR spectra with a chemical shift reagent. Agric. Biol. Chem. 43:2323.   Nishino, C., and Takayanagi, H. 1979. Synthesis of verbenols and related alcohols and their PMR spectra with shift reagent. Agric. Biol. Chem. 43:1967.   Pitman, G.B., Vite, J.P., Kinzer, G.W., and Fentiman, A.F., Jr. 1968. Bark beetle attractants trans-verbenol isolated from Dendroctonus. Nature. 218:168.   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.   Renwick, J.A.A. 1967. Identification of two oxygenated terpenes from the bark beetles Dendroctonus frontalis and Dendroctonus brevicomis. Contrib. Boyce Thompson Inst. 23:355.   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.   Silverstein, R.M., Rodin, J.O., Wood, DL., and Browne, L.E. 1966. Identification of two new terpene alcohols from frass produced by Ips confusus in ponderosa pine. Tetrahedron. 22:1929-1936.   Takayanagi, H., and Nishino, C. 1980. Synthesis of configurational isomers of verbenyl carboxylic acid and related compounds. Agric. Biol. Chem. 44:2877.   Whitham, G.H. 1961. The reaction of alpha-pinene with lead tetra-acetate. J. Chem. Soc. 2232-2236.