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Compound - grandlure III [(Z)-(3,3-Dimethyl)-cyclohexylideneacetaldehyde]

Bedoukain RussellIPM
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Formula: C10H16O 
CAS#: 26532-24-1 
MW: 152.23 

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

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Reference(s) for synthesis of (Z)-(3,3-Dimethyl)-cyclohexylideneacetaldehyde [grandlure III]

Babler, J.H., and Coghlan, M.J. 1976. A facile method for the bishomologation of ketones to alpha,-unsaturated aldehydes: application to the synthesis of the cyclohexanoid components of the boll weevil sex attractant. Synth. Comm. 6:469.
Babler, J.H., and Mortell, T.R. 1972. A facile route to three of the four terpenoid components of the boll weevil sex attractant. Tetrahedron Lett. 13:669-672.
Bedoukian, R.H., and Wolinsky, J. 1975. A biogenetic-type synthesis of the cyclohexyl constituents of the boll weevil pheromone. J. Org. Chem. 40:2154-2156.
De Souza, J.P., and Gonsalves, A.M.R. 1978. Alternative route to three of the four terpenoid components of the boll weevil sex pheromone. J. Org. Chem. 43:2068-2069.
Ghosh, A., Banerjee, U.K., and Venkateswaran, R.V. 1986. Decarboxylation of alpha-cyanoalkylidene esters and acids. Synthesis, of cyclohexyl constituents of the pheromone of the boll weevil. J. Chem. Res. 148.
Gueldner, R.C., Tumlinson, J.H., Hardee, D.D., Thompson, A.C., Hedin, P.A., and Minyard, J.P. 1971. Identification and synthesis of the four compounds comprising the boll weevil sex attractant. J. Org. Chem. 36:2616-2621.
Harris, F.L., and Weiler, L. 1987. The stereospecific formation of an exocyclic alkene by a consecutive radical cyclizationelimination. Tetrahedron Lett. 28:2941-2944.
Mandai, T., Mizobuchi, K., Kawada, M., and Otera, J. 1984. New synthetic methods for gamma-geraniol, boll weevil pheromone, and alpha-damascone employing 2-(hydroxymethyl)-4-(phenylthio)-1-butene as a building block. J. Org. Chem. 49:3403-3406.
Pelletier, S.W., and Mody, N.V. 1976. A facile synthesis of the cyclohexyl constituents of the boll weevil sex pheromone. J. Org. Chem. 41:1069-1071.
Piva, O., and Comesse, S. 2000. Tandem Michael-Wittig-Horner reaction: one-pot synthesis of delta-substituted alpha, beta-unsaturated carboxylic acid derivatives - application to a concise synthesis of (Z)- and (E)-ochtoden-1-al. Eur. J. Org. Chem. 13:2417-2424.
Tanaka, K., Tanikaga, R., and Kaji, A. 1976. New reagents for the synthesis of alpha,-unsaturated esters: lithiated O-alkyl-S-ethoxycarbonylmethyl dithiocarbonate and thiocarbonate. Chem. Lett. 917.
Traas, P. C., Boelens, H., and Takken, H.J. 1976. Convenient synthesis of 3,3-dimelhylcyclohexylidene acetaldehyde, a sex attractant of the male boll weevil. Synth. Comm. 6:489.
Tumlinson, J.H., Hardee, D.D., Gueldner, R.C., Thompson, A.C., Hedin, P.A., and Minyard, J.P. 1969. Sex pheromones produced by male boll weevil: isolation, identification, and synthesis. Science. 166:1010.
Vig, O.P., Ram, B., and Kaur, J. 1972. Terpenoids. Part LXXV. A new synthesis of 3,3-dimethyl-delta1,-cyclohexane acetaldehyde. J. Ind.Chem.Soc. 49:1181.
Vig, O.P., Sharma, S.D., Bari, S.S., and Kumar, S.D. 1977. Terpenoids. CXXVIII. Synthesis of 7-methyl-3-methylene-6-octen-1-ol (gamma-geraniol). Ind. J. Chem. B. 15:93.
Wollenberg, R.H., and Peries, R. 1979. Efficient syntheses of insect sex pheromones emitted by the boll weevil and the red bollworm moth. Tetrahedron Lett. 20:297-300.

Citation: El-Sayed AM 2024. The Pherobase: Database of Pheromones and Semiochemicals. <>.
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