Title: Grandisol
CAS Registry Number: 26532-22-9
CAS Name: (1R-cis)-1-Methyl-2-(1-methylethenyl)cyclobutaneethanol
Additional Names: cis-(+)-2-isopropenyl-1-methylcyclobutaneethanol; (+)-(1R,2S)-1-(2¢-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane
Molecular Formula: C10H18O
Molecular Weight: 154.25
Percent Composition: C 77.87%, H 11.76%, O 10.37%
Literature References: Major component of grandlure, the sex pheromone of the boll weevil (Anthonomus grandis, Boheman). Isoln and synthesis: J. H. Tumlinson et al., Science 166, 1010 (1969); eidem, J. Org. Chem. 36, 2616 (1971). Synthesis of optically active grandisol: P. D. Hobbs, P. D. Magnus, Chem. Commun. 1974, 856; eidem, J. Am. Chem. Soc. 98, 4594 (1976); K. Mori, Tetrahedron 34, 915 (1978); of enantiomerically pure grandisol: J. B. Jones et al., Can. J. Chem. 60, 2007 (1982). Synthesis of racemate: B. M. Trost et al., J. Am. Chem. Soc. 99, 3088 (1977). Short stereoselective synthesis of (±)-grandisol: I. Aljancic-Solaja et al., Helv. Chim. Acta 70, 1302 (1987). Review of syntheses: J. A. Katzenellenbogen, Science 194, 139-148 (1976); J. M. Brand et al., Fortschr. Chem. Org. Naturst. 37, 18-29 (1979), see also refs pp 157-190; K. Mori, "The Synthesis of Insect Pheromones" in The Total Synthesis of Natural Products vol. 4, J. ApSimon, Ed. (Wiley-Interscience, New York, 1981) pp 80-85.
Properties: Liquid, bp1.0 50-60°. [a]D21.5 +18.5° (c = 1 in hexane). nD20 1.4748.
Boiling point: bp1.0 50-60°
Optical Rotation: [a]D21.5 +18.5° (c = 1 in hexane)
Index of refraction: nD20 1.4748 |