9971. Vetivones
Description and references
Ketonic components of vetiver oil; from roots of Vetiveria zizanioides (Andropogon muricatus Retz., Gramineae). Two isomers, the α-form having the stronger odor. Isoln and structure: Pfau, Plattner, Helv. Chim. Acta 22, 640 (1939); Naves, Perrottet, ibid. 24, 3 (1941).
Derivative
α-Vetivone.Nomenclature
Description and references
Structure: Endo, DeMayo, Chem. Commun. 1967, 89; Marshall, Andersen, Tetrahedron Lett. 1967, 1611. Total syntheses of the racemate: Marshall et al., Chem. Commun. 1967, 753; Marshall, Warne, J. Org. Chem. 36, 178 (1971); Vandergen et al., Rec. Trav. Chim. 90, 1034, 1045 (1971); Dastur, J. Am. Chem. Soc. 96, 2605 (1974).
Properties
Crystals from pentane, strong agreeable odor. mp 51.5° (Naves, Perrottet); mp of racemate 30-35° (Marshall, Andersen). nD20 1.5384. [α]D20 +248° (chloroform). d420 1.003 (liquid, supercooled). uv max (ethanol): 233 nm (ε 13200).Derivative
β-Vetivone.Nomenclature
Description and references
Structure: Marshall et al., J. Am. Chem. Soc. 89, 2748, 2750 (1967). Syntheses of racemate: Marshall, Johnson, Chem. Commun. 1968, 391; eidem, J. Org. Chem. 35, 192 (1970); K. Uneyama et al., Chem. Lett. 1977, 493; S. Torii et al., Bull. Chem. Soc. Jpn. 51, 3590 (1978); E. Wenkert et al., J. Am. Chem. Soc. 100, 1267 (1978). Stereospecific synthesis of ()-β-vetivone: Deighton et al., Chem. Commun. 1975, 662; M. Asaoka et al., Chem. Lett. 1988, 1225.