1492. Buphanamine
Nomenclature
CAS number: 6793-24-4
(1α)-2,3-Didehydro-7-methoxycrinan-1-ol. C17H19NO4; mol wt 301.34.
C 67.76%, H 6.36%, N 4.65%, O 21.24%.
Description and references
Isoln from bulb of Buphane (Bo"ophane) disticha Herb., Appleg. (Haemanthus toxicarius Herb.) Amaryllidaceae: Humber, Taylor, Can. J. Chem. 33, 1268 (1955); Hauth, Stauffacher, Helv. Chim. Acta 44, 491 (1961). From B. fischeri Baker: Renz et al., ibid. 38, 1209 (1955). Identity with “oily” haemanthine: Goosen, Warren, J. Chem. Soc. 1960, 1094. Structure and stereochemistry: Fales, Wildman, J. Org. Chem. 26, 881 (1961). Revised structure: Wildman in The Alkaloids vol. XI, R. H. F. Manske, Ed. (Academic Press, New York, 1968) p 361. NMR of revised structure: Crain et al., J. Am. Chem. Soc. 93, 990 (1971). High-resolution mass spectrum: P. Longevialle et al., Org. Mass Spectrom. 7, 401 (1973).
Properties
Prisms from ethyl acetate, mp 183-185° (Fales); from acetone, mp 192-194° (Goosen). [α]24589 -195°; [α]24436 -408° (c = 0.97); [α]D20 -205° (c = 0.69, 95% ethanol); [α]D21 -194° (c = 0.247, chloroform). uv max: 287 nm (ε 1495).Derivative
Hydrochloride.C17H19NO4.HCl; mol wt 337.80.
C 60.44%, H 5.97%, N 4.15%, O 18.95%, Cl 10.50%.