Title: Buphanamine
CAS Registry Number: 6793-24-4
CAS Name: (1a)-2,3-Didehydro-7-methoxycrinan-1-ol
Molecular Formula: C17H19NO4
Molecular Weight: 301.34
Percent Composition: C 67.76%, H 6.36%, N 4.65%, O 21.24%
Literature References: Isoln from bulb of Buphane (Boöphane) 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). [a]24589 -195°; [a]24436 -408° (c = 0.97); [a]D20 -205° (c = 0.69, 95% ethanol); [a]D21 -194° (c = 0.247, chloroform). uv max: 287 nm (e 1495).
Melting point: mp 183-185° (Fales); mp 192-194° (Goosen)
Optical Rotation: [a]24589 -195°; [a]24436 -408° (c = 0.97); [a]D20 -205° (c = 0.69, 95% ethanol); [a]D21 -194° (c = 0.247, chloroform)
Absorption maximum: uv max: 287 nm (e 1495)
Derivative Type: Hydrochloride
Molecular Formula: C17H19NO4.HCl
Molecular Weight: 337.80
Percent Composition: C 60.44%, H 5.97%, N 4.15%, O 18.95%, Cl 10.50%
Properties: Prisms from ethanol + ether, mp 180°.
Melting point: mp 180°
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