Title: Hydrocinchonidine
CAS Registry Number: 485-64-3
CAS Name: (8a,9R)-10,11-Dihydrocinchonan-9-ol
Additional Names: (-)-dihydrocinchonidine; cinchamidine
Molecular Formula: C19H24N2O
Molecular Weight: 296.41
Percent Composition: C 76.99%, H 8.16%, N 9.45%, O 5.40%
Literature References: Found in cinchona barks: Forst, Böhringer, Ber. 14, 1270 (1881); Hesse, ibid. 1683; idem, Ann. 214, 1 (1882); Skita, Nord, Ber. 45, 3312 (1912); Heidelberger, Jacobs, J. Am. Chem. Soc. 41, 817 (1919). Configuration: Ochiai et al., J. Pharm. Soc. Jpn. 67, 211 (1947). Stereospecific synthesis from secologanin: R. T. Brown, D. Curless, Tetrahedron Lett. 27, 6005 (1986). Total synthesis: M. Ihara et al., J. Chem. Soc. Perkin Trans. 1 1988, 1277. Stereoisomer of hydrocinchonine, q.v.
Properties: Needles or leaflets, mp 230°. [a]D15 -98° (alcohol). Practically insol in water. Sol in alcohol, chloroform; slightly sol in ether.
Melting point: mp 230°
Optical Rotation: [a]D15 -98° (alcohol) |