4783. Hydrocinchonine
Nomenclature
CAS number: 485-65-4
(9S)-10,11-Dihydrocinchonan-9-ol; cinchotine; cinconifine; (+)-dihydrocinchonine; pseudocinchonine. C19H24N2O; mol wt 296.41.
C 76.99%, H 8.16%, N 9.45%, O 5.40%.
Description and references
From cinchona barks: Caventou, Willm, Compt. Rend. 69, 284 (1869). Prepn from cinchonine: Hesse, Ann. 300, 46 (1898); Pum, Monatsh. Chem. 16, 68 (1895); Arlt, ibid. 20, 426, 439 (1899); Heidelberger, Jacobs, J. Am. Chem. Soc. 41, 817 (1919). Structure: Rabe, Ber. 55, 522 (1922). Conversion of hydroquinidine to hydrocinchonine: King, J. Chem. Soc. 1946, 523. HPLC determn: C.-T. A. Chung, E. J. Staba, J. Chromatogr. 295, 276 (1984). 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.
Properties
Prisms, mp 268-269°. [α]D14 +204° (c = 0.6 in alc). Almost insol in water, ether. Sol in alcohol.Derivative
Hydrochloride.C19H24N2O.HCl; mol wt 332.87.
C 68.56%, H 7.57%, N 8.42%, O 4.81%, Cl 10.65%.