623. Anagyrine
Nomenclature
CAS number: 486-89-5
(7R,14R,14aR)-1,3,4,6,7,13,14,14a-Octahydro-7,14-methano-2H,11H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-11-one; monolupine; rhombinin. C15H20N2O; mol wt 244.33.
C 73.74%, H 8.25%, N 11.47%, O 6.55%.
Description and references
Found in seeds of Anagyris foetida L., Leguminosae and in gorse (Ulex europaeus L., Leguminosae). Isoln: Ing, J. Chem. Soc. 1933, 504; Orekhov et al., Ber. 67, 1394 (1934); Couch, J. Am. Chem. Soc. 61, 3327 (1939); Briggs, Russell, J. Chem. Soc. 1942, 507; Galinsky, Stern, Ber. 77, 132 (1944); Faugeras, Ann. Pharm. Fr. 29, 241 (1971). Absolute configuration: Okuda et al., Chem. Ind. (London) 1961, 1116; Okuda et al., Chem. Pharm. Bull. 13, 491 (1965). Synthesis: van Tamelen, Baran, J. Am. Chem. Soc. 80, 4659 (1958); Goldberg, Lipkin, J. Org. Chem. 37, 1823 (1972).
Properties
Pale yellow glass. bp4 210-215°; bp12 260-270°. [α]D25 168° (c = 4.8 in ethanol). Sol in water, alcohol, chloroform; slightly sol in ether, benzene.Derivative
Hydrochloride trihydrate.C15H21ClN2O.3H2O; mol wt 334.84.
C 53.80%, H 8.13%, Cl 10.59%, N 8.37%, O 19.11%.