Anagyrine

Title: Anagyrine
CAS Registry Number: 486-89-5
CAS Name: [7R-(7a,7ab,14a)]-7,7a,8,9,10,11,13,14-Octahydro-7,14-methano-4H,6H-dipyrido[1,2-a:1¢,2¢-e][1,5]diazocin-4-one
Additional Names: monolupine; rhombinin
Molecular Formula: C15H20N2O
Molecular Weight: 244.33
Percent Composition: C 73.74%, H 8.25%, N 11.47%, O 6.55%
Literature 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°. [a]D25 -168° (c = 4.8 in ethanol). Sol in water, alcohol, chloroform; slightly sol in ether, benzene.
Boiling point: bp4 210-215°; bp12 260-270°
Optical Rotation: [a]D25 -168° (c = 4.8 in ethanol)
Derivative Type: Hydrochloride trihydrate
Molecular Formula: C15H21ClN2O.3H2O
Molecular Weight: 334.84
Percent Composition: C 53.80%, H 8.13%, Cl 10.59%, N 8.37%, O 19.11%
Properties: Crystals, mp 235-236° (mp 296° when dry). [a]D25 -142.5° (c = 5). Freely sol in water.
Melting point: mp 235-236°; mp 296° when dry
Optical Rotation: [a]D25 -142.5° (c = 5)
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