References of 7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one,1,3,4,6,7,13,14,14a-octahydro-, (7R,14R,14aR)-
Title: Anagyrine
CAS Registry Number: 486-89-5
CAS Name: [7
R-(7a,7ab,14a)]-7,7a,8,9,10,11,13,14-Octahydro-7,14-methano-4
H,6
H-dipyrido[1,2-
a:1¢,2¢-
e][1,5]diazocin-4-one
Synonyms: 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)