Lupinine
Title: Lupinine
CAS Registry Number: 486-70-4
CAS Name: [1R-trans]-Octahydro-2H-quinolizine-1-methanol
Additional Names: l-lupinine; (-)-lupinine
Molecular Formula: C10H19NO
Molecular Weight: 169.26
Percent Composition: C 70.96%, H 11.31%, N 8.28%, O 9.45%
Literature References: Naturally occurring l-form isolated from seeds and herb of Lupinus luteus L. and other L. species, Leguminosae also found in Anabasis aphylla L., Chenopodiaceae. Extraction procedure: J. F. Couch, J. Am. Chem. Soc. 56, 2434 (1934). Structure and synthesis: R. W. Willstätter, E. Fourneau, Ber. 35, 1910 (1902); P. Karrer et al., Helv. Chim. Acta 11, 1062 (1928); K. Winterfeld, F. W. Holschneider, Ber. 64B, 137, 692 (1931); K. Winterfeld, ibid. 692. Synthesis of racemic lupinine: F. W. Holschneider, K. Winterfeld, Arch. Pharm. 277, 192 (1939); G. C. Gerrans et al., Tetrahedron Lett. 1975, 4171; T. Iwashita et al., J. Org. Chem. 47, 230 (1982). Synthesis of racemic lupinine and epi-lupinine: G. R. Clemo et al., J. Chem. Soc. 1937, 965; H. Takahata et al., Chem. Pharm. Bull. 34, 4523 (1986); of l-epi-lupinine: M. L. Bremmer, S. M. Weinreb, Tetrahedron Lett. 24, 261 (1983). Absolute configuration of (-)-form: R. C. Cookson, Chem. Ind. (London) 1953, 339. Crystal structure: A. Koziol et al., Acta Crystallogr. B34, 3491 (1978). Biosynthesis: Soucek, Schutte, Angew. Chem. 74, 901 (1962); W. M. Golebiewski, I. D. Spenser, J. Am. Chem. Soc. 106, 1441 (1984).
Properties: Stout, orthorhombic prisms from acetone, mp 68.5-69.2°. bp4 160-164°; bp755 269-270°. [a]D26 -25.9° (c = 3 in water); [a]D28 -21° (c = 9.5 in alcohol). Sol in water, alcohol, chloroform, ether. It is a strong base.
Melting point: mp 68.5-69.2°
Boiling point: bp4 160-164°; bp755 269-270°
Optical Rotation: [a]D26 -25.9° (c = 3 in water); [a]D28 -21° (c = 9.5 in alcohol)
 
Derivative Type: l-Form hydrochloride
Molecular Formula: C10H20ClNO
Molecular Weight: 205.72
Percent Composition: C 58.38%, H 9.80%, Cl 17.23%, N 6.81%, O 7.78%
Properties: Orthorhombic prisms, mp 208-213°. [a]D -14°.
Melting point: mp 208-213°
Optical Rotation: [a]D -14°
 
Derivative Type: dl-Form
Properties: Crystals from acetone, mp 58.5-59.5°.
Melting point: mp 58.5-59.5°

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