9106. Tecomanine
Nomenclature
CAS number: 6878-83-7
[4R-(4α,7β,7aβ)]-1,2,3,4,7,7a-Hexahydro-2,4,7-trimethyl-6H-2-pyrindin-6-one; tecomine. C11H17NO; mol wt 179.26.
C 73.70%, H 9.56%, N 7.81%, O 8.93%.
Description and references
Principal alkaloid isolated from Tecoma stans (L.) H.B.K. (Bignonia stans L.), Bignoniaceae: Y. Hammouda, M. M. Motawi, Egypt. Pharm. Bull. 41, 73 (1959), C.A. 54, 21646c (1960). Structure: G. Jones et al., Tetrahedron Lett. 1963, 397. Stereochemistry, abs config and crystal structure: G. Jones et al., Chem. Commun. 1971, 994; G. Ferguson, W. C. Marsh, J. Chem. Soc. Perkin Trans. 2 1975, 1124. Hypoglycemic activity of salts: Y. Hammouda et al., J. Pharm. Pharmacol. 16, 833 (1964); Y. Hammouda, M. S. Amer, J. Pharm. Sci. 55, 1452 (1966). Stereoselective total synthesis of (±)-form: T. Imanishi et al., Tetrahedron Lett. 22, 667 (1981). Facile synthesis of (+)-form: T. Kametani et al., Heterocycles 26, 1491 (1987).
Properties
Liquid. bp0.1 125°. [α]D24 -175° (c = 1.17 in CHCl3). uv max (alc): 226 nm (log ε 4.10).Derivative
Methiodide.C12H20INO; mol wt 321.20.
C 44.87%, H 6.28%, I 39.51%, N 4.36%, O 4.98%.
Properties
Crystals, dec 240-242°.Derivative
Methoperchlorate.C12H20ClNO5; mol wt 293.74.
C 49.07%, H 6.86%, Cl 12.07%, N 4.77%, O 27.23%.