uleine
- CAS No.
- 517-81-7
- Chemical Name:
- uleine
- Synonyms
- uleine;(12S)-2-Methyl-6-methylene-12-ethyl-1β,5β-methano-2,3,4,5,6,7-hexahydro-1H-azocino[4,3-b]indole;[12S,(+)]-12-Ethyl-2,3,4,5,6,7-hexahydro-2-methyl-6-methylene-1β,5β-methano-1H-azocino[4,3-b]indole;1,5-Methano-1H-azocino[4,3-b]indole, 12-ethyl-2,3,4,5,6,7-hexahydro-2-methyl-6-methylene-, (1R,5S,12S)-
- CBNumber:
- CB71334699
- Molecular Formula:
- C18H22N2
- Molecular Weight:
- 266.38
- MDL Number:
- MOL File:
- 517-81-7.mol
uleine Chemical Properties,Uses,Production
Description
An Aspidosperma alkaloid, this base occurs in several members of this species and particularly in A. ulei. It forms colourless crystals having the double melting point given above. It is slightly dextrorotatory with [α]25D + 11.5° (CHCI3 ) and gives an ultraviolet spectrum having a broad absorption maximum at 307-8 Mu.1 and a second maximum at 316 IT1J.1. The hydrochloride is crystalline with m.p. 241-2°C and the tnethiodide has m.p. 204-6°C. Oxidation with KMn04 yields formaldehyde indicative of an exocyc1ic methylene group.
References
Schmutz, Hunziker, Hirt., Helv. Chim. Acta, 40, 1189 (1957)
Schmutz, Hunziker, Hirt., ibid, 41, 288 (1958)
Buchi, Warnhoff.,J. Amer. Chem. Soc., 81,4433 (1959)
Ondetti, Deulofeu., Tetrahedron Lett., No.7, 1 (1959)
Synthesis:
Wilson et ai., Chem. Commun., 584 (1968)
