(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine

CAS No.
52659-54-8
Chemical Name:
(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine
Synonyms
Andrangine;(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine;2H-Cyclopent[ij]indolo[2,3-a]oxireno[g]quinolizine, 12a-ethyl-1a,4,5,5a,10,10b,11,12,12a,12b-decahydro-, (1aR,5aS,10aR,10bS,12aS,12bS)- (9CI)
CBNumber:
CB02319801
Molecular Formula:
C19H24N2O
Molecular Weight:
296.41
MDL Number:
MOL File:
52659-54-8.mol

(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine Properties

Melting point 132°C

(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine Chemical Properties,Uses,Production

Description

One of two alkaloids isolated from the leaves of Craspidospermum verticilliatum var. petiotare, this base also occurs in the leaves of Crioceras diptadeniij1oris. It yields colourless needles when crystallized from hexane and is laevorotatory with a specific rotation of [α]20D- 42° (c 1.0, CHC13). The ultraviolet spectrum in EtOH consists of two absorption maxima at 248 and 299 nm. The base has been characterized as the N-methyl derivative with m.p. 138°C and [α]20D + 60.5° (c 0.9, CHC13). The structure given has been established from chemical degradations and spectroscopic investigations.

References

Bruneton, Bouquet, Cave, Phytochem., 13, 1963 (1974)
Kan-Fan et at., Bull. Soc. Chim. Fr. (12 part 2), 2839 (1974)

(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine Preparation Products And Raw materials

Raw materials

Preparation Products

(2β,5α,12β,19α)-1-Demethyl-6β,7β-epoxyvallesamidine Andrangine 2H-Cyclopent[ij]indolo[2,3-a]oxireno[g]quinolizine, 12a-ethyl-1a,4,5,5a,10,10b,11,12,12a,12b-decahydro-, (1aR,5aS,10aR,10bS,12aS,12bS)- (9CI) 52659-54-8