(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol

CAS No.
18269-16-4
Chemical Name:
(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol
Synonyms
Voaphylline hydroxyindolenine;Voaphylline hydroxyindolenine【neutral】;(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol;2H-3,13-Methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, (1aR,5aR,13S,13aS)-
CBNumber:
CB92199178
Molecular Formula:
C19H24N2O2
Molecular Weight:
312.41
MDL Number:
MOL File:
18269-16-4.mol

(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol Properties

Boiling point 478.8±45.0 °C(Predicted)
Density 1.38±0.1 g/cm3(Predicted)
pka 12.38±0.40(Predicted)

(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol Chemical Properties,Uses,Production

Description

This alkaloid from the leaf extract of Voacanga africana has the above structure in neutral or basic media as determined by spectral data, particularly the mass spectra. In acid solution it exists as the quaternary base. Reduction with KBH4 yields Voaphylline (q.v.) and conversely the base may be formed from the latter by oxidation with peracetic acid.

References

Kunesch, Das, Poisson., Bull. Soc. Chim. Fr., 3551 (1967)

(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol Preparation Products And Raw materials

Raw materials

Preparation Products

(1aR,5aR,13S,13aS)-13-Ethyl-4,5,11,12,13,13a-hexahydro-2H-3,13-methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol Voaphylline hydroxyindolenine Voaphylline hydroxyindolenine【neutral】 2H-3,13-Methanooxireno[9,10]azacycloundecino[5,4-b]indol-5a(1aH)-ol, 13-ethyl-4,5,11,12,13,13a-hexahydro-, (1aR,5aR,13S,13aS)- 18269-16-4