(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine

CAS No.
23943-90-0
Chemical Name:
(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine
Synonyms
Bractavine;Orientalidine;(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine;1H,7H-[1,3]Benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine, 9,10,15b,16-tetrahydro-5,15-dimethoxy-, (15bS)- (9CI)
CBNumber:
CB62163525
Molecular Formula:
C22H23NO6
Molecular Weight:
397.42
MDL Number:
MOL File:
23943-90-0.mol
Last updated:2023-07-12 17:18:41

(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine Properties

Melting point 196-8°C
Boiling point 547.5±50.0 °C(Predicted)
Density 1.42±0.1 g/cm3(Predicted)
pka 6.02±0.20(Predicted)

(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine Chemical Properties,Uses,Production

Description

This alkaloid from Papaver orientale forms colourless crystals from AcOEt and has [α] 22 D- 254° ± 4° (c 0.31, MeOH). It forms a methiodide, m.p. 252-3°C, a methine, m.p. 195-7°C and dimethine, m.p. l46-8°C. Exhaustive methylation gives trimethylamine and a nitrogen-free oil as the final products. Oxidation of the alkaloid with chromic acid or KMn04 yields Alkaloid PO-4 (q.v.). When refluxed with 5 per cent H2S04 the base yields formaldehyde which may arise from either the hydrolysis of the methylenedioxy group or, more probably, that of the 1: 3-benzodioxan group.

References

Preininger et al., Collect. Czech. Chern. Cornrnun., 34,875 (1969)

(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine Preparation Products And Raw materials

Raw materials

Preparation Products

(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine Bractavine Orientalidine 1H,7H-[1,3]Benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine, 9,10,15b,16-tetrahydro-5,15-dimethoxy-, (15bS)- (9CI) 23943-90-0