(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol

(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol structure

CAS No.: 478-13-7

Chemical Name:: (13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol

Synonyms: Ophiocarpine;l-Ophiocarpine;9,10-Dimethoxy-2,3-(methylenedioxy)-13aα-berbin-13β-ol;(13R)-5,8,13,13aα-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-ol;(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol;6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-ol, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13R,13aR)-

CBNumber:: CB82346698

Molecular Formula:: C20H21NO5

Molecular Weight:: 355.38

MDL Number:: MFCD01732406

MOL File:: 478-13-7.mol

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(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Properties

Melting point	188°C
Boiling point	517.6±50.0 °C(Predicted)
Density	1.41±0.1 g/cm3(Predicted)
pka	13.38±0.20(Predicted)

(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Chemical Properties,Uses,Production

Description

This protoberberine alkaloid is the major constituent of Corydalis ophiocarpa Hook. It has [α] ²⁴ _D - 284° (CHC13) and yields a sparingly soluble hydrochloride; a methiodide, m.p. 271°C (dec.) and the O-acetate, m.p. l41-3°C (165-7°C). It contains two methoxyl groups and one methylenedioxy group and when boiled with HCl furnishes a yellow base which, on oxidation with iodine and subsequent reduction, is converted into (±)-Canadine (q.v.). The alkaloid is therefore 13- hydroxycanadine, a structure confirmed by its oxidation to 6:7-methylenedioxy_x0002_l-keto-1: 2: 3 :4-tetrahydroisoquinoline (noroxyhydrastinine), m.p. 183°C, with KMn04' The optically inactive form crystallizes as colourless needles from MeOH-CHC13 , m.p. 252°C and also gives an O-acetate as needles from petroleum ether, m.p. 172-4°C.

References

Manske., Can. J. Res., 17B, 51 (1939)
Govindachari, Rajaduvai., J. Chern. Soc., 557 (1957)
Ohta, Toni, Morozumi., Tetrahedron Lett., 859 (1963)

(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Preparation Products And Raw materials

Raw materials

Preparation Products

(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Suppliers

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(13R)-5,8,13,13aα-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-ol (13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol 9,10-Dimethoxy-2,3-(methylenedioxy)-13aα-berbin-13β-ol Ophiocarpine l-Ophiocarpine 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13-ol, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13R,13aR)- 478-13-7