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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

(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Struktur
478-13-7
CAS-Nr.
478-13-7
Englisch Name:
(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol
Synonyma:
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
Summenformel:
C20H21NO5
Molgewicht:
355.38
MOL-Datei:
478-13-7.mol

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

Schmelzpunkt:
188°C
Siedepunkt:
517.6±50.0 °C(Predicted)
Dichte
1.41±0.1 g/cm3(Predicted)
pka
13.38±0.20(Predicted)

Sicherheit

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

Beschreibung

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.

Einzelnachweise

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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


(13R,13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-13β-ol Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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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
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