5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol

CAS No.
4850-04-8
Chemical Name:
5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol
Synonyms
Nudaurine;Amurinol I;5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol;Morphinan-7-ol, 5,6,8,14-tetradehydro-6-methoxy-17-methyl-2,3-[methylenebis(oxy)]-, (7β)- (9CI)
CBNumber:
CB92398326
Molecular Formula:
C19H21NO4
Molecular Weight:
327.37
MDL Number:
MOL File:
4850-04-8.mol

5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol Properties

Melting point 201-2°C
Boiling point 523.6±50.0 °C(Predicted)
Density 1.38±0.1 g/cm3(Predicted)
pka 12.41±0.40(Predicted)

5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol Chemical Properties,Uses,Production

Description

A morphine type alkaloid, this base is a minor constituent of the seeds of Papaver nudicaule var. amurense. It forms clusters of colourless crystals from Me2CO and has [α] 22 D - 52° (c 1.0, CHCI3). The salts are crystalline and include the hydriodide, m.p. 198°C (dec.); perchlorate, m.p. 188°C (dec.) and the picrate, m.p. 150°C (dec.). The structure given above has been determined on the basis of the infrared, NMR and mass spectra.

References

Boit, Flentje., Naturwiss., 47,180 (1960)
Flentje, Dopke, Jeffs., ibid, 52,259 (1965)
Dopke, Flentje, Jeffs., Tetrahedron, 24,4459 (1968)
Absolute configuration: Barton et ai., Chern. Ber., 100,2457 (1967)
Circular dichroism: Snatzke, Wollenberg.,!. Chern. Soc., C, 1581 (1966)

5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol Preparation Products And Raw materials

Raw materials

Preparation Products

5,6,8,14-Tetradehydro-6-methoxy-17-methyl-2,3-[methylenebisoxy]morphinan-7β-ol Amurinol I Nudaurine Morphinan-7-ol, 5,6,8,14-tetradehydro-6-methoxy-17-methyl-2,3-[methylenebis(oxy)]-, (7β)- (9CI) 4850-04-8