5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one

CAS No.
1167-58-4
Chemical Name:
5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one
Synonyms
Neronine;5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one;[1,3]Dioxolo[6,7][2]benzopyrano[3,4-g]indol-7(1H)-one, 2,3,5,5a,12b,12c-hexahydro-5-hydroxy-12-methoxy-1-methyl-, (5S,5aS,12bS,12cS)-
CBNumber:
CB42308238
Molecular Formula:
C18H19NO6
Molecular Weight:
345.34656
MDL Number:
MOL File:
1167-58-4.mol

5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one Properties

Melting point 196-7°C
Boiling point 558.7±50.0 °C(Predicted)
Density 1.49±0.1 g/cm3(Predicted)
pka 12.97±0.20(Predicted)

5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one Chemical Properties,Uses,Production

Description

This alkaloid possesses a similar structure to that of Nerinine (q.v.) and is found in Nerine krigeii. It may be crystallized from AcOEt and is dextrorotatory with [0:]54 + 161.6° (c 0.57, CHC13). It is hygroscopic and behaves as a monoacidic base yielding a picrate as yellow prisms, m.p. 205-9°C (dec.); a methiodide, m.p. 260-5°C (dec.) and a crystalline O-acetate, m.p. 20t-2°C. It contains a lactone ring which may be opened by alkalies and regenerated by acids.

References

Briggs et at., J. Arner. Chern. Soc., 78,2899 (1956)
Jeffs, Hawksworth., Tetrahedron Lett., 217 (1963)

5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one Preparation Products And Raw materials

Raw materials

Preparation Products

5α-Hydroxy-11-methoxy-1-methyl-9,10-(methylenebisoxy)lycorenan-7-one Neronine [1,3]Dioxolo[6,7][2]benzopyrano[3,4-g]indol-7(1H)-one, 2,3,5,5a,12b,12c-hexahydro-5-hydroxy-12-methoxy-1-methyl-, (5S,5aS,12bS,12cS)- 1167-58-4