(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one

(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one structure

CAS No.: 16843-68-8

Chemical Name:: (4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one

Synonyms: Isocorymine;(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one;1H,3H,7H-6,11c-(Epoxymethano)-6a,11b-(iminoethano)pyrano[4,3-c]carbazol-12-one, 4-ethylidene-4,4a,5,6-tetrahydro-1-hydroxy-7,16-dimethyl-, (1R,4E,4aR,6S,6aS,11bS,11cR)-

CBNumber:: CB92241343

Molecular Formula:: C22H26N2O4

Molecular Weight:: 382.45

MDL Number:

MOL File:: 16843-68-8.mol

Last updated:2023-07-12 17:15:27

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(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one Properties

Melting point	l83-5°C
Boiling point	614.1±55.0 °C(Predicted)
Density	1.40±0.1 g/cm3(Predicted)
pka	12.00±0.20(Predicted)

(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one Chemical Properties,Uses,Production

Description

The alkaloidal extract of Hunteria urnbellata (K Schum) Stapf. may be treated chromatographically to yield this minor constituent which forms colourless crystals when purified from propanol. It is strongly laevorotatory with [α]_D - 243°. Two methylimino groups, a hydroxyl and a lactone ring are present. The base gives a crystalline O-acetate, m.p. 160°C. The original structure has been revised to that given above on the basis of NMR and mass spectra.

References

Bevan et al., Chern. Ind., 603 (1965) Revised structure: Bevan et al., Tetrahedron, 23,3809 (1967)

(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one Preparation Products And Raw materials

Raw materials

Preparation Products

(4E,4aS)-4-Ethylidene-4,4a,5,6-tetrahydro-1α-hydroxy-7,16-dimethyl-1H,3H,7H-6β,11cβ-(epoxymethano)-6aα,11bα-(iminoethano)pyrano[4,3-c]carbazol-12-one Isocorymine 1H,3H,7H-6,11c-(Epoxymethano)-6a,11b-(iminoethano)pyrano[4,3-c]carbazol-12-one, 4-ethylidene-4,4a,5,6-tetrahydro-1-hydroxy-7,16-dimethyl-, (1R,4E,4aR,6S,6aS,11bS,11cR)- 16843-68-8