(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester
- Product Name
- (7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester
- CAS No.
- 30809-15-5
- Chemical Name
- (7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester
- Synonyms
- Talbotine;(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester;Indolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12a(12H)-carboxylic acid, 9-ethylidene-5,6,7,7a,8,8a,9,10-octahydro-12-hydroxy-, methyl ester, (7aS,8aS,9E,12R,12aS)-
- CBNumber
- CB52255386
- Molecular Formula
- C21H24N2O4
- Formula Weight
- 368.43
- MOL File
- 30809-15-5.mol
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(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester Property
- Melting point:
- 212°C
- Boiling point:
- 576.0±50.0 °C(Predicted)
- Density
- 1.44±0.1 g/cm3(Predicted)
- pka
- 12.03±0.40(Predicted)
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(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester Chemical Properties,Usage,Production
Description
This alkaloid which has been obtained from the leaves of Pleiocarpa talbotii Wernham contains a secondary N(b) atom and a cyclic hemiacetal group. It is strongly laevorotatory having [α]>D - 200° (CHC13). A secondary hydroxyl group is present and the base forms an O-methyl ether, m.p. 155-6°C. The O,N-diacetyl derivative is also crystalline with m.p. 190-3°C. Catalytic hydrogena_x0002_tion leads to 19: 2D-dihydrota1botine. When treated with NaOMe and NaOH the alkaloid yields two products, a lactone and a hydroxymethy1 compound in which the hemiacetal ring is opened. These data, together with the infrared and NMR spectra, lead to the complete relative stereochemistry of the alkaloid.
References
Pinar et al., Helv. Chim. Acta, 54, 15 (1971)
(7aS,9E)-9-Ethylidene-5,6,7,7aα,8,8aα,9,10-octahydro-12β-hydroxyindolo[3,2,1-ij]pyrano[3,4-b][1,5]naphthyridine-12aα(12H)-carboxylic acid methyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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