(15S)-20,21-(Epoxyethano)-15-hydroxy-4-methyl-16-methyleneveatchane
- CAS No.
- 76-53-9
- Chemical Name:
- (15S)-20,21-(Epoxyethano)-15-hydroxy-4-methyl-16-methyleneveatchane
- Synonyms
- Veatchine;(15S)-20,21-(Epoxyethano)-15-hydroxy-4-methyl-16-methyleneveatchane;5H,13cH-8a,11-Methano-6,13b-propanocyclohept[h]oxazolo[2,3-a]isoquinolin-9-ol, dodecahydro-6-methyl-10-methylene-, (6R,6aR,8aR,9S,11R,13aR,13bS,13cS)- (9CI)
- CBNumber:
- CB32432808
- Molecular Formula:
- C22H33NO2
- Molecular Weight:
- 343.5
- MDL Number:
- MOL File:
- Mol file
| Melting point | 119-120° |
|---|---|
| alpha | D27.5 -69.01° (c = 1.06 in ethanol) |
| Boiling point | 482.2±45.0 °C(Predicted) |
| Density | 1.19±0.1 g/cm3(Predicted) |
| pka | 14.73±0.40(Predicted) |
| FDA UNII | I87Q3IZ7R5 |
(15S)-20,21-(Epoxyethano)-15-hydroxy-4-methyl-16-methyleneveatchane Chemical Properties,Uses,Production
Description
This alkaloid occurs in Garrya species and is a major constituent of G. veatchii. It is laevorotatory with [α]27.5D - 69.01°. The crystalline hydrochloride has m.p. 2Sl-2°C (dec.); hydrobromide, m.p. 229-2300 C and the hydriodide, m.p. 222-3°C (dec.). The O-acetate has m.p. l52-3°C and yields a hydrochloride, m.p. 258-9°C. The structure has been determined by chemical analysis and from spectroscopic data.
References
Wiesneretal., Can. J. Chem., 30,608 (1952)
Wiesner et al., Ber., 86,800 (1953)
Wiesner, Edwards., Experientia, 11,255 (1955)
Vorbrueggen, Djerassi., J. Amer. Chem. Soc., 84, 2999 (1962)
Nagata et al., ibid, 86,929 (1964)
Synthesis:
Valenta, Wiesner, Wong., Tetrahedron Lett., 2437 (1964)
Fujita, Fujita, Katayama., Tetrahedron, 26, 1009 (1970)
Wiesner et al., Experientia, 26, 471 (1970)