|
|
| | Repanduline Basic information |
| Product Name: | Repanduline | | Synonyms: | Repanduline;(1S,1'R,8S)-6-Methoxy-2,2'-dimethyl-12,13-[methylenebis(oxy)]-8,6'-(methyleneoxy)berbaman-7(8H)-one;10H,20H,23H-16,19a-Epoxy-6,9-etheno-4,27:14,17-dimetheno-19H-1,3-dioxolo[9,10]pyrido[2',3':18,19][1,12]dioxacyclodocosino[3,4,5-ij]isoquinolin-20-one, 10a,11,12,13,24,25,25a,26-octahydro-21-methoxy-11,25-dimethyl-, (10aS,19aS,25aR)- | | CAS: | 20398-02-1 | | MF: | C37H36N2O7 | | MW: | 620.7 | | EINECS: | | | Product Categories: | | | Mol File: | 20398-02-1.mol |  |
| | Repanduline Chemical Properties |
| Melting point | 2l5-232°C | | density | 1.42±0.1 g/cm3(Predicted) | | pka | 7.63±0.40(Predicted) |
| | Repanduline Usage And Synthesis |
| Description | A bisbenzylisoquinoline type alkaloid present in Daphnandra Dielsii Perkins and
D. repandula, the original formula of C4oH460sN2 was altered to C37H3407N2
and finally to that given above. When purified by recrystallization from MeOH
it forms slender yellow needles which darken and shrink,at 180-5°C and then
decompose over the rather wide temperature range given above. The base is
dextrorotatory with [α]16D + 434° (c 0.2, MeOH) or [α]27D + 473° (c 0.98,
CHCI 3). A methoxyl group, a methylenedioxy group, two methylimino groups
and a double ether bridge are present. The dihydrochloride yields yellow prisms
from H20, decomposing at 100°C; the dioxalate, crystallizing from MeOH as
yellow tetrahedra, decomposes at 214° C and the dimethiodide, decomposes at
240° C. The structure has been established from the NMR and mass spectra. | | References | Bick, Whalley., Unir. Queensland Papers, Dept. Chern., 1, No. 28 (1946)
Bick, Whalley., ibid, 1, No. 30 (1947)
Bick et al., J. Chern. Soc., 692 (1953)
Harley-Mason et al., J. Chern. Soc., C, 1948 (1967)
Spectra:
Bicketal., J. Chern. Soc., C. 1951 (1967) |
| | Repanduline Preparation Products And Raw materials |
|