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| (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione Basic information |
Product Name: | (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione | Synonyms: | (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione;Nobiline;2,5-Methano-2H-cyclopent[d]oxepin-1,4-dione, 8-[(dimethylamino)methyl]hexahydro-8a-methyl-9-(1-methylethyl)-, (2R,5R,5aS,8S,8aR,9S)- | CAS: | 4684-24-6 | MF: | C17H27NO3 | MW: | 293.4 | EINECS: | | Product Categories: | | Mol File: | 4684-24-6.mol | |
| (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione Chemical Properties |
Melting point | 87-8°C | Boiling point | 421.7±20.0 °C(Predicted) | density | 1.089±0.06 g/cm3(Predicted) | pka | 9.26±0.28(Predicted) |
| (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione Usage And Synthesis |
Description | Present in Dendrobiurn nobile, this alkaloid forms colourless crystals from
MeOH. It yields a crystalline hydrochloride, m.p. 206-8°C and the methiodide,
m.p. 275-6°C. Treatment of the free base with alcoholic KOH followed by HCI
gives isonobiline hydrochloride, m.p. l83-5°C. LiAIH4 furnishes an amorphous
tril whereas NaBH4 in tetrahydrofuran gives the amorphous hydroxynobiline
which is converted into hydroxyisonobiline, m.p. 217 -9°C under the same
conditions as given above for the alkaloid. Hofmann degradation of nobiline
methiodide yields trimethylamine and deaminonobiline, m.p. l79-183°C. The
structure given above for the alkaloid has been suggested on the basis of these
chemical reactions and spectroscopic evidence. | References | Yamamura, Hirata., Tetrahedron Lett., 79 (1964) |
| (1R,8aα,9S)-6β-[(Dimethylamino)methyl]-1,5a,6,7,8,8a-hexahydro-5aα-methyl-9-isopropyl-1,4α-methano-2H-cyclopent[d]oxepine-2,5(4H)-dione Preparation Products And Raw materials |
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