(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
![(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 Structure](CAS/20180808/GIF/4684-24-6.gif)
- CAS No.
- 4684-24-6
- Chemical 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
- 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)-;(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
- CBNumber:
- CB12284375
- Molecular Formula:
- C17H27NO3
- Molecular Weight:
- 293.4
- MDL Number:
- 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,Uses,Production
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)