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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

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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 Structure
(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)
pka9.26±0.28(Predicted)
Safety Information
MSDS Information
(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
DescriptionPresent 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.
ReferencesYamamura, 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
Tag:(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(4684-24-6) Related Product Information