4201-84-7

Basic information

• Product Name: Isoeburnamine
• Synonyms: 14,15-Dihydroeburnamenin-14β-ol
• CAS NO: 4201-84-7
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.40666
• Mol File: 4201-84-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Isoeburnamine(CAS DataBase Reference)
• NIST Chemistry Reference: Isoeburnamine(4201-84-7)
• EPA Substance Registry System: Isoeburnamine(4201-84-7)

Safety Data

• Hazardous Substances Data: 4201-84-7(Hazardous Substances Data)

Upstream product

• 64585-83-7 (+/-)-Eburnamonine lactam 
• 62926-56-1 (1S,12bS)-1-[1,3]Dithian-2-ylmethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine; hydrochloride 
• 1354568-46-9 (S)-2-allyl-2-ethyl-N-benzoyl-δ-valerolactam 
• 199190-53-9 3-(3-Ethyl-2-oxo-tetrahydro-furan-3-yl)-propionic acid 
• 111154-20-2 3-Ethyl-5-hydroxy-3-(3-hydroxy-propyl)-dihydro-furan-2-one 
• 111154-23-5 3-(3-Ethyl-2-methoxy-tetrahydro-furan-3-yl)-propionic acid 
• 102631-76-5 3-Ethyl-3-((E)-2-nitro-vinyl)-tetrahydro-pyran-2-one 

Downstream Products

• 1617-90-9 vincamin 
• 65026-49-5 (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2,4,6,8⁽¹⁸⁾-tetraene 
• 4880-88-0 vinburnine 
• 2580-88-3 (-)-eburnamonine 

Relevant articles and documents

Intermediate and preparation method and application thereof in synthesis of vinorchine

The invention relates to the technical field of chemical drug synthesis, and discloses an application of an intermediate or a preparation method thereof in synthesis of vinorchin, adopts a modular synthetic strategy, adopts the compound D with 1 ring structures and C20 quaternary carbon centers, 5 (i.e. the compound 5) as a synthesis building block. The operation is simple and reaction conditions are easy for large-scale amplification effect.

Synthesis of eburnamine, isoeburnamine, and eburnamonine via a spirocyclic intermediate

Racemic eburnamonine (1) was synthesized via 6, an intermediate possessing local symmetry. Cleavage of the cyclopentene subunit led to pentacyclic aldehydes 8a/8b which on subsequent borohydride and Wolff-Kishner reductions gave 12. The final steps included a RuCl3-catalyzed periodate oxidation and pyridinium chlorochromate (PCC) oxidation. The penultimate intermediates were racemic eburnamine (2) and racemic isoeburnamine (3).

STRUCTURE OF GONIOMITINE, A NEW TYPE OF INDOLE ALKALOID

The structure 1 proposed for goniomitine, an indole alkaloid isolated from the root bark of Gonioma malagasy (Apocynaceae), was inferred from an analysis of its MS, 1H and 13C NMR spectral data.A biogenetic scheme is proposed to account for the formation of 1 from vincadifformine 9.