473-99-4

Basic information

• Product Name: Eburnamine
• Synonyms: Eburnamine;(-)-14,15-Dihydroeburnamenine-14α-ol;(+)-Isoeburnamine;14,15-Dihydroeburnamenine-14α-ol
• CAS NO: 473-99-4
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.41
• Mol File: 473-99-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 484.4°Cat760mmHg
• Flash Point: 246.8°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 3.39E-10mmHg at 25°C
• Refractive Index: 1.718
• CAS DataBase Reference: Eburnamine(CAS DataBase Reference)
• NIST Chemistry Reference: Eburnamine(473-99-4)
• EPA Substance Registry System: Eburnamine(473-99-4)

Safety Data

• Hazardous Substances Data: 473-99-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H24N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,16,18,22H,2,5,8-12H2,1H3/t16-,18-,19+/m0/s1

Upstream product

• 138615-18-6 (16α)-14,15-dihydroeburnamenine-14,21-diol 
• 2580-88-3 (+/-)-Eburnamonine 
• 106375-27-3 3β-chloro-2β-hydroxy-1-<(p-methoxyphenyl)sulfonyl>aspidospermidin-8-one 
• 106367-82-2 3,3-dichloro-1,2-dehydroaspidospermidin-8-one 
• 64585-83-7 (+/-)-Eburnamonine lactam 
• 119459-52-8 (1RS,12bRS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-ethanol 
• 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 

Downstream Products

• 4880-88-0 vinburnine 
• 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 
• 1617-90-9 vincamin 
• 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).

Expeditious enantioselective syntheses of indole alkaloids of Aspidosperma- and Hunteria-type

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