Vinburnine

Base Information

• Chemical Name: Vinburnine
• CAS No.: 4880-88-0
• Deprecated CAS: 6880-38-2,13090-13-6,412037-03-7
• Molecular Formula: C19H22N2O
• Molecular Weight: 294.396
• Hs Code.: 2933990090
• European Community (EC) Number: 225-490-5
• NSC Number: 322920
• UNII: G54D0HMY25,64UB2942IE
• DSSTox Substance ID: DTXSID6045119
• Nikkaji Number: J12.783C
• Wikipedia: Vinburnine
• Wikidata: Q2526386
• NCI Thesaurus Code: C152880
• Pharos Ligand ID: UK3BXKZBAR6L
• Metabolomics Workbench ID: 67853
• ChEMBL ID: CHEMBL1892145
• Mol file: 4880-88-0.mol

Synonyms:(-)-eburnamonine;Cervoxan;eburnamonine;eburnamonine monohydrochloride, (3alpha,16alpha)-isomer;eburnamonine phosphate, (3alpha,16alpha)-isomer;eburnamonine, (3alpha,16alpha)-isomer;vinburnine

Chemical Property of Vinburnine

Chemical Property:

• Appearance/Colour: White to slightly yellow crystalline powder
• Vapor Pressure: 5.25E-08mmHg at 25°C
• Melting Point: 174-177 °C(lit.)
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 441.9 °C at 760 mmHg
• PKA: 8.13±0.40(Predicted)
• Flash Point: 221 °C
• PSA: 25.24000
• Density: 1.34 g/cm³
• LogP: 3.71250
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 294.173213330
• Heavy Atom Count: 22
• Complexity: 492

Purity/Quality:

99% ^*data from raw suppliers

(-)-Eburnamonine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2
• Isomeric SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=O)C2
• Uses: Cerebral vasodilatator (-)-Eburnamonine shows protective effects on mice from the lethal consequences of hypoxia.
• Therapeutic Function: Cerebrotonic

Technology Process of Vinburnine

There total 162 articles about Vinburnine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(+) eburnamenine (517-30-6) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0)

Guidance literature:

(+) eburnamenine; With hydrogenchloride; In water; at 20 ℃; for 4h; Inert atmosphere;

With pyridinium dichromate; In dichloromethane; water; for 0.5h; Inert atmosphere;

DOI:10.1016/j.chempr.2017.04.007

Reference yield: 84.0%

3-((1R,12bR)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid methyl ester (86708-31-8) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0)

Guidance literature:

With sodium hydroxide; In water; ethylene glycol; at 155 - 160 ℃; for 3h;

Reference yield: 62.0%

C20H25N2O2(1+)*ClO4(1-) → (-)-eburnamonine (2580-88-3,4880-88-0,53494-54-5,60384-17-0,71697-48-8,474-00-0) + (–)-20-epi-eburnamonine (71697-48-8)

Guidance literature:

C₂₀H₂₅N₂O₂⁽¹⁺⁾*ClO₄^(1-); With palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide; at 23 ℃; for 3.5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 23 ℃; for 3h;

DOI:10.1002/anie.202106184

upstream raw materials:

19-oxoeburnamonine

(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime

(-)-14-imino-eburnan

(3aS,10bR,12bS)-3a-Ethyl-5-nitro-2,3,3a,4,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene

Downstream raw materials:

(6S)-6-hydroxyeburnamonine

(6R)-6-hydroxyeburnamonine

eburnamine

(15S,17S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2,4,6,8⁽¹⁸⁾-tetraen-17-ol

Refernces

• 1、 Lewin, G.,Poisson, J.,Toffoli, P.. "NITROINDOLENINES EN SERIE VINCADIFFORMINE : INTERMEDIAIRES D'ACCES A LA VINCAMONE ET A UN SQUELETTE AZAHOMOASPIDOSPERMANE". . p. 493 - 500. Retrieved 1987.
• 2、 -. "Intermediate, preparation method and application of intermediate in synthesis of vincamine". Paragraph 0139-0143. . Retrieved 2021/09/01.
• 3、 Liang, Lixin,Zhou, Shiqiang,Zhang, Wei,Tong, Rongbiao. "Catalytic Asymmetric Alkynylation of 3,4-Dihydro-β-carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids". . p. 25135 - 25142. Retrieved 2021/10/23.