Vellosimine

Base Information

• Chemical Name: Vellosimine
• CAS No.: 6874-98-2
• Molecular Formula: C₁₉H₂₀N₂O
• Molecular Weight: 292.381
• UNII: 04956U0JGH
• DSSTox Substance ID: DTXSID701318281
• Wikidata: Q27102794
• Mol file: 6874-98-2.mol

Synonyms:(+)-vellosimine;vellosimine

Chemical Property of Vellosimine

Chemical Property:

• Vapor Pressure: 1.1E-09mmHg at 25°C
• Melting Point: 305-306°
• Refractive Index: 1.6140 (estimate)
• Boiling Point: 488.3°Cat760mmHg
• PKA: 17.62±0.40(Predicted)
• Flash Point: 249.1°C
• PSA: 36.10000
• Density: 1.29g/cm³
• LogP: 3.16850
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 292.157563266
• Heavy Atom Count: 22
• Complexity: 516

Purity/Quality:

>=95% ^*data from raw suppliers

Vellosimine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2C3CC1C(C2CC4=C3NC5=CC=CC=C45)C=O
• Isomeric SMILES: C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@H]2CC4=C3NC5=CC=CC=C45)C=O

Technology Process of Vellosimine

There total 35 articles about Vellosimine 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: 58.0%

(3E,6S,9aS)-3-ethylidene-1-(methoxymethylene)hexahydro-1H-2,6-methanoquinolizin-7(2H)-one + phenylhydrazine (100-63-0) → (+)-vellosimine (6874-98-2,88199-28-4,124096-80-6)

Guidance literature:

(3E,6S,9aS)-3-ethylidene-1-(methoxymethylene)hexahydro-1H-2,6-methanoquinolizin-7(2H)-one; phenylhydrazine; In ethanol; for 6h; Inert atmosphere; Reflux;

With hydrogenchloride; acetyl chloride; In ethanol; for 2h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201407280

Reference yield: 55.0%

(2S,6S,13S)-3-Eth-(E)-ylidene-13-formyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine-13-carboxylic acid methyl ester (2520-44-7,92218-35-4) → vellosimine (6874-98-2,88199-28-4,124096-80-6)

Guidance literature:

With hydrogenchloride; potassium hydroxide; 1) 30 deg C, 6 hr, 2) water bath, 90 deg C, 10 min;

Reference yield: 30.0%

(6S,10S)-(-)-9-formyl-12-((Z)-2'-iodo-2'-butenyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cycloocta[b]indole (288141-11-7) → (+)-3-ethylidene-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methanoindolo[2,3-a]quinolizine-13-carboxaldehyde (6874-98-2) + 16-epi-koumidine aldehyde

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 8h; Heating;

DOI:10.1021/jo030006h

upstream raw materials:

16-epi-vellosimine

phenylhydrazine

(2R,6S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-3-eth-(Z)-ylidene-1,3,4,7,8,13b-hexahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole

Ajmaline

Downstream raw materials:

10-de oxy-sarpagine

vinorine

(+)-vellosimine

Sarpagine

Refernces

• 1、 Krüger, Sebastian,Gaich, Tanja. "Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids-A generalized approach". supporting information. p. 315 - 317. Retrieved 2015/09/21.
• 2、 Yin, Wenyuan,Kabir, M. Shahjahan,Wang, Zhijian,Rallapalli, Sundari K.,Ma, Jun,Cook, James M.. "Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and Macusine A". scheme or table. p. 3339 - 3349. Retrieved 2010/07/13.