Virosecurinine

Base Information

• Chemical Name: Virosecurinine
• CAS No.: 884-68-4
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• NSC Number: 326131,107415,107414,107413
• DSSTox Substance ID: DTXSID00859919
• Wikidata: Q104396460
• Metabolomics Workbench ID: 125839
• ChEMBL ID: CHEMBL1965517
• Mol file: 884-68-4.mol

Synonyms:viro-securinine;viroallosecurinine;virosecurinine

Chemical Property of Virosecurinine

Chemical Property:

• Melting Point: 136-138 °C
• Boiling Point: 459.0±45.0 °C(Predicted)
• PKA: 8.29±0.20(Predicted)
• PSA: 29.54000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 1.34290
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 426

Purity/Quality:

98.5% ^*data from raw suppliers

Allosecurinine 98.43% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2C(C1)C34CC2C=CC3=CC(=O)O4

Technology Process of Virosecurinine

There total 35 articles about Virosecurinine 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: 93.0%

secu’amamine E (1203454-02-7) → Phyllochrysin (884-68-4)

Guidance literature:

With dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/acs.orglett.6b03716

Reference yield: 87.0%

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene (651738-07-7) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene; With trifluoroacetic acid; at 20 ℃; for 0.25h;

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ol0361251

Reference yield: 82.0%

(1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one (1126784-60-8) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate; In N,N-dimethyl acetamide; at 100 ℃; for 12h;

DOI:10.1039/b816576a

upstream raw materials:

(2α)-14ξ-hydroxy-14,15-dihydro-securinan-11-one

tert-butyl (S)-2-((6R,7aS)-6-((tert-butyldiphenylsilyl)oxy)-2-oxo-6,7-dihydrobenzofuran-7a(2H)-yl)piperidine-1-carboxylate

secu’amamine E

1-(tert-butyl) 2-methyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-5-oxopyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Wehlauch, Robin,Grendelmeier, Simone M.,Miyatake-Ondozabal, Hideki,Sandtorv, Alexander H.,Scherer, Manuel,Gademann, Karl. "Investigating Biogenetic Hypotheses of the Securinega Alkaloids: Enantioselective Total Syntheses of Secu'amamine E/ent-Virosine A and Bubbialine". . p. 548 - 551. Retrieved 2017/02/10.
• 2、 Gonzalez-Galvez, David,Garcia-Garcia, Elena,Alibes, Ramon,Bayon, Pau,De March, Pedro,Figueredo, Marta,Font, Josep. "Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine". experimental part. p. 6199 - 6211. Retrieved 2010/01/06.