Virosecurinine

Base Information

• Chemical Name: Virosecurinine
• CAS No.: 1857-30-3
• 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: 1857-30-3.mol

Synonyms:viro-securinine;viroallosecurinine;virosecurinine

Chemical Property of Virosecurinine

Chemical Property:

• Melting Point: 145-147℃ (hexane acetone )
• Boiling Point: 459°Cat760mmHg
• PKA: 8.29±0.20(Predicted)
• Flash Point: 197°C
• PSA: 29.54000
• Density: 1.3g/cm³
• 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% ^*data from raw suppliers

Viroallosecurinine ≥98% ^*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 39 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: 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: 87.0%

(+)-(5S,10aR,10bR,12S)-virosine A → viroallosecurinine (1857-30-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201903122

Reference yield: 87.0%

2-(6-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine-1-carboxylic acid tert-butyl ester (735315-23-8) → viroallosecurinine (1857-30-3)

Guidance literature:

2-(6-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine-1-carboxylic acid tert-butyl ester; With trifluoroacetic acid; at 20 ℃;

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.031

upstream raw materials:

(RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene

tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate

tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate

Refernces

• 1、 Honda, Toshio,Namiki, Hidenori,Kaneda, Kyosuke,Mizutani, Hirotake. "First Diastereoselective Chiral Synthesis of (-)-Securinine". . p. 87 - 89. Retrieved 2004.
• 2、 Dhudshia, Bhartesh,Cooper, Benjamin F. T.,MacDonald, Charles L. B.,Thadani, Avinash N.. "The asymmetric total synthesis of (-)-securinine". . p. 463 - 465. Retrieved 2009.
• 3、 Antien, Kevin,Cossío, Fernando P.,Deffieux, Denis,Lacambra, Aitor,Massip, Stéphane,Peixoto, Philippe A.,Pouységu, Laurent,Quideau, Stéphane. "Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A". . . Retrieved 2019/08/21.
• 4、 Bardaji, Gisela G.,Canto, Mariona,Alibes, Ramon,Bayon, Pau,Busque, Felix,De March, Pedro,Figueredo, Marta,Font, Josep. "Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide". experimental part. p. 7657 - 7662. Retrieved 2009/04/11.