4-Benzyl-3-crotonyl-2-oxazolidinone

Base Information

• Chemical Name: 4-Benzyl-3-crotonyl-2-oxazolidinone
• CAS No.: 133812-16-5
• Molecular Formula: C14H15 N O3
• Molecular Weight: 245.278
• Mol file: 133812-16-5.mol

Synonyms:4-BCOX;4-benzyl-3-crotonyl-2-oxazolidinone

Chemical Property of 4-Benzyl-3-crotonyl-2-oxazolidinone

Chemical Property:

• Vapor Pressure: 4.22E-05mmHg at 25°C
• Melting Point: 84-88 °C(lit.)
• Boiling Point: 351°Cat760mmHg
• PKA: -1?+-.0.40(Predicted)
• Flash Point: 166.1°C
• PSA: 46.61000
• Density: 1.205g/cm³
• LogP: 2.09050
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (60 mg/ml)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 345

Purity/Quality:

97% ^*data from raw suppliers

CellSheetMigrationInhibitor,Locostatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC(=O)N1C(COC1=O)CC2=CC=CC=C2
• Isomeric SMILES: C/C=C/C(=O)N1C(COC1=O)CC2=CC=CC=C2
• Description: Locostatin (133812-16-5) inhibits cell migration by disrupting the interaction between Raf kinase inhibitor protein (RKIP) and Raf-1 kinase.1 Locostatin covalently binds to His86 of RKIP and also disrupts its interaction with G protein-coupled receptor kinase 2.2 Effectively inhibits cytokine release by human lymphocytes.3? Alleviates CCl4-induced liver fibrosis in a mouse model.4 A useful probe to explore the complex functions of RKIP in cell physiology.5
• Uses: Locostatin is a cell permeable, potent inhibitor of Raf kinase inhibitor protein (RKIP)/Raf1 kinase interaction and an inhibitor of cell migration

Technology Process of 4-Benzyl-3-crotonyl-2-oxazolidinone

There total 1 articles about 4-Benzyl-3-crotonyl-2-oxazolidinone 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: 89.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + crotonyl chloride (10487-71-5) → (S)-4-benzyl-N-butenoyloxazolidin-2-one (133812-16-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 3h;

Reference yield: 92.0%

2-iodo-propane (75-30-9) + (S)-4-benzyl-N-butenoyloxazolidin-2-one (133812-16-5) → (4S)-4-benzyl-3-(3-isopropylbutanoyl)oxazolidin-2-one

Guidance literature:

With indium(III) chloride; indium; copper(l) iodide; In water; at 20 ℃; for 24h; optical yield given as %de;

DOI:10.1016/j.tetlet.2008.12.079

Reference yield: 92.0%

(S)-4-benzyl-N-butenoyloxazolidin-2-one (133812-16-5) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + acenaphthene quinone (82-86-0) → (4S)-4-benzyl-3-((1R,1′S,2′S,6′R)-6′-hydroxy-1′-methyl-2-oxo-1′,2′,5′,6′,7′,7a′-hexahydro-2H-spiro[acenaphthylene-1,3′-pyrrolizine]-2′-carbonyl) oxazolidin-2-one

Guidance literature:

(S)-4-benzyl-N-butenoyloxazolidin-2-one; With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; In dichloromethane; at 20 ℃; for 0.166667h;

4R-4-hydroxyproline; acenaphthene quinone; In dichloromethane; at 20 ℃; regioselective reaction;

DOI:10.1039/c9ob01197h

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

crotonyl chloride

Downstream raw materials:

(4S)-4-benzyl-3-(3-cyclopentylbutanoyl)oxazolidin-2-one

(4S)-4-benzyl-3-(3-cyclohexylbutanoyl)oxazolidin-2-one

C₂₅H₂₉N₃O₆S

C₁₉H₂₁NO₃

Refernces