Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl-

Base Information

• Chemical Name: Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl-
• CAS No.: 189169-55-9
• Molecular Formula: C27H22NOP
• Molecular Weight: 407.452
• DSSTox Substance ID: DTXSID20400664
• Nikkaji Number: J752.769A
• Mol file: 189169-55-9.mol

Synonyms:Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl-;189169-55-9;SCHEMBL4092628;DTXSID20400664;2-[2-(Diphenylphosphino)phenyl]-4-phenyl-2-oxazoline

Chemical Property of Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl-

Chemical Property:

• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 407.143901323
• Heavy Atom Count: 30
• Complexity: 541

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N=C(O1)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl-

There total 2 articles about Oxazole, 2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-phenyl- 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: 53.0%

2-(2-bromophenyl)-4-phenyl-4,5-dihydrooxazole (153233-81-9,191330-82-2) + diphenylphosphane (829-85-6) → 2-[2'-(diphenylphosphanyl)phenyl]-4-phenyl-4,5-dihydrooxazole (189169-55-9)

Guidance literature:

diphenylphosphane; With copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 20 ℃; for 0.333333h; Schlenk technique; Inert atmosphere;

2-(2-bromophenyl)-4-phenyl-4,5-dihydrooxazole; With caesium carbonate; In toluene; at 110 ℃; for 72h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c8cc06649c

Reference yield:

2-bromobenzoic acid chloride (7154-66-7) + Phenylglycinol (20989-17-7,56613-80-0,71006-16-1,7568-92-5,188586-38-1) → 2-[2'-(diphenylphosphanyl)phenyl]-4-phenyl-4,5-dihydrooxazole (189169-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 24 h / 0 - 20 °C

1.2: 23 h / 0 - 20 °C

2.1: N,N`-dimethylethylenediamine; copper(l) iodide / toluene / 0.33 h / 20 °C / Schlenk technique; Inert atmosphere

2.2: 72 h / 110 °C / Schlenk technique; Inert atmosphere

With copper(l) iodide; triethylamine; N,N`-dimethylethylenediamine; In dichloromethane; toluene;

DOI:10.1039/c8cc06649c

Reference yield: 66.7%

tris(dibenzylideneacetone)dipalladium chloroform complex + 2-[2'-(diphenylphosphanyl)phenyl]-4-phenyl-4,5-dihydrooxazole (189169-55-9) + 1,2-Dicyanoethylene (764-42-1) → (+/-)-[2-[2'-(diphenylphosphanyl-κP)phenyl]-4,5-dihydro-4-phenyloxazole-κN](η(2)-fumarodinitrile)palladium(0)

Guidance literature:

In dichloromethane; under N2, Pd-complex, 2 equiv. of oxazoline-compd. were stirred for 30 min, 2 equiv. of nitrile was added, stirring at 20 °C for 2 h; soln. was concd., chromd. (SiO2, hexane/EtOAc=2:1), solvent was evapd., diastereomer ratio was 80:20;

DOI:10.1002/1099-0682(200206)2002:6<1511::aid-ejic1511>3.3.co;2-3

upstream raw materials:

2-(2-bromophenyl)-4-phenyl-4,5-dihydrooxazole

diphenylphosphane

2-bromobenzoic acid chloride

Phenylglycinol