(4R,5R)-4,5-Diphenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,5R)-4,5-Diphenyl-2-oxazolidinone
• CAS No.: 23204-71-9
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.274
• DSSTox Substance ID: DTXSID401290220
• Nikkaji Number: J411.755G
• Mol file: 23204-71-9.mol

Synonyms:DTXSID401290220;(4R,5R)-4,5-Diphenyl-2-oxazolidinone;23204-71-9

Chemical Property of (4R,5R)-4,5-Diphenyl-2-oxazolidinone

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 239.094628657
• Heavy Atom Count: 18
• Complexity: 293

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2C(OC(=O)N2)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]2[C@H](OC(=O)N2)C3=CC=CC=C3

Technology Process of (4R,5R)-4,5-Diphenyl-2-oxazolidinone

There total 36 articles about (4R,5R)-4,5-Diphenyl-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: 84.0%

(4R,5R)-2-Benzyloxy-4,5-diphenyl-4,5-dihydro-oxazole → (4R,5R)-trans-4,5-diphenyl-2-oxazolidinone (23204-71-9)

Guidance literature:

With silica gel;

DOI:10.1016/S0040-4039(00)60736-0

Reference yield: 73.0%

4-((rel-(4R,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl)sulfonyl)benzonitrile → rel-(4R,5R)-4,5-diphenyloxazolidin-2-one (19190-95-5,19202-66-5,23204-70-8,23204-71-9,86286-49-9,86286-50-2,92552-75-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-dodecylthiol; In N,N-dimethyl-formamide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00253

Reference yield: 43.0%

isocyanate de chlorosulfonyle (1189-71-5) + trans-Stilbene oxide (1439-07-2) → (4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one (19456-17-8,27797-53-1,28521-60-0,68114-27-2) + rel-(4R,5R)-4,5-diphenyloxazolidin-2-one (19190-95-5,19202-66-5,23204-70-8,23204-71-9,86286-49-9,86286-50-2,92552-75-5)

Guidance literature:

isocyanate de chlorosulfonyle; trans-Stilbene oxide; In dichloromethane; at 0 - 20 ℃; for 1h;

With water; In dichloromethane; for 0.5h;

DOI:10.3762/BJOC.16.148

upstream raw materials:

(1RS,2SR)-2-chloro-1,2-diphenyl-ethylamine; hydrochloride

sodium carbonate

isocyanate de chlorosulfonyle

trans-Stilbene oxide

Downstream raw materials:

3-amino-4r,5t-diphenyl-oxazolidin-2-one

3-nitroso-4r,5t-diphenyl-oxazolidin-2-one

(4S,5S)-4,5-diphenyl-2-oxazolidinone

(4R,5S)-4,5-diphenyl-1,3-oxazolidin-2-one