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

Base Information

• Chemical Name: (4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one
• CAS No.: 23204-70-8
• Molecular Formula: C15H13 N O2
• Molecular Weight: 239.274
• Hs Code.: 2934999090
• European Community (EC) Number: 623-654-4
• DSSTox Substance ID: DTXSID70431963
• Nikkaji Number: J411.758A
• Wikidata: Q76414627
• Mol file: 23204-70-8.mol

Synonyms:23204-70-8;(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone;(4S,5R)-cis-4,5-Diphenyloxazolidin-2-one;(4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one;(4S,5R)-4,5-diphenyloxazolidin-2-one;cis-4,5-Diphenyl-2-Oxazolidinone;19202-66-5;(4S,5R)-4,5-diphenyl-2-oxazolidinone;2-Oxazolidinone, 4,5-diphenyl-, (4S,5R)-;rel-(4R*,5S*)-4,5-Diphenyloxazolidine-2-one;2-Oxazolidinone, 4,5-diphenyl-, cis-;SCHEMBL1443275;DTXSID70431963;LTENIVFVXMCOQI-UONOGXRCSA-N;4,5-cis-Diphenyl-2-oxooxazolidine;YAA20470;MFCD00799526;4beta,5beta-Diphenyloxazolidin-2-one;AKOS016842848;AS-43482;(4S,5R)-4,5-diphenyl-oxazolidin-2-one;(4S,5R)-(')-cis-4,5-Diphenyl-2-oxazolidinone;A878305;J-015031;(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone, 98%

Chemical Property of (4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 227-232 °C(lit.)
• Refractive Index: 1.591
• Boiling Point: 466.6°Cat760mmHg
• PKA: 11.56±0.60(Predicted)
• Flash Point: 236°C
• PSA: 38.33000
• Density: 1.192g/cm³
• LogP: 3.53760
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly)
• 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:

97% ^*data from raw suppliers

(4S,5R)-(-)-cis-Diphenyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

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
• Uses: (4S,5R)-(-)-cis-Diphenyl-2-oxazolidinone is used as a catalyst in the enantioselective synthesis of chiral phthalides. Versatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions, Diels-Alder reactions, cyclopropanations, and allylations.

Technology Process of (4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one

There total 53 articles about (4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one 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: 94.0%

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) + Diethyl carbonate (105-58-8,76619-83-5) → (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one (23204-70-8)

Guidance literature:

With sodium ethanolate; In ethanol; toluene; at 90 - 110 ℃; for 7h; Heating / reflux;

Reference yield: 91.0%

(4S,5R)-3-((S)-2-Methyl-propane-2-sulfinyl)-4,5-diphenyl-oxazolidin-2-one (813459-77-7) → (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one (23204-70-8)

Guidance literature:

With ammonia; lithium; ferric nitrate; at -78 ℃; for 0.5h;

DOI:10.1021/jo048576k

Reference yield: 89.0%

carbon dioxide (124-38-9,18923-20-1) + (1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) → (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one (23204-70-8)

Guidance literature:

carbon dioxide; (1R,2S)-2-Amino-1,2-diphenylethanol; With N(Et)4⁽¹⁺⁾*(2-pyrrolidone-anion); In acetonitrile; at 20 ℃; for 1h;

With p-toluenesulfonyl chloride; In acetonitrile; at 20 ℃; Further stages.;

DOI:10.1021/jo0002386

upstream raw materials:

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

sodium carbonate

isocyanate de chlorosulfonyle

trans-Stilbene oxide

Downstream raw materials:

(4R,5R)-trans-4,5-diphenyl-2-oxazolidinone

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

(4S,5R)-3-acetyl-4,5-diphenyloxazolidin-2-one

(4S,5R)-3-((E)-2-methyl-pent-2-enoyl)-4,5-diphenyl-oxazolidin-2-one