(4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one
• CAS No.: 144838-82-4
• Molecular Formula: C18H17NO3
• Molecular Weight: 295.338
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50575450
• Nikkaji Number: J1.010.811J
• Wikidata: Q82464803
• Mol file: 144838-82-4.mol

Synonyms:144838-82-4;(R)-4-BENZYL-3-(2-PHENYLACETYL)OXAZOLIDIN-2-ONE;(4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one;(4R)-4-BENZYL-3-(2-PHENYLACETYL)-1,3-OXAZOLIDIN-2-ONE;SCHEMBL7346791;DTXSID50575450;AQFHLFHMTNGCPQ-MRXNPFEDSA-N;MFCD11036319;AKOS025402638;AS-35630;CS-0171289;A926648

Chemical Property of (4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one

Chemical Property:

• PSA: 46.61000
• LogP: 2.75710
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 295.12084340
• Heavy Atom Count: 22
• Complexity: 397

Purity/Quality:

97% ^*data from raw suppliers

(4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N(C(=O)O1)C(=O)CC2=CC=CC=C2)CC3=CC=CC=C3
• Isomeric SMILES: C1[C@H](N(C(=O)O1)C(=O)CC2=CC=CC=C2)CC3=CC=CC=C3
• Uses: (4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one is an intermediate in the synthesis of (+)-ar-Turmerone (T897275). (+)-ar-Turmerone is an anti-tumor and immune activating agent, which maintains a cytotoxic effect in cancer cells. Antimicrobial agent.

Technology Process of (4R)-4-Benzyl-3-(phenylacetyl)-1,3-oxazolidin-2-one

There total 6 articles about (4R)-4-Benzyl-3-(phenylacetyl)-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: 87.0%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + phenylacetyl chloride (103-80-0) → (4R)-4-Benzyl-3-(2-phenylacetyl)-1,3-oxazolan-2-one (144838-82-4)

Guidance literature:

(R)-4-(phenylmethyl)-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.166667h; Inert atmosphere;

phenylacetyl chloride; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 22.0833h; Inert atmosphere;

DOI:10.1016/j.tet.2011.07.065

Reference yield: 72.0%

phenylacetic acid (103-82-2) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (4R)-4-Benzyl-3-(2-phenylacetyl)-1,3-oxazolan-2-one (144838-82-4)

Guidance literature:

With pivaloyl chloride; triethylamine; In toluene; at 110 ℃; for 14h;

DOI:10.1016/S0040-4039(98)02112-1

Reference yield:

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + 2,2-dimethylpropanoicphenylacetic anhydride (864658-42-4) → (4R)-4-Benzyl-3-(2-phenylacetyl)-1,3-oxazolan-2-one (144838-82-4)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; hexane;

2,2-dimethylpropanoicphenylacetic anhydride; In tetrahydrofuran; diethyl ether; hexane; at -78 - 0 ℃; for 0.75h;

DOI:10.1055/s-2001-16757

upstream raw materials:

phenylacetic acid

(R)-4-(phenylmethyl)-2-oxazolidinone

phenylacetyl chloride

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

3-(4-tert-butylphenyl)-2-phenylpropan-1-ol

(2R)-1-[(4R)-4-Benzyl-2-oxo-1,3-oxazolan-3-yl]-3-(4-tert-butyldimethylsilyloxy-2,6-dimethylphenyl)-2-phenylpropan-1-one

(4R)-4-benzyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one

(+)-(R)-2-phenylpropanol