2-Oxazolidinone, 3-ethenyl-4-phenyl-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-ethenyl-4-phenyl-, (4S)-
• CAS No.: 128900-61-8
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Mol file: 128900-61-8.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 3-ethenyl-4-phenyl-, (4S)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Oxazolidinone, 3-ethenyl-4-phenyl-, (4S)-

There total 17 articles about 2-Oxazolidinone, 3-ethenyl-4-phenyl-, (4S)- 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: 95.0%

(R)-3-ethynyl-4-phenyl-1,3-oxazolidin-2-one (503590-46-3) → (4R)-4-phenyl-3-vinyl-oxazolidin-2-one (92288-03-4,128900-61-8,135741-19-4)

Guidance literature:

With hydrogen; Lindlar's catalyst; In dichloromethane; at 20 ℃; for 0.5h; under 760 Torr;

DOI:10.1021/jo060230h

Reference yield: 95.0%

Vinyl bromide (593-60-2,25951-54-6) + (4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) → (4R)-4-phenyl-3-vinyl-oxazolidin-2-one (92288-03-4,128900-61-8,135741-19-4)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 113 ℃; for 16h;

DOI:10.1021/jo702490w

Reference yield: 90.0%

bis(phenyl) carbonate (102-09-0) + Cr(CO)5C(CH3)NH(CH(C6H5)CH2OCOOC6H5) + sodium hydride (7646-69-7) → (4R)-4-phenyl-3-vinyl-oxazolidin-2-one (92288-03-4,128900-61-8,135741-19-4)

Guidance literature:

In tetrahydrofuran; byproducts: H2; Irradiation (UV/VIS); stirred at 25°C for 1h, stirring continued at 25°C for 3h, for a few hours to 2 days irradiated; NMR, IR, MS, elem. anal.;

DOI:10.1021/ja00173a012

upstream raw materials:

bis(phenyl) carbonate

(2S)-2-phenylglycinol

phenyl chloroformate

D-2-phenylglycinol

Downstream raw materials:

2-Methoxycarbonyl-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-pentanedioic acid dimethyl ester

(S)-3-((1S,4R)-3-Oxo-5-oxa-spiro[3.5]non-1-yl)-4-phenyl-oxazolidin-2-one

(S)-3-((1S,4R)-3-Oxo-5-oxa-spiro[3.4]oct-1-yl)-4-phenyl-oxazolidin-2-one

(S)-3-((1S,2R)-2-Cyclopropyl-2-methoxy-3-oxo-cyclobutyl)-4-phenyl-oxazolidin-2-one

Refernces

• 1、 Feltenberger, John B.,Hayashi, Ryuji,Tang, Yu,Babiash, Eric S.C.,Hsung, Richard P.. "Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions". supporting information; experimental part. p. 3666 - 3669. Retrieved 2011/02/25.
• 2、 Zhang, Xuejun,Zhang, Yanshi,Huang, Jian,Hsung, Richard P.,Kurtz, Kimberly C. M.,Oppenheimer, Jossian,Petersen, Matthew E.,Sagamanova, Irina K.,Shen, Lichun,Tracey, Michael R.. "Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocydic ynamides". . p. 4170 - 4177. Retrieved 2007/10/03.