(S)-4-Benzyl-2-oxazolidinone

Base Information

• Chemical Name: (S)-4-Benzyl-2-oxazolidinone
• CAS No.: 90719-32-7
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID00352970
• Nikkaji Number: J612.324D
• Wikidata: Q72441661
• Mol file: 90719-32-7.mol

Synonyms:(S)-4-Benzyl-2-oxazolidinone;90719-32-7;(s)-4-benzyloxazolidin-2-one;(4S)-4-benzyl-1,3-oxazolidin-2-one;(s)-(-)-4-benzyl-2-oxazolidinone;2-Oxazolidinone, 4-(phenylmethyl)-, (4S)-;(s)-4-benzyl-oxazolidin-2-one;MFCD00064496;(s)-4-(phenylmethyl)-2-oxazolidinone;(s)-(+)-4-benzyl-2-oxazolidinone;4-Benzyl-1,3-oxazolidin-2-one #;(S)-4-benzyloxazolidinone;SCHEMBL4328;(4S)-4-(Phenylmethyl)-1,3-oxazolidin-2-one;(S)-4-benzyl oxazolidinone;4beta-Benzyloxazolidin-2-one;4(S)-benzyl-2-oxazolidinone;4-(S)-benzyloxazolidin-2-one;(4S)-4-benzyl-2-oxazolidinone;(4S)-4-benzyloxazolidin-2-one;4-(S)-benzyl-oxazolidin-2-one;DTXSID00352970;(S)-4-benzyl-oxazolidine-2-one;CHEBI:194622;(S)(-)4-benzyl-2-oxazolidinone;s-(+)-4-benzyl-2-oxazolidinone;(4S)-4-benzyl oxazolidine-2-one;(S)-4-benzyl-oxazolidine-2- one;4(S)-phenylmethyl-2-oxazolidinone;(4S)-4-benzyl 1,3-oxazolidinone;(S)(-)-4-benzyl-2-oxazolidinone;4(S)-(-)-benzyl-2-oxazolidinone;CS-D1593;(S)-4-phenylmethyl-2-oxazolidinone;(S)-(-)-4-Benzyl-2-oxazolidineone;AKOS015839020;(4S)-(-)-4-benzyl-2-oxazolidinone;(4S)4-benzyl-1,3-oxazolidin-2-one;(S)-4-Benzyl-2-oxazolidinone, 99%;AC-4357;PS-6113;(S)-4-Benzyl-1,3-Oxazolidine-2-One;AM20090806;B1754;EN300-80370;Q-102352;Z1222283104

Chemical Property of (S)-4-Benzyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 86-88 °C(lit.)
• Refractive Index: -14.5 ° (C=5, MeOH)
• Boiling Point: 398.8 °C at 760 mmHg
• PKA: 12.78±0.40(Predicted)
• Flash Point: 195 °C
• PSA: 38.33000
• Density: 1.176 g/cm³
• LogP: 1.66630
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-Benzyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)CC2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](NC(=O)O1)CC2=CC=CC=C2
• Uses: (S)-(-)-4-Benzyl-2-oxazolidinone is used in chiral auxiliary asymmetric alkylation. It has been used in the synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides. It was used for asymmetric synthesis of (3R)- and (3S)-piperazic acid. As an oxazolidinone, (S)-4-Benzyl-2-Oxazolidinone can be used in chiral auxiliary asymetric synthesis.

Technology Process of (S)-4-Benzyl-2-oxazolidinone

There total 270 articles about (S)-4-Benzyl-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: 98.0%

(S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'R,2'S,7a'R,11R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Guidance literature:

With sodium methylate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2015.08.013

Reference yield: 98.0%

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Guidance literature:

With methanol; C₁₇H₂₃BN₂O; at 25 ℃; for 1h; under 760.051 Torr; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201200304

Reference yield: 97.0%

(S)-4-benzyl-3-((1'S,2'S,3'R,7a'R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one + carbonic acid dimethyl ester (616-38-6) → methyl (1'S,2'S,7a'R,11R)-1'-methyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate + (S)-4-Benzyl-2-oxazolidinone (90719-32-7)

Guidance literature:

With sodium methylate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2015.08.013

upstream raw materials:

4-methoxy-1,3-oxazolidin-2-one

benzylmagnesium chloride

(S)-4-Benzyl-3-[(2S,3R,4R,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6,8-dimethoxy-2-(4-methoxy-benzyloxy)-4,10-dimethyl-11-triisopropylsilanyloxy-undecanoyl]-oxazolidin-2-one

2-benzylaziridine

Downstream raw materials:

(S)-4-benzyloxazolidin-2-one-3-carbonyl chloride

(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

(4R)-3-(5-bromovaleryl)-4-phenylmethyl-2-oxazolidinone

(S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one

Refernces

• 1、 Cheviet, Thomas,Peyrottes, Suzanne. "Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism". . p. 3107 - 3119. Retrieved 2021/02/05.
• 2、 Yang, Qihao,Peng, Huaitao,Zhang, Qiuju,Qian, Xu,Chen, Xu,Tang, Xuan,Dai, Sheng,Zhao, Jiajun,Jiang, Kun,Yang, Qiu,Sun, Jian,Zhang, Linjuan,Zhang, Nian,Gao, Honglin,Lu, Zhiyi,Chen, Liang. "Atomically Dispersed High-Density Al–N4 Sites in Porous Carbon for Efficient Photodriven CO2 Cycloaddition". . . Retrieved 2021/09/20.