(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone

Base Information

• Chemical Name: (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone
• CAS No.: 131685-53-5
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.267
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID40450141
• Nikkaji Number: J2.246.904E,J653.063J
• Wikidata: Q72442867
• Mol file: 131685-53-5.mol

Synonyms:131685-53-5;(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone;(R)-4-Benzyl-3-propionyl-2-oxazolidinone;(R)-4-BENZYL-3-PROPIONYLOXAZOLIDIN-2-ONE;(4R)-4-benzyl-3-propanoyl-1,3-oxazolidin-2-one;2-Oxazolidinone, 3-(1-oxopropyl)-4-(phenylmethyl)-, (4R)-;MFCD00269687;N-Propionyl-(4R)-Benzyl-2-Oxazolidinone;SCHEMBL237075;DTXSID40450141;WHOBYFHKONUTMW-LLVKDONJSA-N;AMY14626;(r)-N-propanoyl-4-benzyloxazolidinone;AKOS015842713;CS-W009489;R-4-Benzyl-3-propionyl-2-oxazolidinone;AC-23909;AS-17488;3-Propanoyl-4alpha-benzyloxazolidine-2-one;(4R)-3-propanoyl-4-benzyl-2-oxazolidinone;(R)-4-Benzyl-3-propionyl-oxazolidin-2-one;A2754;B2165;N-3-propionyl-(4R)-benzyl- 2-oxazolidinone;(R)-3-(1-oxopropyl)-4-benzyl-2-oxazolidinone;(3R)-3-Propanoyl-4alpha-benzyloxazolidine-2-one;(4R)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one;J-006036;(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone, 99%;(R)-3-(1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone;(4R)-3-PROPIONYL-4-(PHENYLMETHYL)-2-OXAZOLIDINONE

Chemical Property of (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 45 °C
• Refractive Index: -103 ° (C=1, EtOH)
• Boiling Point: 396.639 °C at 760 mmHg
• PKA: -2.35±0.40(Predicted)
• Flash Point: 193.681 °C
• PSA: 46.61000
• Density: 1.206 g/cm³
• LogP: 1.92440
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform, Ethanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)N1C(COC1=O)CC2=CC=CC=C2
• Isomeric SMILES: CCC(=O)N1[C@@H](COC1=O)CC2=CC=CC=C2
• Uses: (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE is a oxazolidinone derivative used in the preparation of anisomycin analogues as activators of the JNK/SAPK1 and p38/SAPK2 pathways. (R)-(?)-4-Benzyl-3-propionyl-2-oxazolidinone can be used as a building block for the preparation of methyl 3-[(S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxopropyl]benzoate by treating with strong base followed by the addition of methyl 3-bromomethyl benzoate.

Technology Process of (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone

There total 30 articles about (R)-(-)-4-Benzyl-3-propionyl-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: 95.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionic acid anhydride (123-62-6) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8)

Guidance literature:

With electrogenerated base from 2-pyrrolidone; tetraethylammonium perchlorate; In acetonitrile; at 20 ℃;

DOI:10.1021/jo010038+

Reference yield: 94.0%

1-(1H-imidazol-1-yl)propan-1-one (4122-52-5) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; chemoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201203976

Reference yield: 91.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + propionyl chloride (79-03-8) + Diethyl carbonate (105-58-8,76619-83-5) → (S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; Diethyl carbonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

propionyl chloride; In tetrahydrofuran; hexane; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03299

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

propionyl chloride

propionic acid

propionic acid anhydride

Downstream raw materials:

<3(2S,3R)4S>-3-<3-hydroxy-2-methyl-6-heptenoyl>-4-benzyl-2-oxazolidinone

(S)-4-Benzyl-3-((R)-2-methyl-hex-4-ynoyl)-oxazolidin-2-one

<3(2S,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone

<3(2R,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone

Refernces

• 1、 -. "SUBSTITUTED TETRAHYDROFURANS AS MODULATORS OF SODIUM CHANNELS". Paragraph 00987-00988. . Retrieved 2021/06/11.
• 2、 Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun. "A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction". supporting information. . Retrieved 2020/03/30.