(S)-4-Benzyl-3-(but-2-enoyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-(but-2-enoyl)oxazolidin-2-one
• CAS No.: 90719-30-5
• Molecular Formula: C14H15NO3
• Molecular Weight: 245.278
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID40879994
• Nikkaji Number: J352.341A,J516.220C
• Wikidata: Q81986760
• Metabolomics Workbench ID: 144400
• Mol file: 90719-30-5.mol

Synonyms:4-BCOX;4-benzyl-3-crotonyl-2-oxazolidinone

Chemical Property of (S)-4-Benzyl-3-(but-2-enoyl)oxazolidin-2-one

Chemical Property:

• Melting Point: 84-88 °C(lit.)
• Boiling Point: 351 °C at 760 mmHg
• PKA: -1?+-.0.40(Predicted)
• Flash Point: 166.1 °C
• PSA: 46.61000
• Density: 1.205 g/cm³
• LogP: 1.29870
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥30mg/mL
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 345

Purity/Quality:

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

Locostatin ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC(=O)N1C(COC1=O)CC2=CC=CC=C2
• Isomeric SMILES: C/C=C/C(=O)N1[C@H](COC1=O)CC2=CC=CC=C2

Technology Process of (S)-4-Benzyl-3-(but-2-enoyl)oxazolidin-2-one

There total 3 articles about (S)-4-Benzyl-3-(but-2-enoyl)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: 97.0%

trans-crotonic anhydride (623-68-7) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone (90719-30-5)

Guidance literature:

With triethylamine; lithium chloride; In tetrahydrofuran; at -15 - 20 ℃; for 12h;

DOI:10.1021/ol0631197

Reference yield: 93.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone (90719-30-5)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

trans-chrotonyl chloride; In tetrahydrofuran; at -78 - 0 ℃; for 0.75h;

DOI:10.1021/acs.joc.7b02104

Reference yield: 88.57%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + crotonyl chloride (10487-71-5) → (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone (90719-30-5)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

crotonyl chloride; In tetrahydrofuran; at -78 - 0 ℃; for 0.75h; Inert atmosphere;

upstream raw materials:

trans-chrotonyl chloride

(S)-4-Benzyl-2-oxazolidinone

trans-crotonic anhydride

crotonyl chloride

Downstream raw materials:

3-ethyl-2,5-dimethylcyclohex-2-en-1-one

(4S)-3-(4-(1-cylopentenyl)-3-methyl-1-oxobutyl)-4-(phenylmethyl)-2-oxazolidinone

(S)-4-Benzyl-3-((1S,2S,3R,4R)-3-methyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-oxazolidin-2-one

(4S)-4-benzyl-3-(3-methylbicyclo[2.2.1]hept-5-ene-2-carbonyl)oxazolidin-2-one

Refernces

• 1、 Leng, Lingying,Fu, Yue,Liu, Peng,Ready, Joseph M.. "Regioselective, Photocatalytic α-Functionalization of Amines". supporting information. p. 11972 - 11977. Retrieved 2020/08/06.
• 2、 -. "THIOPHEN-2-CARBOXYLIC ACID DERIVATIVES USEFUL AS INHIBITORS OF FLAVIVIRIDAE VIRUSES". Page/Page column 31; 32. . Retrieved 2013/03/26.