(4S)-4-Phenyl-3-(1,2-propadienyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S)-4-Phenyl-3-(1,2-propadienyl)-2-oxazolidinone
• CAS No.: 845885-63-4
• Molecular Formula: C12H11 N O2
• Molecular Weight: 201.225
• DSSTox Substance ID: DTXSID70703879
• Nikkaji Number: J2.756.036I
• Mol file: 845885-63-4.mol

Synonyms:845885-63-4;(4S)-4-PHENYL-3-(1,2-PROPADIENYL)-2-OXAZOLIDINONE;(S)-4-phenyl-3-(propa-1,2-dien-1-yl)oxazolidin-2-one;DTXSID70703879;4beta-Phenyl-3-propadienyloxazolidine-2-one;(4S)-4-Phenyl-3-propadienyl-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-Phenyl-3-(1,2-propadienyl)-2-oxazolidinone

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 309.458°C at 760 mmHg
• Flash Point: 140.956°C
• PSA: 29.54000
• Density: 1.201g/cm³
• LogP: 2.41640
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=CN1C(COC1=O)C2=CC=CC=C2
• Isomeric SMILES: C=C=CN1[C@H](COC1=O)C2=CC=CC=C2

Technology Process of (4S)-4-Phenyl-3-(1,2-propadienyl)-2-oxazolidinone

There total 3 articles about (4S)-4-Phenyl-3-(1,2-propadienyl)-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%

(4S)-4-phenyl-3-(2-propynyl)oxazolidin-2-one (471247-94-6) → (4S)-4-phenyl-3-(1,2-propadienyl)-2-oxazolidinone (845885-63-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acscatal.0c02569

Reference yield: 82.0%

(S)-3-ethynyl-4-phenyloxazolidin-2-one + diazomethyl-trimethyl-silane (18107-18-1) → (4S)-4-phenyl-3-(1,2-propadienyl)-2-oxazolidinone (845885-63-4)

Guidance literature:

(S)-3-ethynyl-4-phenyloxazolidin-2-one; diazomethyl-trimethyl-silane; With copper(l) iodide; In diethyl ether; acetonitrile; at 25 ℃; for 3h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; acetonitrile; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.202103598

Reference yield:

4-phenyl-4-oxazoline-2-one (34375-80-9) → (4S)-4-phenyl-3-(1,2-propadienyl)-2-oxazolidinone (845885-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1: nickel diacetate; (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; hydrogen / 2,2,2-trifluoroethanol / 12 h / 50 °C / 760.05 Torr

2: sodium hydride / tetrahydrofuran / 20 °C

3: potassium tert-butylate / tetrahydrofuran / 20 °C

With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; potassium tert-butylate; hydrogen; nickel diacetate; sodium hydride; In tetrahydrofuran; 2,2,2-trifluoroethanol;

DOI:10.1021/acscatal.0c02569

upstream raw materials:

(4S)-4-phenyl-3-(2-propynyl)oxazolidin-2-one

4-phenyl-4-oxazoline-2-one

diazomethyl-trimethyl-silane