6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone

Base Information

• Chemical Name: 6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone
• CAS No.: 54903-21-8
• Molecular Formula: C16H11 N O3
• Molecular Weight: 265.268
• Nikkaji Number: J3.231.152K
• Wikidata: Q76387545
• ChEMBL ID: CHEMBL249551
• Mol file: 54903-21-8.mol

Synonyms:JPB 51;6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone;2(3H)-Benzoxazolone, 6-(1-oxo-3-phenyl-2-propenyl)-;54903-21-8;CHEMBL249551;6-Cinnamoylbenzoxazole-2(3H)-one;LS-42444

Chemical Property of 6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone

Chemical Property:

• Density: 1.309g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 265.07389321
• Heavy Atom Count: 20
• Complexity: 412

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)C2=CC3=C(C=C2)NC(=O)O3
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(=O)C2=CC3=C(C=C2)NC(=O)O3

Technology Process of 6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone

There total 3 articles about 6-(1-Oxo-3-phenyl-2-propenyl)-2(3H)-benzoxazolone 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: 85.0%

6-acetyl-3H-benzooxazol-2-one (54903-09-2) + benzaldehyde (100-52-7) → 6-cinnamoylbenzo[d]oxazol-2(3H)-one (54903-21-8)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 20 ℃; for 16h;

DOI:10.1016/j.ejmech.2014.10.053

Reference yield:

2-Benzoxazolinone (59-49-4) → 6-cinnamoylbenzo[d]oxazol-2(3H)-one (54903-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / N,N-dimethyl-formamide / 4 h / 80 °C

2: potassium hydroxide / ethanol; water / 16 h / 20 °C

With aluminum (III) chloride; potassium hydroxide; In ethanol; water; N,N-dimethyl-formamide; 1: |Friedel-Crafts Acylation;

DOI:10.1016/j.ejmech.2014.10.053

Reference yield:

2-amino-phenol (95-55-6) → 6-cinnamoylbenzo[d]oxazol-2(3H)-one (54903-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 4 h / 70 °C

2: aluminum (III) chloride / N,N-dimethyl-formamide / 2 h / 75 °C / Inert atmosphere

3: potassium hydroxide / ethanol; water / 4 h / 20 °C

With aluminum (III) chloride; potassium hydroxide; In ethanol; water; N,N-dimethyl-formamide; acetonitrile; 2: |Friedel-Crafts Acylation / 3: |Claisen-Schmidt Condensation;

DOI:10.1021/jacs.7b10783

upstream raw materials:

6-acetyl-3H-benzooxazol-2-one

benzaldehyde

2-Benzoxazolinone

2-amino-phenol

Downstream raw materials:

6-(3-phenyl-propionyl)-3H-benzooxazol-2-one

2,7-dioxo-5-phenylcyclopenta-2,3-dihydro<1,3>benzoxazole

2-oxo-5-phenylcyclopenta-2,3-dihydro<1,3>benzoxazole