Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate

Base Information

• Chemical Name: Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate
• CAS No.: 680971-62-4
• Molecular Formula: C15H11NO4
• Molecular Weight: 269.257
• DSSTox Substance ID: DTXSID00593907
• Nikkaji Number: J2.096.464B
• Wikidata: Q82488544
• Mol file: 680971-62-4.mol

Synonyms:680971-62-4;Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate;SCHEMBL5337208;DTXSID00593907;NCEPDURXEPWWKX-UHFFFAOYSA-N;phenyl 2,3-dihydro-4h-1,4-benzoxazin-3-one-4-carboxylate

Chemical Property of Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 269.06880783
• Heavy Atom Count: 20
• Complexity: 378

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)N(C2=CC=CC=C2O1)C(=O)OC3=CC=CC=C3

Technology Process of Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate

There total 1 articles about Phenyl 3-oxo-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate 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%

3,4-dihydro-3-oxo-2H-1,4-benzoxazine (5466-88-6) + phenyl chloroformate (1885-14-9) → phenyl 2,3-dihydro-4H-1,4-benzoxazin-3-one-4-carboxylate (680971-62-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2004.08.162

Reference yield: 92.0%

chlorophosphoric acid diphenyl ester (2524-64-3) + phenyl 2,3-dihydro-4H-1,4-benzoxazin-3-one-4-carboxylate (680971-62-4) → phenyl 3-[(diphenoxyphosphoryl)oxy]-4H-1,4-benzoxazine-4-carboxylate (680971-61-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.tetlet.2004.08.162

Reference yield:

phenyl 2,3-dihydro-4H-1,4-benzoxazin-3-one-4-carboxylate (680971-62-4) → 3-vinyl-benzo[1,4]oxazine-4-carboxylic acid phenyl ester (680971-67-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LDA / tetrahydrofuran / -78 °C

2: 83 percent / lithium chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 2 h / Heating

With lithium chloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 2: Stille coupling;

DOI:10.1016/j.tetlet.2004.08.162

upstream raw materials:

3,4-dihydro-3-oxo-2H-1,4-benzoxazine

phenyl chloroformate

Downstream raw materials:

phenyl 3-[(diphenoxyphosphoryl)oxy]-4H-1,4-benzoxazine-4-carboxylate

3-vinyl-benzo[1,4]oxazine-4-carboxylic acid phenyl ester

3-benzofuran-2-yl-benzo[1,4]oxazine-4-carboxylic acid phenyl ester