3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-one

Base Information

• Chemical Name: 3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-one
• CAS No.: 90140-38-8
• Molecular Formula: C23H17NO2
• Molecular Weight: 339.393
• DSSTox Substance ID: DTXSID30365058
• Wikidata: Q82149427
• Mol file: 90140-38-8.mol

Synonyms:3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-one;90140-38-8;(4-hydroxy-6-methyl-2-phenyl-3-quinolinyl)(phenyl)methanone;3-Benzoyl-6-methyl-2-phenylquinolin-4(1H)-one;AB-321/43115530;DTXSID30365058

Chemical Property of 3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-one

Chemical Property:

• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 339.125928785
• Heavy Atom Count: 26
• Complexity: 581

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC(=C(C2=O)C(=O)C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of 3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-one

There total 5 articles about 3-benzoyl-6-methyl-2-phenyl-1H-quinolin-4-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: 88.0%

carbon monoxide (201230-82-2) + C22H18INO → 3-benzoyl-6-methyl-2-phenylquinolin-4(1H)-one (90140-38-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos; In acetonitrile; at 100 ℃; for 72h; under 15201 Torr;

DOI:10.1021/acs.jmedchem.6b01135

Reference yield: 76.0%

4-<α-(4-Methylphenylimino)benzyl>-5-phenyl-2,3-furandion (90140-28-6) → 3-benzoyl-6-methyl-2-phenylquinolin-4(1H)-one (90140-38-8)

Guidance literature:

at 140 ℃;

Reference yield:

phenylacetylene (536-74-3) → 3-benzoyl-6-methyl-2-phenylquinolin-4(1H)-one (90140-38-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.17 h / 20 °C

1.3: 2 h / 20 °C

2.1: methanol / 120 °C / Sealed tube

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; caesium carbonate / acetonitrile / 72 h / 100 °C / 15201 Torr

With bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; triethylamine; XPhos; In tetrahydrofuran; methanol; acetonitrile; 1.1: |Sonogashira Cross-Coupling / 1.2: |Sonogashira Cross-Coupling / 1.3: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.6b01135

upstream raw materials:

4-<α-(4-Methylphenylimino)benzyl>-5-phenyl-2,3-furandion

benzoyl chloride

phenylacetylene

carbon monoxide