4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid

Base Information

• Chemical Name: 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid
• CAS No.: 1297310-88-3
• Molecular Formula: C₂₃H₁₆FNO₇
• Molecular Weight: 437.381
• Mol file: 1297310-88-3.mol

Synonyms:4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid

Chemical Property of 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid

There total 3 articles about 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid 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: 70.0%

4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester (1297310-86-1) → 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid (1297310-88-3)

Guidance literature:

4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester; With methanol; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=2; Cooling with ice;

DOI:10.1016/j.ejmech.2011.02.028

Reference yield:

3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone (1187551-48-9) → 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid (1297310-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 48 h / 80 °C / Inert atmosphere

2.1: sodium ethanolate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: methanol; sodium hydroxide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.2: pH 2 / Cooling with ice

With methanol; sodium ethanolate; palladium diacetate; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Heck reaction;

DOI:10.1016/j.ejmech.2011.02.028

Reference yield:

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate (1297310-96-3) → 4-[6-((E)-3-hydroxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid (1297310-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium ethanolate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

1.2: 0.5 h

2.1: methanol; sodium hydroxide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.2: pH 2 / Cooling with ice

With methanol; sodium ethanolate; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2011.02.028

upstream raw materials:

3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate

4-[6-((E)-3-ethoxy-3-oxoprop-1-enyl)-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-3-yl]-2-hydroxy-4-oxo-2-butenoic acid ethyl ester