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

Base Information

• Chemical Name: (E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate
• CAS No.: 1297310-96-3
• Molecular Formula: C₂₃H₂₀FNO₄
• Molecular Weight: 393.415
• Mol file: 1297310-96-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate 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: 62.0%

3-acetyl-6-bromo-1-((4-fluorophenyl)methyl)-4(1H)-quinolinone (1187551-48-9) + ethyl acrylate (140-88-5,9003-32-1) → (E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate (1297310-96-3)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 80 ℃; for 48h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.02.028

Reference yield: 79.0%

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate (1297310-96-3) + oxalic acid diethyl ester (95-92-1) → 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)

Guidance literature:

(E)-ethyl [3-acetyl-1-(4-fluorophenyl)methyl-4(1H)-quinolinon-6-yl]acrylate; oxalic acid diethyl ester; With sodium ethanolate; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In water; for 0.5h;

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

ethyl acrylate

Downstream raw materials:

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

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