(E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one

Base Information

• Chemical Name: (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one
• CAS No.: 1619235-67-4
• Molecular Formula: C₂₇H₂₃NO₂
• Molecular Weight: 393.485

Synonyms:(E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one

Chemical Property of (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one

Chemical Property:

Purity/Quality:

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Technology Process of (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one

There total 7 articles about (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-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: 77.0%

4-Methoxystyrene (637-69-4,24936-44-5) + (E)-3-iodo-1-methyl-2-(2-phenyl)vinylquinolin-4(1H)-one (1619235-58-3) → (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one (1619235-67-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In acetonitrile; for 7h; Reagent/catalyst; Time; Reflux;

DOI:10.1016/j.tet.2014.05.040

Reference yield:

2-aminoacetophenone (551-93-9) → (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one (1619235-67-4)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexyl-carbodiimide; 4-pyrrolidin-1-ylpyridine / dichloromethane / 20 °C

2: sodium hydride / tetrahydrofuran

3: iodine; ammonium cerium (IV) nitrate / acetonitrile / 3 h / 80 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / acetonitrile / 7 h / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium (IV) nitrate; iodine; sodium hydride; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetonitrile; 4: |Heck Reaction;

DOI:10.1016/j.tet.2014.05.040

Reference yield:

(E)-3-phenylacrylic acid (140-10-3) → (E,E)-3-[2-(4-methoxyphenyl)vinyl]-1-methyl-2-(phenyl)vinylquinolin-4(1H)-one (1619235-67-4)

Guidance literature:

Multi-step reaction with 4 steps

1: dicyclohexyl-carbodiimide; 4-pyrrolidin-1-ylpyridine / dichloromethane / 20 °C

2: sodium hydride / tetrahydrofuran

3: iodine; ammonium cerium (IV) nitrate / acetonitrile / 3 h / 80 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / acetonitrile / 7 h / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium cerium (IV) nitrate; iodine; sodium hydride; 4-pyrrolidin-1-ylpyridine; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetonitrile; 4: |Heck Reaction;

DOI:10.1016/j.tet.2014.05.040

upstream raw materials:

2-aminoacetophenone

(E)-3-phenylacrylic acid

(2E)-N-(2-acetylphenyl)-3-phenylacrylamide

(E)-2-styrylquinolin-4(1H)-one

Downstream raw materials:

2-(4-methoxyphenyl)-10-methyl-3-phenylacridin-9(10H)-one

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