YLF-466D

Base Information

• Chemical Name: YLF-466D
• CAS No.: 1273323-67-3
• Molecular Formula: C₂₉H₂₀ClNO₃
• Molecular Weight: 465.936
• Mol file: 1273323-67-3.mol

Synonyms:3-[[(3E)-3-[(4-chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoic acid

Chemical Property of YLF-466D

Chemical Property:

Purity/Quality:

>98% ^*data from raw suppliers

3-[[(3E)-3-[(4-Chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 3-[[(3E)-3-[(4-Chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoic Acid is an activator of AMP-activated protein kinase (AMPK), which is a enzyme involved in the regulation of cellular energy homeostasis.

Technology Process of YLF-466D

There total 10 articles about YLF-466D 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:

3-phenylpropynoic acid phenylamide (7342-02-1) → 3-[[(3E)-3-[(4-chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoic acid (1273323-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: cesium fluoride; triphenylphosphine / palladium diacetate / tetrahydrofuran / 3 h / 110 °C / Inert atmosphere

3.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 50 °C

3.2: pH 3 / Acidic conditions

With lithium hydroxide monohydrate; water; caesium carbonate; triphenylphosphine; cesium fluoride; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester (1273324-41-6) → 3-[[(3E)-3-[(4-chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoic acid (1273323-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: cesium fluoride; triphenylphosphine / palladium diacetate / tetrahydrofuran / 3 h / 110 °C / Inert atmosphere

2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 50 °C

2.2: pH 3 / Acidic conditions

With lithium hydroxide monohydrate; water; triphenylphosphine; cesium fluoride; palladium diacetate; In tetrahydrofuran;

Reference yield:

aniline (62-53-3) → 3-[[(3E)-3-[(4-chlorophenyl)phenylmethylene]-2,3-dihydro-2-oxo-1H-indol-1-yl]methyl]benzoic acid (1273323-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dicyclohexyl-carbodiimide / dichloromethane / 14 h / 0 - 20 °C

2.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

3.1: cesium fluoride; triphenylphosphine / palladium diacetate / tetrahydrofuran / 3 h / 110 °C / Inert atmosphere

4.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 50 °C

4.2: pH 3 / Acidic conditions

With lithium hydroxide monohydrate; water; caesium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; cesium fluoride; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

aniline

phenylpropyolic acid

3-phenylpropynoic acid phenylamide

3-{[phenyl-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester

Refernces

• 1、 Novikova, Daria S.,Grigoreva, Tatyana A.,Ivanov, Gleb S.,Melino, Gerry,Barlev, Nickolai A.,Tribulovich, Vyacheslav G.. "Activating Effect of 3-Benzylidene Oxindoles on AMPK: From Computer Simulation to High-Content Screening". . p. 2521 - 2529. Retrieved 2020/09/21.
• 2、 Yu, Li-Fang,Li, Yuan-Yuan,Su, Ming-Bo,Zhang, Mei,Zhang, Wei,Zhang, Li-Na,Pang, Tao,Zhang, Run-Tao,Liu, Bing,Li, Jing-Ya,Li, Jia,Nan, Fa-Jun. "Development of novel alkene oxindole derivatives as orally efficacious AMP-activated protein kinase activators". . p. 475 - 480. Retrieved 2013/07/25.