Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

Base Information

• Chemical Name: Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate
• CAS No.: 1027407-75-5
• Molecular Formula: C₂₁H₁₉NO₅
• Molecular Weight: 365.386
• UNII: C6Y6VB7RMC
• Mol file: 1027407-75-5.mol

Synonyms:1027407-75-5;C6Y6VB7RMC;Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate;UNII-C6Y6VB7RMC;1H-Indole-6-carboxylic acid, 1-acetyl-3-(ethoxyphenylmethylene)-2,3-dihydro-2-oxo-, methyl ester, (3Z)-;methyl (3Z)-1-acetyl-3-[ethoxy(phenyl)methylidene]-2-oxoindole-6-carboxylate;Methyl (Z)-1-Acetyl-3-[ethoxy(phenyl)methylene]-2-oxoindoline-6-carboxylate;SCHEMBL17147666;AC2735;CS-0111572

Chemical Property of Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

Chemical Property:

• Boiling Point: 555.7±50.0 °C(Predicted)
• Density: 1.278±0.06 g/cm3(Predicted)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 365.12632271
• Heavy Atom Count: 27
• Complexity: 635

Purity/Quality:

99% ^*data from raw suppliers

Methyl1-acetyl-3-[ethoxy(phenyl)methylidene]-2-oxoindole-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=C1C2=C(C=C(C=C2)C(=O)OC)N(C1=O)C(=O)C)C3=CC=CC=C3
• Isomeric SMILES: CCO/C(=C\1/C2=C(C=C(C=C2)C(=O)OC)N(C1=O)C(=O)C)/C3=CC=CC=C3

Technology Process of Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

There total 6 articles about Methyl (Z)-1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate 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: 51.0%

acetic anhydride (108-24-7) + 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (14192-26-8) + triethoxymethylbenzene (1663-61-2) → (Z)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1027407-75-5)

Guidance literature:

acetic anhydride; 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester; at 130 ℃; for 8h;

triethoxymethylbenzene; at 50 - 120 ℃; for 6h;

Reference yield:

1-acetyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (676326-36-6) + triethoxymethylbenzene (1663-61-2) → (Z)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1027407-75-5)

Guidance literature:

With acetic anhydride; at 100 ℃;

DOI:10.1021/jm100812a

Reference yield:

4-methoxycarbonylmethyl-3-nitrobenzoic acid methyl ester (334952-07-7) → (Z)-1-acetyl-3-(ethoxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1027407-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; palladium 10% on activated carbon; hydrogen / 2.5 h / 20 °C / 2585.81 Torr

2: toluene / 110 °C

With palladium 10% on activated carbon; hydrogen; acetic acid; In toluene;

upstream raw materials:

1-acetyl-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester

triethoxymethylbenzene

4-methoxycarbonylmethyl-3-nitrobenzoic acid methyl ester

methyl 3-nitrobenzoate

Downstream raw materials:

nintedanib

BIBF 1202

Refernces

• 1、 Edupuganti, Ramakrishna,Taliaferro, Juliana M.,Wang, Qiantao,Xie, Xuemei,Cho, Eun Jeong,Vidhu, Fnu,Ren, Pengyu,Anslyn, Eric V.,Bartholomeusz, Chandra,Dalby, Kevin N.. "Discovery of a potent inhibitor of MELK that inhibits expression of the anti-apoptotic protein Mcl-1 and TNBC cell growth". . p. 2609 - 2616. Retrieved 2017/04/06.
• 2、 Roth, Gerald J.,Heckel, Armin,Brandl, Trixi,Grauert, Matthias,Hoerer, Stefan,Kley, Joerg T.,Schnapp, Gisela,Baum, Patrick,Mennerich, Detlev,Schnapp, Andreas,Park, John E.. "Design, synthesis, and evaluation of indolinones as inhibitors of the transforming growth factor β receptor i (TGFβRI)". scheme or table. p. 7287 - 7295. Retrieved 2011/02/23.