1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester

Base Information

• Chemical Name: 1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester
• CAS No.: 13672-24-7
• Molecular Formula: C19H17NO3
• Molecular Weight: 307.349
• DSSTox Substance ID: DTXSID301142424
• Nikkaji Number: J1.792.780I,J3.001.732C
• Mol file: 13672-24-7.mol

Synonyms:NSC99692;SCHEMBL12930191;DTXSID301142424;1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester;ethyl (2E)-2-(1-benzyl-2-oxo-indolin-3-ylidene)acetate;Ethyl (1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate;[[(E)-1-Benzyl-2-oxo-2,3-dihydro-1H-indole]-3-ylidene]acetic acid ethyl ester;Ethyl (2E)-2-[1,2-dihydro-2-oxo-1-(phenylmethyl)-3H-indol-3-ylidene]acetate;13672-24-7

Chemical Property of 1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 307.12084340
• Heavy Atom Count: 23
• Complexity: 479

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C1C2=CC=CC=C2N(C1=O)CC3=CC=CC=C3
• Isomeric SMILES: CCOC(=O)/C=C/1\C2=CC=CC=C2N(C1=O)CC3=CC=CC=C3

Technology Process of 1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester

There total 12 articles about 1-Benzyl-2-oxoindoline-3-ylideneacetic acid ethyl ester 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: 95.0%

1-benzylisatin (1217-89-6) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate (13672-24-7)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1039/c5cc10299e

Reference yield: 80.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 1-benzylisatin (1217-89-6) → ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate (13672-24-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/ol202646w

Reference yield: 61.0%

Ethyl isocyanoacetate (2999-46-4) + 1-benzylisatin (1217-89-6) → ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate (13672-24-7)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; In toluene; at 110 ℃; for 6h; Sealed tube;

DOI:10.1021/acs.orglett.8b00217

upstream raw materials:

1-benzylisatin

ethyl (triphenylphosphoranylidene)acetate

indole-2,3-dione

benzyl bromide

Downstream raw materials:

ethyl 2-(1-benzyl-2-oxoindolin-3-yl)acetate

(2'S,3'R)-ethyl 1-benzyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate

(2'R,3'R)-ethyl 1-benzyl-2-oxospiro[indoline-3,2'-oxirane]-3'-carboxylate

ethyl 2-(1-benzyl-2-oxoindolin-3-yl)-2-phenylacetate