3359-49-7

Basic information

• Product Name: 3-benzylideneindolin-2-one
• Synonyms: 3-benzylideneindolin-2-one;3-(benzylidene)oxindole;3-(phenylmethylidene)-1H-indol-2-one;(3E)-3-benzylidene-1H-indol-2-one
• CAS NO: 3359-49-7
• Molecular Formula: C₁₅H₁₁NO
• Molecular Weight: 221.25
• Mol File: 3359-49-7.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 438°Cat760mmHg
• Flash Point: 262.3°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 7.14E-08mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 3-benzylideneindolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzylideneindolin-2-one(3359-49-7)
• EPA Substance Registry System: 3-benzylideneindolin-2-one(3359-49-7)

Safety Data

• Hazardous Substances Data: 3359-49-7(Hazardous Substances Data)

Usage

General Description

3-benzylideneindolin-2-one, also known as isatin or 2,3-dioxindole, is a heterocyclic compound with a bicyclic structure. It is a yellow crystalline solid that is widely used as a precursor in the synthesis of various pharmaceuticals, agrochemicals, and dyes. Isatin has been found to exhibit a wide range of biological activities, including anticancer, anti-inflammatory, and antimicrobial properties. It is also known to inhibit the activity of monoamine oxidase, an enzyme involved in the metabolism of neurotransmitters, making it a potential candidate for the treatment of neurological and psychiatric disorders. Isatin is a versatile and important compound in organic synthesis and medicinal chemistry, and its potential applications continue to be explored in various research areas.

InChI:InChI=1/C15H11NO/c17-15-13(10-11-6-2-1-3-7-11)12-8-4-5-9-14(12)16-15/h1-10H,(H,16,17)

Upstream product

• 3342-78-7 2-(2-aminophenyl)acetic acid 
• 100-52-7 benzaldehyde 
• 59-48-3 2-oxoindole 
• 100-51-6 benzyl alcohol 
• 38168-18-2 spiro[[1,3]dithiolane-2,3'-indolin]-2'-one 
• 110-89-4 piperidine 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 698-16-8 benzohydroximoyl chloride 
• 91-56-5 indole-2,3-dione 
• 16721-45-2 triphenyl(phenylmethylene)phosphorane 
• 615-43-0 2-iodophenylamine 
• 102-92-1 Cinnamoyl chloride 
• 118670-85-2 (2E)-N-(2-iodophenyl)-3-phenylprop-2-enamide 
• 443-69-6 5-fluoro-1H-indole-2,3-dione 

Downstream Products

• 343830-62-6 1-benzyl-(Z)-3-(benzylidene)indolin-2-one 
• 59181-30-5 3-benzylidene-1H-pyrrolo[2,3-b]pyridin-2(3H)-one 
• 7511-08-2 3-benzyl-2-oxindole 
• 71056-40-1 C₁₇H₁₃NO₂ 
• 1286738-58-6 (2'R,3S,4'R,5'R)-methyl 2-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate 
• 1286738-49-5 (2'R,3S,4'R,5'R)-methyl 2-oxo-4'-phenyl-2'-(p-tolyl)spiro[indoline-3,3'-pyrrolidine]-5'-carboxylate 
• 1286738-47-3 (2'R,3S,4'R,5'R)-methyl 2'-(2-bromophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate 

Relevant articles and documents

Electrochemical Umpolung C-H Functionalization of Oxindoles

Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.

Oxidative electro-organic synthesis of dimeric hexahydropyrrolo-[2,3-: B] indole alkaloids involving PCET: Total synthesis of (±)-folicanthine

An efficient electrochemical oxidation strategy for the total synthesis of a dimeric hexahydropyrrolo[2,3-b]indole alkaloid, (±)-folicanthine (1b), has been envisioned. Control experiments suggest that a PCET pathway involving stepwise electron transfer f

Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones

A copper-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described. By usingde novodesign of P-stereogenic phosphines as ligands, spiro[pyrrolidin-3,3'-oxindole]s are generated in good to excellent yields with high asymmetric induction. A further reduced catalyst loading of 0.1 mol% is sufficient to achieve a satisfactory enantioselectivity of 90% ee. The DFT calculations suggest the second Michael addition of the 1,3-dipole to be the rate- andenantio-determining step. A key feature of this 1,3-dipolar cycloaddition is the wide substrate applicability, even with alkyl aldehyde-derived azomethine ylide; thus it has streamlined a highly enantioselective access to a new class of antiproliferative agents, MDM2-p53.