90828-09-4

Basic information

• Product Name: 2H-Indol-2-one, 1,3-dihydro-3-[(4-methylphenyl)methylene]-, (E)-
• CAS NO: 90828-09-4
• Molecular Formula: C16H13NO
• Molecular Weight: 235.285
• Mol File: 90828-09-4.mol

Chemical Properties

• CAS DataBase Reference: 2H-Indol-2-one, 1,3-dihydro-3-[(4-methylphenyl)methylene]-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indol-2-one, 1,3-dihydro-3-[(4-methylphenyl)methylene]-, (E)-(90828-09-4)
• EPA Substance Registry System: 2H-Indol-2-one, 1,3-dihydro-3-[(4-methylphenyl)methylene]-, (E)-(90828-09-4)

Safety Data

• Hazardous Substances Data: 90828-09-4(Hazardous Substances Data)

Upstream product

• 59-48-3 2-oxoindole 
• 104-87-0 4-methyl-benzaldehyde 
• 201230-82-2 carbon monoxide 
• 124643-45-4 2-(p-tolylethynyl)aniline 
• 104-84-7 para-methylbenzylamine 

Downstream Products

• 90828-08-3 3‐(p‐tolylimino)indolin‐2‐one 
• 1262120-75-1 (Z)-2-(2-oxoindolin-3-ylidene)-2-(4-tolyl)acetonitrile 

Relevant articles and documents

Synthesis of (E)-3-Alkylideneindolin-2-ones by an Iron-Catalyzed Aerobic Oxidative Condensation of Csp3–H Bonds of Oxindoles and Benzylamines

A novel synthetic route for the construction of (E)-3-alkylideneindolin-2-ones through iron-catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self-condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3-alkylideneindolin-2-one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.

Selective C3-alkenylation of oxindole with aldehydes using heterogeneous CeO2 catalyst

We report herein that a commercially available CeO2 is an active and reusable catalyst for the C3-selective alkenylation of oxindole with aldehydes under solvent-free conditions. This catalytic method is generally applicable to different aromatic and aliphatic aldehydes, giving 3-alkyledene-oxindoles in high yields (87%–99%) and high stereoselectivities (79%–93% to E-isomers). This is the first example of the catalytic synthesis of 3-alkenyl-oxindoles from oxindole and various aliphatic aldehydes. The Lewis acid-base interaction between Lewis acid sites on CeO2 and benzaldehyde was studied by in situ IR. The structure-activity relationship study using CeO2 catalysts with different sizes suggests that defect-free CeO2 surface is the active site for this reaction.

Piers-rubinsztajn reaction and the application in siloxane/polysiloxane chemistry

An efficient synthesis of biologically important benzylidene-indolin-2-one derivatives using meglumine as green catalyst and ethanol:water as reaction media at 78°C has been developed. The effects of reaction conditions such as solvents, temperature, and amount of catalyst were investigated. The present methodology offers many advantages such as simple procedure, less time taking to complete the reaction, high yield of products, and clean reaction profile.

Solvent-free synthesis of novel spirocyclic oxindole derivatives via a Michael-aldol cascade by grinding

A simple and novel synthesis of spirocyclic oxindole derivatives by the reaction of (E)-3-arylideneindole-2-ones and 1,4-dithiane-2,5-diol via a Michael-aldol cascade under solvent-free reaction conditions is reported. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4′,5′-dihydro-2′H-spiro[oxindole-3,3′-thiophen]-2-ones in moderate to good yields. The structures of all the products were characterised by NMR, infrared spectroscopy and HRMS.

Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare

In our continued efforts to improve the potential utility of the α-methylene-γ-lactone scaffold, 62 new and 59 known natural α-methylenelactam analogues including α-methylene-γ-lactams, α-arylidene-γ and δ-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the α-methylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50?=?10.4?μM but less cytotoxic activity with IC50?=?141.2?μM (against HepG2 cell line) and 161.2?μM (against human hepatic L02?cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C.?orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structure–activity relationships revealed that incorporation of the aryl group into the α-exo-methylene and the N-benzyl substitution increased the activity. Meanwhile, the α-arylidene-γ-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N-benzyl substituted α-(2-fluorophenyl)-γ-lactam was identified as the most promising natural-based scaffold for further discovering and developing improved crop-protection agents.

3-substituted arylcarbonylindol-2-ketone and preparation method thereof

The invention relates to 3-substituted arylcarbonylindol-2-ketone and a preparation method thereof. According to the preparation method, indole-2-ketone and aromatic aldehyde are taken as raw materials, and a 3-substituted arylcarbonylindol-2-ketone compound with moderate-good yield is obtained through catalytic synthesis of inorganic salt under a mild condition. The preparation method has the characteristics of being quick in reaction speed, mild in reaction conditions, simple and convenient to operate and the like.

Investigation of triazole-linked indole and oxindole glycoconjugates as potential anticancer agents: Novel Akt/PKB signaling pathway inhibitors

In continuation of our venture towards the synthesis of novel bioactive agents, two sets of triazole-linked glycoconjugates were synthesized from indole/oxindole (29 compounds) and were further characterized by IR (infrared spectroscopy), 1H NM

Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity

Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventive potential. To investigate this possibility, we have synthesized and evaluated a series of functionalized 3-benzylidene-indolin-2-ones for induction of NQO1 in murine Hepa1c1c7 cells as well as antiproliferative activity against two human cancer cell lines (MCF-7, HCT116). The benzylideneindolinones were found to be good inducers of NQO1 activity, with 85% of test compounds able to increase basal NQO1 activity by more than twofold at concentrations of ≤10 μM. By contrast, fewer compounds (11%) tested at the same concentration were able to reduce cell viability by more than 50%. Structure activity relationships showed that the nitrogen linked Michael acceptor moiety was an essential requirement for both activities. This common feature notwithstanding, substitution of the 3-benzylidene-indolin-2-one core structure affected NQO1 induction and antiproliferative activities in dissimilar ways, underscoring different structural requirements for these two activities. Nonetheless, promising compounds (10, 42, 45-48) were identified that combine selective induction of NQO1 with potent antiproliferative activity. A potential advantage of such agents would be the ability to provide added protection to normal cells by the up-regulation of NQO1 and other phase II enzymes while simultaneously targeting neoplastic cells.

Heterobimetallic cobalt/rhodium nanoparticle-catalyzed carbonylative cycloaddition of 2-alkynylanilines to oxindoles

(Chemical Equation Presented) The cobalt-rhodium heterobimetallic nanoparticle-catalyzed synthesis of oxindoles from 2-alkynylanilines in the presence of carbon monoxide is described.

(Z)- AND (E)-ARYLIDENE-1,3-DIHYDROINDOL-2-ONES : CONFIGURATION, CONFORMATION, AND INFRARED CARBONYL STRETCHING FREQUENCIES

The configuration and conformation of both (Z)- and (E)-arylidene-1,3-dihydroindol-2-ones were investigated.In the solid state the Z-isomer is planar whereas the E-isomer has the aryl group significantly twisted, as shown by two X-ray structures.A linear