1861-29-6

Basic information

• Product Name: 3-methyleneoxindole
• Synonyms: 3-methyleneoxindole;3-methyleneindolin-2-one;3-methylidene-1H-indol-2-one
• CAS NO: 1861-29-6
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• Mol File: 1861-29-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 353.7°C at 760 mmHg
• Flash Point: 204.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 3.53E-05mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 3-methyleneoxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyleneoxindole(1861-29-6)
• EPA Substance Registry System: 3-methyleneoxindole(1861-29-6)

Safety Data

• Hazardous Substances Data: 1861-29-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H7NO/c1-6-7-4-2-3-5-8(7)10-9(6)11/h2-5H,1H2,(H,10,11)

Upstream product

• 68543-20-4 3-acetoxy-3-methylindolin-2-one 
• 87-51-4 indole-3-acetic acid 
• 91-56-5 indole-2,3-dione 
• 19493-09-5 Methylenetriphenylphosphorane 
• 59-48-3 2-oxoindole 
• 50-00-0 formaldehyd 
• 16990-74-2 3-hydroxy-3-methyloxindole 
• 615-43-0 2-iodophenylamine 
• 154867-50-2 N-(2-iodophenyl)propiolamide 
• 292851-37-7 3-methoxycarbonyloxy-3-methylindolin-2-one 
• 292851-35-5 3-acetoxy-1-acetyl-3-methylindolin-2-one 

Downstream Products

• 18747-95-0 1-methyl-2-piperidinecarbonitrile 
• 1394133-24-4 3'-(4-(trifluoromethyl)phenyl)-4'H-spiro[indoline-3,5'-isoxazol]-2-one 
• 303740-09-2 3′-phenyl-4′H-spiro[indoline-3,5′-isoxazol]-2-one 
• 1394133-25-5 3'-(3-methoxyphenyl)-4'H-spiro[indoline-3,5'-isoxazol]-2-one 
• 303740-14-9 3'-(4-bromophenyl)-4'H-spiro[indoline-3,5'-isoxazol]-2-one 
• 1504-06-9 3-methylindolin-2-one 
• 1402725-16-9 ethyl 2'-benzyl-2-oxo-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-5'-carboxylate 
• 1402725-07-8 ethyl 2-oxo-2'-phenyl-2',4'-dihydrospiro[indoline-3,3'-pyrazole]-5'-carboxylate 
• 1402725-28-3 tert-butyl (2-(3-(benzylamino)-2-oxoindolin-3-yl)ethyl)carbamate 
• 1402725-26-1 2-(3-(benzylamino)-2-oxoindolin-3-yl)acetonitrile 
• 1402725-25-0 2-(2-oxo-3-(phenylamino)indolin-3-yl)acetonitrile 

Relevant articles and documents

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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.

Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides

Lewis acid-mediated conjugate addition of vinyl azides to electron-deficient alkenes led to the efficient construction of 1-pyrroline skeletons. The reactions of vinyl azides with 3-alkylidene-2-oxoindolines afford 3′,4′-dihydrospiro[indoline-3,2′-pyrrol]-2-ones in a diastereoselective fashion, whereas those with dimethyl 2-alkylidenemalonates provide 4,5-dihydro-3H-pyrroles.

Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors

The γ-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the d