19155-24-9

Basic information

• Product Name: 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one
• Synonyms: 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one;3,3-DIMETHYLINDOLIN-2-ONE;1,2-Dihydro-3,3-dimethyl-2-oxo-3H-indole;3,3-DIMETHYL-1,3-DIHYDRO-INDOL-2-ONE;3,3-diMethyl-2,3-dihydro-1H-indol-2-one;2H-Indol-2-one, 1,3-dihydro-3,3-diMethyl-;2-Indolinone, 3,3-diMethyl-;Oxindole, 3,3-diMethyl-
• CAS NO: 19155-24-9
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• Mol File: 19155-24-9.mol
• Article Data: 59

Chemical Properties

• Melting Point: 154.3°C
• Boiling Point: 287.51°C (rough estimate)
• Flash Point: 172.6°C
• Appearance: /
• Density: 1.078
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.85±0.40(Predicted)
• CAS DataBase Reference: 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one(19155-24-9)
• EPA Substance Registry System: 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one(19155-24-9)

Safety Data

• Hazardous Substances Data: 19155-24-9(Hazardous Substances Data)

Usage

Description

1,3-Dihydro-3,3-dimethyl-2H-indol-2-one, also known as 3,3-Dimethyloxindole, is an organic compound with a unique chemical structure. It is characterized by its indole-based framework and two methyl groups attached to the 3rd carbon. 1,3-Dihydro-3,3-dimethyl-2H-indol-2-one has been identified for its potential applications in various fields due to its specific chemical properties and interactions.

Uses

Used in Pharmaceutical Industry:
1,3-Dihydro-3,3-dimethyl-2H-indol-2-one is used as an isoquinolin-1-amine based ROCK-I inhibitor for its ability to modulate specific cellular signaling pathways. This makes it a promising candidate for the development of novel therapeutics targeting various diseases and conditions.
Additionally, it is used in the preparation of P2Y1 antagonists, which are effacacious antiplatelet agents. These agents have potential applications in the treatment and prevention of thrombotic disorders, where they can help reduce the risk of blood clot formation and related complications.

Synthesis Reference(s)

Tetrahedron, 48, p. 7297, 1992 DOI: 10.1016/S0040-4020(01)88268-5

InChI:InChI=1/C10H11NO/c1-10(2)7-5-3-4-6-8(7)11-9(10)12/h3-6H,1-2H3,(H,11,12)

Upstream product

• 99984-56-2 3,3-dimethyl-3H-indole-2-carbonitrile 
• 112169-80-9 1-phenylcarbamoyl-3,3-dimethyloxindole 
• 72934-84-0 1-acetyl-3,3-dimethylindolin-2-one 
• 27333-47-7 1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b](1,4)-oxazine] 
• 64-17-5 ethanol 
• 5461-50-7 isobutyric acid-(N'-phenyl-hydrazide) 
• 20200-86-6 1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one 
• 25250-89-9 2H-indol-2-one 
• 74-88-4 methyl iodide 
• 201230-82-2 carbon monoxide 
• 52562-19-3 2-isopropenylaniline 
• 76-05-1 trifluoroacetic acid 
• 632324-67-5 tert-butyl 3,3-dimethyl-2-oxo-2,3-dihydroindole-1-carboxylate 
• 32353-29-0 1,3-dihydro-3,3-dimethyl-1-hydroxy-H-indol-2-one 

Downstream Products

• 185199-35-3 (S)-(+)-5-(2-chloro-1-oxo)propyl-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 
• 910562-97-9 benzyl 2,3,9,9a-tetrahydro-9,9-dimethyl-3-oxo-1H-imidazo[1,2-a]indole-3-carboxylate 
• 910562-96-8 benzyl [[(2-hydroxy-3,3-dimethyl-1-indolinyl)carbonyl]-methyl]carbamate 
• 101279-66-7 (3,3-dimethyl-indolin-2-ylidene)-phenyl-amine 
• 121677-90-5 3-methyl-1,5-bis-(3-methyl-benzothiazol-2-yl)-pentamethinium ; toluene-4-sulfonate 
• 917898-58-9 3,3-dimethyl-1-(2-nitrophenyl)indoline 
• 31523-05-4 5-amino-3,3-dimethyl-2-indolinone 
• 128271-19-2 1-(4-Chloro-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one 
• 34058-62-3 3,3-dimethyl-1-phenylindolin-2-one 
• 80711-56-4 1,3-dihydro-3,3-dimethyl-5-hydroxy-2H-indol-2-one 

Relevant articles and documents

Quinazolinones. I. Synthesis of indolo[2,1-b]quinazolinones

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Dirhodium(ii) tetraacetate catalysed reactions of diazo thioamides: Isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomuenchnones), an approach to analogues of dehydrogliotoxin

Dirhodium(II) tetraacetate catalysed reaction of the indoline diazo thioamide 8 gives the thioisomuenchnone 9, a stable characterisable solid. This masked thiocarbonyl ylide undergoes 1, 3-dipolar cycloaddition with N-methylmaleimide and maleic anhydride to give the exo-cycloadducts 10 and 11, characterised by X-ray crystallography. The thioisomuenchnone 18, derived from diazo thioamide 17, is an extremely stable crystalline mesoionic system which can be characterised by X-ray crystallography but fails to undergo intramolecular cycloaddition. The related thioisomnchnone 19 can be generated by reaction of indoline-2-thione 7 with bromoacetyl chloride in the presence of triethylamine, and undergoes cycloaddition, to give adducts 20 and 21.

Preparation of Complexes Bearing N-Alkylated, Anionic or Protic CAACs Through Oxidative Addition of 2-Halogenoindole Derivatives

CAAC precursors 2-chloro-3,3-dimethylindole 1 and 2-chloro-1-ethyl-3,3-dimethylindolium tetrafluoroborate 2BF4 have been prepared and oxidatively added to [M(PPh3)4] (M=Pd, Pt). Salt 2BF4 reacts with [Pd(PPh3)4] in toluene at 25 °C over 4 days to yield complex cis-[3]BF4 featuring an N-ethyl substituted CAAC, two cis-arranged phosphines and a chloro ligand. Compound trans-[3]BF4 was obtained from the same reaction at 80 °C over 1 day. Salt 2BF4 reacts with [Pt(PPh3)4] to give cis-[4]BF4. The neutral indole derivative 1 adds oxidatively to [Pt(PPh3)4] to give trans-[5] featuring a CAAC ligand with an unsubstituted ring-nitrogen atom. This nitrogen atom has been protonated with py?HBF4 to give trans-[6]BF4 bearing a protic CAAC ligand. The PdII complex trans-[7]BF4 bearing a protic CAAC ligand was obtained in a one-pot reaction from 1 and [Pd(PPh3)4] in the presence of py?HBF4.

NOVEL COMPOUNDS USEFUL AS POLY(ADP-RIBOSE) POLYMERASE (PARP) INHIBITORS

The present invention provides novel poly(ADP-ribose) polymerase (PARP) inhibitors, methods of preparing them, pharmaceutical compositions containing them and methods for the treatment, prevention and/or amelioration of PARP mediated diseases or disorders using them. In particular, the compounds described herein are useful for the treatment of carcinoma of the breast, ovarian cancer, carcinoma of the liver, carcinoma of the lung, small cell lung cancer, esophageal cancer, gall bladder cancer, pancreatic cancer and stomach cancer.

NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds

A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).