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Merck

493937

Sigma-Aldrich

3-Methyl-2-oxindole

96%

Sinónimos:

3-Methyloxindole

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About This Item

Fórmula empírica (notación de Hill):
C9H9NO
Número de CAS:
Peso molecular:
147.17
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

96%

Formulario

solid

mp

117-121 °C (lit.)

cadena SMILES

CC1C(=O)Nc2ccccc12

InChI

1S/C9H9NO/c1-6-7-4-2-3-5-8(7)10-9(6)11/h2-6H,1H3,(H,10,11)

Clave InChI

BBZCPUCZKLTAJQ-UHFFFAOYSA-N

Descripción general

3-Methyl-2-oxindole (MOI) is a 3-substituted-2-oxindole. It is reported to be formed during the oxidation of indole-3-acetic acid in the presence of FeII under aerobic conditions. MOI undergoes asymmetric anti-Mannich-type reaction with N-tosyl aryl aldimines in the presence of alkaloid cinchona derivatives to form anti-3,3-disubsituted 2-oxindole derivatives. It also undergoes asymmetric hydroxyamination with nitrosoarenes to form N-nitroso aldol products.

Aplicación

3-Methyl-2-oxindole may be used in the preparation of 3-hydroxy-3-methyl-2-oxindole.
  • Reactant for enantioselective α-amination reactions
  • Reactant for aldol reaction with glyoxal derivatives
  • Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes
  • Reactant for O-acetylation reactions
  • Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes.
Shen K, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 123(20), 4780-4784 (2011)
Ying Jin et al.
Chirality, 26(12), 801-805 (2014-07-22)
A series of cinchona alkaloid derivatives were used to catalyze the asymmetric anti-Mannich-type reaction of 3-methyl-2-oxindole with N-tosyl aryl aldimines. The resulting anti-3,3-disubstituted 2-oxindole products were obtained in good yields (up to 92%) with high diastereo- and enantioselectivities (anti/syn up
Metabolism and pneumotoxicity of 3-methyloxindole, indole-3-carbinol, and 3-methylindole in goats.
M J Potchoiba et al.
American journal of veterinary research, 43(8), 1418-1423 (1982-08-01)
Zhengyin Yan et al.
Analytical chemistry, 80(16), 6410-6422 (2008-07-23)
Constant neutral loss (CNL) and precursor ion (PI) scan have been widely used for the in vitro screening of glutathione conjugates derived from reactive metabolites, but these two methods are only applicable to triple quadrupole or hybrid triple quadrupole mass
Takuma Sakurai et al.
Microorganisms, 7(9) (2019-09-14)
Recent studies have shown that metabolites produced by microbes can be considered as mediators of host-microbial interactions. In this study, we examined the production of tryptophan metabolites by Bifidobacterium strains found in the gastrointestinal tracts of humans and other animals.

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