493937
3-Methoxyindol
96%
Synonym(e):
3-Methyl-2-oxindol
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Alle Fotos(1)
About This Item
Empirische Formel (Hill-System):
C9H9NO
CAS-Nummer:
Molekulargewicht:
147.17
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22
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Assay
96%
Form
solid
mp (Schmelzpunkt)
117-121 °C (lit.)
SMILES String
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)
InChIKey
BBZCPUCZKLTAJQ-UHFFFAOYSA-N
Verwandte Kategorien
Allgemeine Beschreibung
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.
Anwendung
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
Lagerklassenschlüssel
11 - Combustible Solids
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
Persönliche Schutzausrüstung
Eyeshields, Gloves, type N95 (US)
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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)
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
J Thornton-Manning et al.
The Journal of pharmacology and experimental therapeutics, 276(1), 21-29 (1996-01-01)
The toxicity of 3-methylindole (3 MI), a selective pneumotoxin, is dependent upon cytochrome P450-mediated bioactivation 3. Using vaccinia-expressed P450 enzymes, the metabolites of radiolabeled 3 MI produced by 14 individual P450s were identified and quantified by high performance liquid chromatography.
Jaroslav Matal et al.
Neuro endocrinology letters, 30 Suppl 1, 36-40 (2009-12-23)
To study the contribution of individual purified porcine CYP1A2, 2E1 and 2A19 enzymes to the biotransformation of skatole. Individual porcine and human enzymes (CYP1A2, 2E1 or 2A6/19) were used to study their potential involvement in skatole metabolism. Furthermore, the inhibition
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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