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395307

吲哚-3-甲酸甲酯

Name: 吲哚-3-甲酸甲酯
Brand: ALDRICH

99%

别名:

3-Carbomethoxyindole, 3-Methoxycarbonylindole, Methyl indolyl-3-carboxylate

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关于此项目

经验公式（希尔记法）:

C₁₀H₉NO₂

化学文摘社编号:

942-24-5

分子量:

175.18

NACRES:

NA.22

PubChem Substance ID:

24864651

UNSPSC Code:

12352100

MDL number:

MFCD00189407

Assay:

99%

Form:

powder

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属性

assay

99%

form

powder

mp

149-152 °C (lit.)

functional group

ester

SMILES string

COC(=O)c1c[nH]c2ccccc12

InChI

1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3

InChI key

QXAUTQFAWKKNLM-UHFFFAOYSA-N

说明

General description

Methyl indole-3-carboxylate (3-Methoxycarbonylindole, 3-Carbomethoxyindole, Methyl indolyl-3-carboxylate) has been extracted from the marine Streptomyces sp. 060524. Its crystal structure indicates the presence of intermolecular N-H…O hydrogen bond. It is also obtained during the isolation of sorazinones A and B from Sorangium cellulosum strain Soce895. It undergoes regioselective dibromination with bromine in acetic acid to afford methyl 5,6-dibromoindole-3-carboxylate.

Application

Reactant for preparation of:

Nitric oxide synthase (nNOS) inhibitorS
Protein kinase c alpha (PKCα) inhibitors
Inhibitors of the C-terminal domain of RNA polymerase II as antitumor agents
Kinase insert domain receptor (KDR) inhibitors
Organocatalysts for the anti-Mannich reaction
Very late antigen-4 (VLA-4) antagonists
Inhibitors of Human 5-Lipoxygenase
Serotonin 5-HT4 receptor antagonists
Hyaluronidase inhibitors

Reactant for:

Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions†

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Methyl indole-3-carboxylate.

Hu SC, et al.

Acta Crystallographica Section E, Structure Reports Online, 61(6), o1654-o1656 (2005)

Nannozinones and sorazinones, unprecedented pyrazinones from myxobacteria.

Rolf Jansen et al.

Journal of natural products, 77(11), 2545-2552 (2014-11-15)

Nannozinones A (1) and B (2) were discovered as metabolites of the recently isolated Nannocystis pusilla strain MNa10913 belonging to the poorly studied myxobacterial family Nannocystaceae. In contrast, the structurally related sorazinones A (5) and B (6) were isolated from

Regioselective dibromination of methyl indole-3-carboxylate and application in the synthesis of 5,6-dibromoindoles.

Thomas B Parsons et al.

Organic & biomolecular chemistry, 9(14), 5021-5023 (2011-06-07)

Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural

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全球贸易项目编号

货号	GTIN
395307-25G	04061831983043