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550485

Sigma-Aldrich

3-Oxo-1-cyclopentanecarboxylic acid

97%

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About This Item

Fórmula empírica (notación de Hill):
C6H8O3
Número de CAS:
98-78-2
Peso molecular:
128.13
MDL number:
MFCD01320173
UNSPSC Code:
12352100
PubChem Substance ID:
24879119
NACRES:
NA.22

assay

97%

mp

59-62 °C (lit.)

functional group

carboxylic acid
ketone

SMILES string

OC(=O)C1CCC(=O)C1

InChI

1S/C6H8O3/c7-5-2-1-4(3-5)6(8)9/h4H,1-3H2,(H,8,9)

InChI key

RDSNBKRWKBMPOP-UHFFFAOYSA-N

Categorías relacionadas

General description

3-Oxo-1-cyclopentanecarboxylic acid , also known as 3-oxocyclopentanecarboxylic acid, is a keto acid derivative. It undergoes Curtius rearrangement with diphenyl phosphoryl azide and triethylamine in tert-butanol to form the corresponding boc-protected 1-(3-oxo)urea derivative.

Application

3-Oxo-1-cyclopentanecarboxylic acid may be used in the preparation of 3-hydroxycyclopentanecarboxylic acid via hydrogenation.
Substrate used in a study of biohydroxylation with mutants of cytochrome P450 BM-3.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCS7463
MKBQ4033V
MKBF5530V
MKBC5956
MKAA4080

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Visite la Librería de documentos

Studies of Configuration. V. The Preparation and Configuration of cis-3-Methoxycyclopentanecarboxylic Acid.
Noyce D and Fessenden J.
The Journal of Organic Chemistry, 24(5), 715-717 (1959)
Boc-protected 1-(3-oxocycloalkyl) ureas via a one-step Curtius rearrangement: mechanism and scope.
Sun X, et al.
Tetrahedron Letters, 55(4), 842-844 (2014)
Dieter F Münzer et al.
Chemical communications (Cambridge, England), (20), 2597-2599 (2005-05-19)
Substrate engineered, achiral carboxylic acid derivative was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation

Artículos

Phase I Drug Metabolism

Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.

Phase I Drug Metabolism

Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.

Phase I Drug Metabolism

Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.

Phase I Drug Metabolism

Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.

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