3-Oxo-1-cyclopentanecarboxylic acid

Name: 3-Oxo-1-cyclopentanecarboxylic acid
Brand: ALDRICH
Price: 164 USD
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About This Item

Empirical Formula (Hill Notation):

C₆H₈O₃

CAS Number:

98-78-2

Molecular Weight:

128.13

NACRES:

NA.22

PubChem Substance ID:

24879119

UNSPSC Code:

12352100

MDL number:

MFCD01320173

Assay:

97%

Key Documents

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InChI

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

SMILES string

OC(=O)C1CCC(=O)C1

InChI key

RDSNBKRWKBMPOP-UHFFFAOYSA-N

assay

97%

mp

59-62 °C (lit.)

functional group

carboxylic acid, ketone

Quality Level

100

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Show Differences

1 of 4

This Item	553115	806455	555886
Sigma-Aldrich 550485 3-Oxo-1-cyclopentanecarboxylic acid	Sigma-Aldrich 553115 3-Methyl-4-pentenoic acid	Sigma-Aldrich 806455 2,6-Dimethoxyanilino(oxo)acetic acid	Sigma-Aldrich 555886 3-((tert-Butyldimethylsilyl)oxy)-propanol
assay 97%	assay 97%	assay -	assay 97%
Quality Level 100	Quality Level -	Quality Level 100	Quality Level 200
mp 59-62 °C (lit.)	mp -	mp -	mp -
functional group carboxylic acid	functional group carboxylic acid	functional group -	functional group hydroxyl

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.[1]

Application

3-Oxo-1-cyclopentanecarboxylic acid may be used in the preparation of 3-hydroxycyclopentanecarboxylic acid via hydrogenation.[2]

Substrate used in a study of biohydroxylation with mutants of cytochrome P450 BM-3.[3]

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

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)

Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3.

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

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Phase I Drug Metabolism

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

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3-Oxo-1-cyclopentanecarboxylic acid