550485
3-Oxo-1-cyclopentanecarboxylic acid
97%
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About This Item
Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
Molecular Weight:
128.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
97%
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
Related Categories
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.
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)
Regulatory Information
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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)
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
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)
Articles
Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.
一期生物转化反应在药物上引入或暴露官能团，目的是增加化合物的极性。尽管一期药物代谢发生在大多数组织中，但代谢的主要和首过部位发生在肝循环期间。
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