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375322

Sigma-Aldrich

2-Oxo-4-phenyl-buttersäure-ethylester

97%

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About This Item

Lineare Formel:
C6H5CH2CH2COCOOCH2CH3
CAS-Nummer:
64920-29-2
Molekulargewicht:
206.24
Beilstein:
2725083
EG-Nummer:
265-276-9
MDL-Nummer:
MFCD00037533
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24863381
NACRES:
NA.22

Assay

97%

Form

liquid

Brechungsindex

n20/D 1.504 (lit.)

bp

132 °C/2 mmHg (lit.)

Dichte

1.091 g/mL at 25 °C (lit.)

SMILES String

CCOC(=O)C(=O)CCc1ccccc1

InChI

1S/C12H14O3/c1-2-15-12(14)11(13)9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

InChIKey

STPXIOGYOLJXMZ-UHFFFAOYSA-N

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Allgemeine Beschreibung

Ethyl 2-oxo-4-phenylbutyrate is an aliphatic α-ketoester. Bioreduction of ethyl 2-oxo-4-phenylbutyrate is reported to yield ethyl (R)-2-hydroxy-4-phenylbutanoate. The effect of ionic liquid on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae has been reported. Asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate using a bacterial reductase is reported. Enantioselective hydrogenation of ethyl 2-oxo-4-phenylbutyrate using homogeneous Rh-diphosphine and heterogeneous Pt/Al2O3-cinchona catalysts has been reported.

Anwendung

Ethyl 2-oxo-4-phenylbutyrate may be used in the synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate, an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitor.

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 2

Flammpunkt (°F)

235.4 °F - closed cup

Flammpunkt (°C)

113 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Gloves

Analysenzertifikate (COA)

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Efficient Reduction of Ethyl 2-Oxo-4-phenylbutyrate at 620 g? L- 1 by a Bacterial Reductase with Broad Substrate Spectrum.
Ni Y, et al.
J. Mol. Catal. A: Chem., 107(1), 85-94 (1996)
Yu-Gang Shi et al.
Journal of industrial microbiology & biotechnology, 35(11), 1419-1424 (2008-08-22)
The effect of ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) on the asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate (EOPB) to synthesize optical active ethyl 2-hydroxy-4-phenylbutyrate (EHPB) catalyzed by Saccharomyces cerevisiae was investigated. (R)-EHPB [70.4%, e.e.(R)] is obtained using ethyl ether or benzene as
Efficient Reduction of Ethyl 2-Oxo-4-phenylbutyrate at 620 g? L- 1 by a Bacterial Reductase with Broad Substrate Spectrum.
Ni Y, et al.
Advanced Synthesis & Catalysis, 353(8), 1213-1217 (2011)
Nai-Dong Shen et al.
Organic letters, 14(8), 1982-1985 (2012-04-07)
A new reductase, CgKR2, with the ability to reduce ethyl 2-oxo-4-phenylbutyrate (OPBE) to ethyl (R)-2-hydroxy-4-phenylbutyrate ((R)-HPBE), an important chiral precursor for angiotensin-converting enzyme (ACE) inhibitors, was discovered. For the first time, (R)-HPBE with >99% ee was produced via bioreduction of
Ye Ni et al.
Journal of biotechnology, 168(4), 493-498 (2013-10-15)
Ethyl (R)-2-hydroxy-4-phenylbutanoate [(R)-HPBE] is a versatile and important chiral intermediate for the synthesis of angiotensin-converting enzyme (ACE) inhibitors. Recombinant E. coli strain coexpressing a novel NADPH-dependent carbonyl reductase gene iolS and glucose dehydrogenase gene gdh from Bacillus subtilis showed excellent

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