New Way for the Preparation of 4-Phenyl-2-oxobutyric Acid Ethyl Ester

Slavinska, V.; Sile, Dz.; Korchagova, E. Kh.; Katkevich, M. Yu.; Lukevics, É.

doi:10.1080/00397919608003583

Cited by 12 publications

(3 citation statements)

References 3 publications

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“…In the biochemical industry, it can be used as a synthetic precursor for n -butanol, l -alanine, l -tyrosine, isobutanol, and so on. In the pharmaceutical industry, it can be used to synthesize isoniazid pyruvate, vitamin B, and 4-phenyl-2-oxobutyric acid ethyl ester and has antioxidant effects . In the agricultural field, it can be used to synthesize pesticides such as cycloprothrin .…”

Section: Synthesis and Application Of Pyruvatementioning

confidence: 99%

Cell-Free Biosynthesis System: Methodology and Perspective of in Vitro Efficient Platform for Pyruvate Biosynthesis and Transformation

Tang

Liao

et al. 2021

ACS Synth. Biol.

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The modification of intracellular metabolic pathways by metabolic engineering has generated many engineered strains with relatively high yields of various target products in the past few decades. However, the unpredictable accumulation of toxic products, the cell membrane barrier, and competition between the carbon flux of cell growth and product synthesis have severely retarded progress toward the industrial-scale production of many essential chemicals. On the basis of an in-depth understanding of intracellular metabolic pathways, scientists intend to explore more sustainable methods and construct a cell-free biosynthesis system in vitro. In this review, the synthesis and application of pyruvate as a platform compound is used as an example to introduce cell-free biosynthesis systems. We systematically summarize a proposed methodology workflow of cell-free biosynthesis systems, including pathway design, enzyme mining, enzyme modification, multienzyme assembly, and pathway optimization. Some new methods, such as machine learning, are also mentioned in this review.

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Section: Synthesis and Application Of Pyruvatementioning

confidence: 99%

Cell-Free Biosynthesis System: Methodology and Perspective of in Vitro Efficient Platform for Pyruvate Biosynthesis and Transformation

Tang

Liao

et al. 2021

ACS Synth. Biol.

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“…The optimum conditions for the formation of ethyl 2-hydroxy-4-phenylbutyrate (yield 88.2%) were determined.Keywords: ethyl 4-substituted 2,4-dioxobutyrates, platinum and palladium catalysts, hydrogenation.The derivatives of 4-substituted 2-hydroxybutyric acids are valuable synthons for the production of antihypertensive substances, homoamino acids, hydroxamic acids, and other compounds [1,2].We studied the hydrogenation of sodium 2-oxo-4-phenyl-, 4-(2-furyl)-2-oxo-, 2-oxo-4-(2-thienyl)-, and 2-oxo-4-(3-pyridyl)butenoates at nickel and palladium catalysts.During the hydrogenation of sodium 2-oxo-4-phenylbutenoate at nickel catalysts the corresponding salt of 2-hydroxy-4-phenylbutyric acid is formed [3].The use of palladium black and 10% Pd/C catalyst leads to the formation of sodium 2-oxo-4phenylbutyrate. The former had low activity under the conditions we tested.…”

mentioning

confidence: 99%

“…During the hydrogenation of sodium 2-oxo-4-phenylbutenoate at nickel catalysts the corresponding salt of 2-hydroxy-4-phenylbutyric acid is formed [3].…”

mentioning

confidence: 99%

Hydrogenation of ethyl esters of 4-phenyl-and (2-furyl)-substituted 2,4-dioxobutyric acids at palladium black

Slavinska

Sile

Rozenthal

et al. 2006

Chem Heterocycl Compd

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The hydrogenation of ethyl 4- R-2,4-dioxobutyrates (R = phenyl, 2-furyl) at 5% Pt/Al 2 O 3 catalyst, modified with cinchonidine, and at palladium black was investigated. The former had low activity under the conditions we tested. The main products during the hydrogenation of these compounds at palladium black are ethyl 4-R-2-hydroxy-4-oxobutyrates. The yield of the phenyl derivative amounts to 68.5%, while the yield of the corresponding 2-furyl derivative amounts to 97%. In the last case ethyl 2-hydroxy-4-oxo-4-(2-tetrahydrofuryl)butyrate was detected as impurity. The optimum conditions for the formation of ethyl 2-hydroxy-4-phenylbutyrate (yield 88.2%) were determined.Keywords: ethyl 4-substituted 2,4-dioxobutyrates, platinum and palladium catalysts, hydrogenation.The derivatives of 4-substituted 2-hydroxybutyric acids are valuable synthons for the production of antihypertensive substances, homoamino acids, hydroxamic acids, and other compounds [1,2].We studied the hydrogenation of sodium 2-oxo-4-phenyl-, 4-(2-furyl)-2-oxo-, 2-oxo-4-(2-thienyl)-, and 2-oxo-4-(3-pyridyl)butenoates at nickel and palladium catalysts.During the hydrogenation of sodium 2-oxo-4-phenylbutenoate at nickel catalysts the corresponding salt of 2-hydroxy-4-phenylbutyric acid is formed [3].The use of palladium black and 10% Pd/C catalyst leads to the formation of sodium 2-oxo-4phenylbutyrate. During the hydrogenation of sodium 4-(2-furyl)-2-oxobutenoate at Raney nickel catalyst the corresponding 4-(2-furyl)-2-oxobutyrates and 4-(2-furyl)-2-hydroxybutyrates and aliphatic compounds from hydrogenolysis of the molecule of the original compound are formed [4].During the hydrogenation of sodium and ethyl 2-oxo-4-(2-thienyl)butenoates at Raney nickel the corresponding derivatives of 2-oxo-4-(2-thienyl)butyric acid and 2-hydroxy-4-(2-thienyl)butyric acid are formed [5]. Palladium catalysts secure the more selective formation of the corresponding oxo compound than Raney nickel. The formation of ethyl 2-oxo-4-(2-tetrahydrothienyl)butyrate in addition to the above-mentioned compounds was also observed during the hydrogenation of ethyl 2-oxo-4-(2-thienyl)butenoate at palladium black.During the hydrogenation of sodium 2-oxo-4-(3-pyridyl)butenoate at palladium black the reaction products were sodium 2-oxo-4-(3-pyridyl)butyrate and 2-hydroxy-4-(3-pyridyl)butyrate and hydrogenolysis products. The reaction takes place by a parallel-consecutive mechanism [6].During the hydrogenation of derivatives of 4-substituted 2-oxobutenoic acids the double bond is saturated, and the carbonyl group is partly hydrogenated. The latter depends on the composition of the catalyst and on the structure of the initial compound. __________________________________________________________________________________________

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ChemInform Abstract: New Way for the Preparation of 4‐Phenyl‐2‐oxobutyric Acid Ethyl Ester.

Slavinska¹,

Sile²,

Korchagova³

et al. 1996

ChemInform

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New Way for the Preparation of 4-Phenyl-2-oxobutyric Acid Ethyl Ester

Cited by 12 publications

References 3 publications

Cell-Free Biosynthesis System: Methodology and Perspective of in Vitro Efficient Platform for Pyruvate Biosynthesis and Transformation

Cell-Free Biosynthesis System: Methodology and Perspective of in Vitro Efficient Platform for Pyruvate Biosynthesis and Transformation

Hydrogenation of ethyl esters of 4-phenyl-and (2-furyl)-substituted 2,4-dioxobutyric acids at palladium black

ChemInform Abstract: New Way for the Preparation of 4‐Phenyl‐2‐oxobutyric Acid Ethyl Ester.

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