13865-19-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-oxobutanoate is used as a starting material for the synthesis of (-)-deoxoprosophylline, a piperidine alkaloid with therapeutic potential. This application highlights its importance in the development of new pharmaceutical compounds.
Used in Chemical Industry:
Methyl 4-oxobutanoate is used as an intermediate in the preparation of important industrial compounds such as gamma-butyrolactone, 1,4-butanediol, and glutamate. Its role in the synthesis of these compounds makes it a valuable component in the chemical industry.
Used in Research and Development:
Methyl 4-oxobutanoate is used as a model substrate for exploring the asymmetric Henry reaction. This application is crucial for advancing the understanding of asymmetric synthesis and the development of new, more efficient methods for producing enantiomerically pure compounds.

References

Gresham, William F, R. E. Brooks, and W. M. Bruner. "Preparation of methyl 4-oxobutyrate." US2549454. 1951. Murib, Jawad H, and W. D. Baugh. "Process for the preparation of methyl 4-oxobutyrate and its methanol addition products." US, US5072005. 1991. https://www.scbt.com/scbt/product/methyl-4-oxobutanoate-13865-19-5

InChI:InChI=1/C5H8O3/c1-8-5(7)3-2-4-6/h4H,2-3H2,1H3

Upstream product

• 152343-04-9 methyl 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionate 
• 7647-01-0 hydrogenchloride 
• 62435-72-7 2,5-dimethoxy-2,5-dihydro-furan-2-carboxylic acid methyl ester 
• 96-48-0 4-butanolide 
• 67-56-1 methanol 
• 51534-81-7 dimethyl 2-(2,2-dimethoxyethyl)-1,3-propanedioate 
• 201230-82-2 carbon monoxide 
• 292638-85-8 acrylic acid methyl ester 
• 107-02-8 acrolein 
• 108-48-5 2,6-dimethylpyridine 
• 1490-25-1 succinic acid monomethylester chloride 
• 106-65-0 Dimethyl succinate 
• 611-13-2 2-furoic acid methyl ester 
• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 

Downstream Products

• 105-21-5 4-propylbutanolide 
• 617-65-2 Glutamic acid 
• 112081-57-9 3-((2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 112081-60-4 3-((2S,3R,4S,5S)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 112081-59-1 3-((2S,3R,4S,5R)-3-Cyclohexyl-4-methyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 153393-25-0 methyl 1-benzyl-4-oxo-2-imidazolidinepropanoate 
• 101853-52-5 (S)-4-Hydroxy-hexanoic acid methyl ester 
• 112375-44-7 (Z)-methyl 6-methylhept-4-enoate 
• 112081-58-0 3-((2S,3R,4S,5R)-3-Isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 95691-14-8 4-(Benzhydryl-amino)-4-hydroxyphosphinoyl-butyric acid methyl ester 
• 120056-44-2 cis-(1R,3R)-(+)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 84129-60-2 trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 4837-57-4 methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 60702-96-7 trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 

Relevant academic research and scientific papers

Asymmetric one-pot synthesis of five- and six-membered lactones via dynamic covalent kinetic resolution: Exploring the regio- and stereoselectivities of lipase

Cascade lipase-catalyzed lactonization has been applied to dynamic hemithioacetal formation, leading to efficient five- and six-membered lactone synthesis as well as chiral discrimination. Solvent-dependent regioselectivity was observed for the selective formation of 1,3-oxathiolan-5-one and γ-butyrolactone derivatives.

Synthesis of substituted γ- and δ-lactams through Mannich-type reactions of solid-supported N-acyliminium ions

We report the results of our recent investigations into the reactivity of cyclic solid-supported N-acyliminium ions. An intermolecular Mannich-type transformation of these intermediates was used to generate libraries of substituted lactams. Masked aldehyde building blocks were readily prepared and coupled to peptides immobilized on PEGA800(polyethylene glycol dimethyl acrylamide) resin through an HMBA [4-(hydroxymethyl)benzoic acid] linker. When treated with acid, the aldehyde was cleanly released and condensed with the amide backbone to form a hydroxylactam/N-acyliminium ion, which underwent intermolecular reactions with a series of nucleophilic heterocycles, such as substituted indoles, thiophenes, furans, and electron-rich benzenes. The resulting lactams were formed within a few minutes and in high purities (typically >85 %). A new and efficient method for the solid-phase synthesis of diversely substituted γ- and δ-lactams through Mannich-type reactions of cyclic N-acyliminium ions is presented. A wide range of external aromatic and heteroaromatic carbon nucleophiles could be successfully used in the sequence.

A mild and efficient Nef reaction for the conversion of nitro to carbonyl group by dimethyldioxirane (DMD) oxidation of nitronate anions

DMD oxidation of nitronate onions, generated in situ from the corresponding nitroalkanes, affords the corresponding carbonyl products. Highest yields were obtained when one equivalent of water was added before the oxidation with DMD.

STEREOSPECIFIC CONSTRUCTION OF EXO-TETRASUBSTITUTED OLEFINS. THE EFFICIENT SYNTHESIS OF CYANO-CARBACYCLINS

Cyano-carbacyclins (2 and 3) were efficiently sythesized using the stereospecific 1,4-hydrogenation of the corresponding conjugated diene 10a catalyzed by the arene.Cr(CO)3 complex as a key step.

A new, highly selective, water-soluble rhodium catalyst for methyl acrylate hydroformylation

Hydroformylation of methylacrylate to α-aldehyde can be achieved in a two-phase system in the presence of two new water-soluble phosphines.High yields and selectivities of α-aldehyde (ca. 80percent with a α/β ratio of 1:20) were obtained.Spectroscopic studies have been carried out and some new rhodium complexes formed in situ in catalytic systems have been identified.Keywords: Hydroformylation; Methyl acrylate; Water-soluble phosphines; Rhodium; Catalysis; Two phase system

New Reagents for the Regiospecific Synthesis of Naturally Occurring Quinizarins

A modified Nef reaction applied to 4-nitrobutanoates gives the corresponding acetals which after hydrolysis and enol silylation yield the new 1,3-dienes 1-methoxy-1,4-bis(trimethylsiloxy)butadiene and its 3-methyl derivative.The latter reacts smoothly with chloronaphthoquinones and provides simple and efficient syntheses of 2-methylquinizarin, islandicin, digitopurpone, and erythroglaucin.

Synthesis of Optically Active Maresin 2 and Maresin 2 n-3 DPA

Maresins are among the most potent antiinflammatory lipid metabolites. We report stereoselective syntheses of maresin 2 and maresin 2 n-3 DPA. The anti -diol was constructed through epoxide ring opening of an optically active β,γ-epoxy aldehyde, synthesized in situ by Swern oxidation of the corresponding alcohol. Finally, the target compounds were synthesized through a Sonogashira coupling of a C9-C22 iodide and methyl (Z)-oct-4-en-7-ynoate or methyl oct-7-ynoate, respectively.

Total Synthesis of DHA and DPA n-3Non-Enzymatic Oxylipins

Oxylipins are formed in vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentane, tetrahydrofuran, hydroxylated-PUFA, etc.). All structures of oxylipins are of great biological interest. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies, and more especially, they were found to have their own biological properties. Produced in vivo as a non-separable mixture of isomers, their total synthesis is a keystone to answer biological questions. In this work, the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) is described using a unique and convergent synthetic strategy.

Catalyst composition containing bidentate phosphine ligand and application thereof

The catalyst composition comprises a bidentate phosphine ligand and a rhodium complex, wherein the skeleton of the bidentate phosphine ligand not only has C. 2 The symmetry and the appropriate rigidity, and the phosphine ligand derived based on the skeleton can provide effective steric hindrance around the catalyst center metal, so that the selectivity of the catalyst can be remarkably improved, the aldehyde yield is not lower 92% when the catalyst combination is applied to the hydroformylation reaction, and the selectivity of n-aldehyde is not lower 90%. In addition, the raw materials olefins with different structures can obtain outstanding reaction rate and normal aldehyde selectivity as compared with the existing catalyst systems, and can be suitable for the hydroformylation reaction of more types of olefins.

NEW COMPOUNDS FOR TREATMENT OF DISEASES RELATED TO DUX4 EXPRESSION

The present invention relates to compounds for the treatment of diseases related to DUX4 expression, such as muscular dystrophies. It also relates to use of such compounds, or to methods of use of such compounds.