2985-33-3

Usage

Uses

Ethyl 2-Carboxypropionate is a useful synthetic compound.

InChI:InChI=1/C6H10O4/c1-3-10-6(9)4(2)5(7)8/h4H,3H2,1-2H3,(H,7,8)

Upstream product

• 105-37-3 Ethyl propionate 
• 141-52-6 sodium ethanolate 
• 609-08-5 Diethyl methylmalonate 
• 541-41-3 chloroformic acid ethyl ester 
• 802294-64-0 propionic acid 
• 103362-70-5 potassium ethyl methylmalonate 
• 64-17-5 ethanol 
• 105-53-3 diethyl malonate 
• 1447797-55-8 diethyl 2-(3,5-di-tert-butylbenzyl)-2-methylmalonate 
• 1447797-53-6 diethyl 2-methyl-2-(4-(trifluoromethyl)benzyl)malonate 
• 2009-97-4 ethyl 2-diazo-3-oxobutanoate 
• 292638-85-8 acrylic acid methyl ester 
• 34780-08-0 2-(phenylthio)cyclopent-2-en-1-one 
• 50405-41-9 ethyl hydrogen methylmalonate magnesium enolate 

Downstream Products

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 608-40-2 meso 2,3-dimethylsuccinic acid 
• 608-40-2 rac-2,3-dimethylsuccinic acid 
• 97-63-2 methyl methacrylate 
• 371-26-6 ethyl 4,4,4-trifluorobutanoate 
• 56354-75-7 Ethyl 2-methyl-3,3,3-trifluoropropionate 
• 56354-77-9 2-Methyl-3-(2,2,2-trifluoro-ethyl)-succinic acid diethyl ester 
• 81997-76-4 (S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester 
• 81997-75-3 (S,Z)-ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylacrylate 
• 56834-42-5 2-methylmalonic acid tert-butyl ester ethyl ester 
• 1027196-76-4 C₂₃H₄₂N₄O₇ 
• 102-53-4 bis-(diethylamino)methane 
• 62116-13-6 2,2-dinitro-propionic acid ethyl ester 
• 105-37-3 Ethyl propionate 

Relevant academic research and scientific papers

Aspidosperma Alkaloids via Cyclization of Secodine Intermediate: Synthesis of (+/-)-3-Oxovincadifformine Ethyl Ester

(+/-)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular cycloaddition of the 3-oxosecodine 13 first prepared in turn from the enamide 10 by dehydrogenation with benzeneseleninic anhydride.An insight into the conversion of 10 into 13 was gained, resulting in the suggestion of a plausible mechanistic pathway.

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Hydrogen-Bonding Assisted Catalytic Kinetic Resolution of Acyclic β-Hydroxy Amides

Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.

4-Hydroxy-3-methyl-2(1h)-quinolone, originally discovered from a brassicaceae plant, produced by a soil bacterium of the genus burkholderia sp.: Determination of a preferred tautomer and antioxidant activity

4-Hydroxy-3-methyl-2(1H)-quinolone (1), a molecule known for a long time and recently discovered from a Brassicaceae plant Isatis tinctoria without providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related compounds and a synthetic preparation of 1, allowed its first full NMR characterization and identification of 2-quinolone but not 2-quinolinol (2) as the preferred tautomer for this heterocyclic system. While the metal-chelating activity was negligible, compound 1 at 10 μM, a concentration lower than that in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86percent. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response in the host organisms.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective.

Synthesis of α,β-Disubstituted Acrylates via Galat Reaction

Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.

Palladium-Catalyzed [3 + 2]-C-C/N-C Bond-Forming Annulation

The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji-Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. When the newly formed annulation product carries a properly located o-haloaryl moiety at the nitrogen substituent, a further intramolecular keto α-arylation can join the cascade, thereby forming two new cycles and three new bonds in the same synthetic operation.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

[7,6]-FUSED BICYCLIC ANTIDIABETIC COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.