4075-58-5

Usage

Uses

Used in Drug Discovery:
ETHYL THIOPHENE-2-GLYOXYLATE is used as a compound for drug discovery, particularly through chemic informatics-based design. Its unique chemical structure allows for the development of potential therapeutic agents and contributes to the advancement of pharmaceutical research.
Used as a Catalyst:
In the chemical industry, ETHYL THIOPHENE-2-GLYOXYLATE serves as a catalyst, facilitating various chemical reactions and improving the efficiency of production processes. Its catalytic properties make it a valuable component in the synthesis of different compounds.
Used in Synthesis of Raw Material:
ETHYL THIOPHENE-2-GLYOXYLATE is also employed in the synthesis of raw materials, which are essential for the production of various products in the chemical and pharmaceutical industries. Its role in the synthesis process highlights its importance in the development of new materials and compounds with potential applications in multiple sectors.

Upstream product

• 188290-36-0 thiophene 
• 4755-77-5 Ethyl oxalyl chloride 
• 4075-59-6 2-thiopheneglyoxylic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 95-92-1 oxalic acid diethyl ester 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 64-17-5 ethanol 
• 872-55-9 2-ethylthiophene 
• 141-78-6 ethyl acetate 
• 33898-90-7 2-Thenoylacetonitrile 
• 57382-97-5 ethyl thiophen-2-ylacetate 
• 1003-09-4 2-bromothiophene 
• 82219-12-3 ethyl 2-(thiophen-2-yl)acetimidate hydrochloride 

Downstream Products

• 28569-78-0 hydroxy-phenyl-[2]thienyl-acetic acid ethyl ester 
• 28569-88-2 Ethyl (2,2'-Dithienyl)glycolate 
• 78196-90-4 Ethyl (5-phenyl-2-thienyl)(2-thienyl)glycolate 
• 344264-77-3 2-thienylglyoxylate phenylhydrazone 
• 80387-75-3 N-(2,6-dimethylphenyl)-2-thienylglyoxylic acid hydrazide 
• 345227-01-2 2,6-dimethylphenylhydrazone of 2-thienylglyoxylate 
• 89481-60-7 ethyl 2-(4-methoxyphenylimino)-2-(thiophen-2-yl)acetate 
• 4746-63-8 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid 
• 78196-89-1 (5-Phenyl-2-thienyl)(2-thienyl)acetic acid 
• 4408-82-6 2,2-di(thiophen-2-yl)acetic acid 
• 28560-51-2 2-hydroxy-2-phenyl-2-(thiophen-2-yl)acetic acid 
• 89008-59-3 2-Hydroxy-3-phenyl-2-(2-thienyl)propansaeure 
• 64471-60-9 2-Cyclohexyl-2-(2-thienyl)glykolsaeure 

Relevant academic research and scientific papers

Stereoselective Synthesis of Dihydrocoumarins via [1,2]-Phospha-Brook Rearrangement in Three-Component Coupling Reaction of α-Ketoesters, o-Quinone Methides, and Dialkyl Phosphites

A highly regio- and diastereoselective approach for the synthesis of phosphate substituted dihydrocoumarins via Br?nsted base catalyzed [1,2]-phospha-Brook rearrangement is reported. The two-step, one-pot Michael addition of α-phosphonyloxy enolates proceeds by coupling of dialkyl phosphite and α-ketoesters to o-quinone methides, followed by an intramolecular cyclization, providing 3,4-dihydrocoumarin frameworks.

Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes

A diverse reactivity of diazo compounds with nitrosoarene in an oxygen-transfer process and a formal [2 + 2] cycloaddition is reported. Nitosoarene has been exploited as a mild oxygen source to oxidize an in situ generated carbene intermediate under visible-light irradiation. UV-light-mediated in situ generated ketenes react with nitosoarenes to deliver oxazetidine derivatives. These operationally simple processes exemplify a transition-metal-free and catalyst-free protocol to give structurally diverse α-ketoesters or oxazetidines.

Chemo- And diastereoselective synthesis of pyrrolidines from aroylformates and δ-tosylamino enones via P(NMe2)3-mediated reductive amination/base-catalyzed michael addition cascade

A novel P(NMe2)3-mediated tandem (1 + 4) annulation between aroylformates and δ-tosylamino enones has been developed that affords a facile synthesis of functionalized pyrrolidines in moderate to excellent yields with exclusive chemoselectivity and high diastereoselectivity. Mechanistic investigation reveals that the reaction proceeds through an unprecedented P(NMe2)3-mediated reductive amination/base-catalyzed Michael addition cascade. The reaction herein also represents the first study of the reactivity patterns of the Kukhtin-Ramirez adducts toward ambiphilic nucleophile-electrophiles.

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers

The synthesis of chiral fluorine containing motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation of readily available vinyl fluorides. Various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups were found to be compatible with the reaction and provide the highly desirable product as single diastereomers with excellent enantioselectivities.

α-Alkoxycarbonyl-α-hydroxy secondary amides from a carbamoylsilane and α-ketoesters

The addition of N-methoxymethyl-N-organylcarbamoyl(trimethyl)silane to α-ketoesters in anhydrous toluene at 60 °C afforded α-alkoxycarbonyl-α-siloxy amides in high yields (75–96%). The methoxymethyl was used as an amino protecting group and could be easily converted into hydrogen atom by simple acid hydrolysis leading to α-alkoxycarbonyl-α- hydroxy secondary amides.

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds

A highly enantioselective hydrosilylation of 1,2-dicarbonyl compounds was successfully realized for the first time utilizing the combination of tricyclohexylphosphine and chiral alkenylborane derived in situ from diyne as a frustrated Lewis pair catalyst. A variety of optically active α-hydroxy ketones and esters were obtained in 52-98% yields with 86-99% ee's.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

Catalytic formal cycloadditions between anhydrides and ketones: Excellent enantio and diastereocontrol, controllable decarboxylation and the formation of adjacent quaternary stereocentres

It has been shown for the first time that enolisable anhydrides can participate in highly efficient and diastereo/enantioselective additions to activated ketones. In these reactions the anhydride component formally acts (initially) as the nucleophilic component. These processes are promoted by novel, readily prepared urea-substituted cinchona alkaloid-derived catalysts at low loadings under mild conditions. Three classes of enolisable anhydride and three different types of activated ketone were shown to be compatible with the process-generating a diverse range of structurally distinct and densely functionalised lactone products with the formation of two new stereocentres, one of which is quaternary. In one example, a product incorporating two contiguous quaternary stereocentres (one all carbon) was formed with outstanding enantiocontrol. It has been shown in the case of glutaconic anhydride derivatives that the cycloaddtion process is reversible, and can be accompanied by decarboxylation and olefin isomerisation. Reaction conditions can be modified to give access to three types of product with good-excellent ee.

Development of a simple system for the oxidation of electron-rich diazo compounds to ketones

Mild heating of diazo compounds in DMSO furnishes ketone products in moderate to excellent yields. The reaction is particularly effective on electron-rich substrates and exhibits high chemoselectivity, allowing for the use of diazo compounds containing additional oxidation-prone functional groups. This straightforward protocol offers an alternate route to synthetically useful α-ketoesters from readily available aryl diazoacetates.