1813-94-1

Usage

Uses

Ethyl 4-Fluorophenylglyoxylate (cas# 1813-94-1) is a compound useful in organic synthesis.

InChI:InChI=1/C10H9FO3/c1-2-14-10(13)9(12)7-3-5-8(11)6-4-7/h3-6H,2H2,1H3

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 
• 462-06-6 fluorobenzene 
• 4755-77-5 Ethyl oxalyl chloride 
• 1765-93-1 4-fluoroboronic acid 
• 623-49-4 ethyl cyanoformate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 64-17-5 ethanol 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 762-04-9 Diethyl phosphonate 
• 403-32-7 (4-fluorophenyl)glyoxal 
• 352-34-1 4-fluoro-1-iodobenzene 
• 405-50-5 p-Fluorophenylacetic acid 
• 587-88-2 ethyl 2-(4-fluorophenyl)acetate 

Downstream Products

• 1743-82-4 Cyclohexyl-(4-fluor-phenyl)-glykolsaeure-aethylester 
• 78587-63-0 [3-(4-Fluoro-phenyl)-2-oxo-2H-benzo[1,4]oxazin-6-yl]-acetic acid methyl ester 
• 78587-69-6 2-[3-(4-Fluoro-phenyl)-2-oxo-2H-benzo[1,4]oxazin-6-yl]-propionic acid methyl ester 
• 175543-23-4 ethyl α,α-difluoro-α-(p-fluorophenyl)acetate 
• 213479-90-4 (S)-(+)-1-(4-fluorophenyl)-1,2-ethanediol 
• 1040543-11-0 ethyl 3-{(2Z)-2-[2-(ethyloxy)-1-(4-fluorophenyl)-2-oxoethylidene]hydrazino}-3-oxopropanoate 
• 1080671-46-0 ethyl 2-(3-bromopropylimino)-2-(4-fluorophenyl)acetate 
• 1068161-69-2 C₁₅H₁₂F₂N₂O₂ 
• 1187487-80-4 ethyl 2-(4-fluorophenyl)-2-(4-methoxyphenylimino) acetate 
• 1057221-63-2 3-(4-fluorophenyl)quinoxalin-2(1H)-one 
• 1255772-31-6 3-(4-fluorophenyl)-2H-benzo[b][1,4]oxazin-2-one 
• 1223562-88-6 (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl (4-fluorophenyl)(oxo)acetate 
• 1282521-53-2 ethyl (S)-2-[bis(2-methoxyphenyloxy)phosphinyloxy]-2-(4-fluorophenyl)acetate 
• 1282521-64-5 ethyl (R)-2-[bis(2-methoxyphenyloxy)phosphinyloxy]-2-(4-fluorophenyl)acetate 

Relevant academic research and scientific papers

Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters

Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re

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.

Copper on charcoal: Cu0nanoparticle catalysed aerobic oxidation of α-diazo esters

By using a charcoal supported nano Cu0catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse the reaction of aryl α-diazo ester with water to form aryl ketoester, 2-aryl-2-hydroxyl acetate ester and 2-aryl acetate ester. In this case, water is split by α-diazo ester, and the diazo group is displaced by the oxygen or hydrogen atom in water. Mechanistic investigation showed that the reaction of α-diazo ester with oxygen proceeds through a radical pathway. In the presence of 2,2,6,6-tetramethyl piperidine nitrogen oxide, the reaction of α-diazo ester with oxygen is dramatically inhibited. Furthermore, the reaction of α-diazo ester with water is investigated by an isotopic tracer method, and GCMS detection showed that a disproportionation reaction occurred between α-diazo ester and water.

Copper(I)-catalyzed aerobic oxidation of α-diazoesters

A practical Cu-catalyzed oxidation of α-diazoesters to α-ketoesters using molecular oxygen as an oxidant has been developed. Both electron-poor and electron-rich aryl α-diazoesters are suitable substrates and provide the α-ketoesters in good yields. In this oxidative system, α-diazo-β-ketoesters are also compatible as substrates but unexpectedly furnish α-ketoesters via C-C bond cleavage, rather than the vicinal tricarbonyl products.

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

Novel quinoline derivative inhibitor

The invention provides a novel quinoline derivative inhibitor, which has a structure represented by the following general formula (I). According to the invention, the compound provided by the invention can selectively inhibit tyrosine kinase TAM family/an

Green preparation method of aryl [alpha]-keto ester compound

The invention discloses a green preparation method of an aryl [alpha]-keto ester compound. The method comprises the specific steps that an [alpha]-diazo compound serves as a reaction raw material, copper sulfate serves as a catalyst, water serves as a solvent, a target product aryl [alpha]-keto ester compound is prepared through a reaction at the temperature of 60 DEG C, the structural general formula of the [alpha]-diazo compound is shown in the specification, and the structural general formula of the correspondingly prepared target product aryl [alpha]-keto ester compound is shown in the specification. The method for synthesizing the target product aryl [alpha]-keto ester compound by catalyzing the [alpha]-diazo compound derivative with copper sulfate has the advantages that the reactioncondition is green and mild, the catalyst is cheap and easy to obtain, the operation is simple and convenient, the yield is relatively high, the universality of a reaction substrate is wide, and thelike.

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.

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization

Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.

Template-Directed Synthesis of Photocatalyst-Encapsulating Metal-Organic Frameworks with Boosted Photocatalytic Activity

In the past decade, the use of visible light to promote organic transformations has gained intense attention. In this study, we developed a template-directed synthesis method to use homogeneous Ru and Ir photocatalysts as structure-directing templates and succeeded to prepare a series of photocatalyst-encapsulating metal-organic frameworks (photocatalyst@MOFs) with zeolite-like structures. The open channels and polyhedral cages of MOFs effectively dispersed the encapsulated photocatalysts and facilitated the transport of reactants and products, leading to boosted catalytic activity and good reusability toward important organic reactions such as aerobic oxidation reaction of benzyl halides and the cyclization of tertiary anilines and maleimides under visible light. Moreover, we also demonstrate the versatility and universality of our templating strategy. It not only can form MOFs which cannot be accessed by other synthesis methods, but also can encapsulate various commercially available homogeneous photocatalysts into MOFs. This work explores an avenue to prepare heterogeneous photocatalysts to catalyze value-added reactions.