66644-67-5

Usage

InChI:InChI=1/C11H12O3/c1-3-14-11(13)10(12)9-7-5-4-6-8(9)2/h4-7H,3H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 5955-73-7 2-methylbenzoyl cyanide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 95-92-1 oxalic acid diethyl ester 
• 6957-89-7 Ethyl dichloro-(ethoxy)-acetate 
• 108-88-3 toluene 
• 16419-60-6 2-Methylphenylboronic acid 
• 623-49-4 ethyl cyanoformate 
• 529-20-4 2-methylphenyl aldehyde 
• 33872-80-9 o-tolyl magnesium chloride 
• 62281-72-5 ethyl hydroxy(2-methylphenyl)acetate 
• 577-16-2 2-Methylacetophenone 
• 35276-81-4 3-oxo-3-(o-tolyl)propanenitrile 
• 71315-64-5 2-nitro-1-(o-tolyl)ethan-1-one 

Downstream Products

• 62281-64-5 o-Tolyl-triethylsilanyloxy-acetic acid ethyl ester 
• 85905-80-2 (Dibutyl-ethyl-silanyloxy)-o-tolyl-acetic acid ethyl ester 
• 85905-72-2 [(Ethoxycarbonyl-o-tolyl-methoxy)-phenyl-silanyloxy]-o-tolyl-acetic acid ethyl ester 
• 85905-73-3 C₃₉H₄₄O₉Si 
• 211044-11-0 (S)-1-(2-methylphenyl)ethane-1,2-diol 
• 139093-41-7 (R)-1-(2-methylphenyl)ethane-1,2-diol 
• 62281-72-5 ethyl hydroxy(2-methylphenyl)acetate 
• 125602-39-3 ethyl 2-(bromomethyl)benzoylformate 
• 1086108-78-2 (Z)-ethyl 2-(4-methoxyphenylimino)-2-o-tolylacetate 
• 1068161-63-6 C₁₇H₁₈N₂O₂ 
• 1220306-89-7 C₁₄H₁₅NO₃ 
• 1254939-24-6 ethyl 2-hydroxy-2-o-tolylpent-4-enoate 
• 1339804-83-9 (Z)-ethyl 2-(2-acetoxy-6-methylphenyl)-2-(methoxyimino)acetate 
• 1339804-62-4 (Z)-ethyl 2-(methoxyimino)-2-o-tolylacetate 

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

Unraveling two pathways for NHPI-mediated electrocatalytic oxidation reaction

Two pathways for N-hydroxyphthalimide (NHPI)-mediated electrocatalytic oxidation using phenylacetate derivatives as template substrates were first reported for benzylic C[sbnd]H oxidation to oxygenated and non-oxygenated products. DFT calculation indicates that the hydrogen-atom transfer (HAT) process between phthalimido-N-oxyl (PINO) and substrate is a rate-determined step. Aromatic α-keto esters and 2-((1,3-dioxoisoindolin-2-yl)oxy)-2-aryl acetate obtained by cross-coupling between benzylic radical and PINO can be selectively synthesized through controlling the concentration of PINO radical. This method provides a deep understanding for selective weak C[sbnd]H oxidation using NHPI as redox mediator.

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.

General Synthesis of Chiral α,α-Diaryl Carboxamides by Enantioselective Palladium-Catalyzed Cross-Coupling

A general synthesis of chiral α,α-diaryl carboxamides is developed by enantioselective cross-coupling between 2-bromo-2-aryl carboxamides and arylboronic acids, leading to a series of chiral α,α-diaryl carboxamides with various electronic properties and functionalities in moderate to excellent enantioselectivities and yields. The employment of a sterically bulky chiral P,P═O ligand L2 is critical for the reactivity and selectivity. This protocol is applied to an efficient asymmetric synthesis of a key intermediate of dopamine receptor agonist SKF 38393.

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.

Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: Synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N2 or O2). A N2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O2 atmosphere results in the generation of α-ketoesters through the oxidative CC/C-O coupling pathway.

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.

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX-Ru as a chiral catalyst under 5 bar H2, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.

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.