212755-76-5

Usage

Chemical Properties

yellow crystalline powder

Uses

Methyl 4-trifluoromethylbenzoylacetate

InChI:InChI=1/C11H9F3O3/c1-17-10(16)6-9(15)7-4-2-3-5-8(7)11(12,13)14/h2-5H,6H2,1H3

Upstream product

• 79-20-9 acetic acid methyl ester 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 1271792-68-7 (R,Z)-methyl 3-(1-phenylethylamino)-3-(4-(trifluoromethyl)phenyl)acrylate 
• 1271792-66-5 (Z)-methyl 3-(benzylamino)-3-(4-(trifluoromethyl)phenyl)acrylate 
• 1271792-80-3 C₁₈H₁₈F₃NO₂ 
• 1228543-08-5 (R)-methyl 3-amino-3-(4-(trifluoromethyl)phenyl)propanoate 
• 1271792-83-6 C₁₉H₂₀F₃NO₂ 
• 1271793-24-8 (R)-4-(4-(trifluoromethyl)phenyl)azetidin-2-one 
• 1404446-93-0 3-(4-chlorobenzyl)-2-methyl-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one 

Relevant academic research and scientific papers

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis

Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.

Fluorous l -Carbidopa Precursors: Highly Enantioselective Synthesis and Computational Prediction of Bioactivity

New fluorous enantiopure (S)-α-aminated β-keto esters were prepared through a highly enantioselective electrophilic α-amination step in the presence of europium triflate and (R,R)-phenyl-pybox. These compounds are precursors of fluorinated analogues of l-

4, 6-diaryl pyran derivative and application thereof in preparation of liver cancer drugs

The invention relates to 4, 6-diaryl pyran derivative and application thereof in the preparation of liver cancer drugs. The 4, 6-diaryl pyran derivative as shown in general formula (I) and pharmaceutically acceptable salt, aquo-complex, solvate or optical isomer thereof have anti-tumor effect, and are particularly applied to the preparation of drugs for treating and/or preventing liver cancer. The compound has good antitumor drug development and application prospects.

Nickel-catalyzed enantioselective hydrogenation of β-(acylamino)acrylates: Synthesis of chiral β-amino acid derivatives

The nickel-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates has been developed, affording chiral β-amino acid derivatives with excellent yields (95-99% yield) and enantioselectivities (97-99% ee). With the Ni-Binapine system, high enantioselectivities (98-99% ee) have also been obtained in the hydrogenation of Z/E isomeric mixtures of β-alkyl and β-aryl β-(acylamino)acrylates. The synthesis of chiral β-amino acid derivatives on a gram scale has also been achieved with 0.2 mol % catalyst loading.

Regioselective Rhodium-Catalyzed Addition of β-Keto Esters, β-Keto Amides, and 1,3-Diketones to Internal Alkynes

The first rhodium-catalyzed regioselective addition of 1,3-dicarbonyl compounds, including β-keto esters, β-keto amides, and 1,3-diketones, to internal alkynes furnishes branched allylic compounds. By applying RhI/DPEphos/TFA as the catalytic system, aliphatic as well as aromatic internal methyl-substituted alkynes act as suitable substrates to yield valuable branched α-allylated 1,3-dicarbonyl compounds regioselectively in good to excellent yields. A simple basic saponification–decarboxylation procedure provides access to valuable γ,δ-unsaturated ketones. The reaction shows a broad functional-group tolerance, and numerous structural variations on both reaction partners highlight the synthetic potential and flexibility of this method.

Nickel-catalyzed asymmetric transfer hydrogenation of olefins for the synthesis of α- And β-amino acids

The field of asymmetric (transfer) hydrogenation of prochiral olefins has been dominated by noble metal catalysts based on rhodium, ruthenium, and iridium. Herein we report that a simple nickel catalyst is highly active in the transfer hydrogenation using

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams

A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.