63131-29-3

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-FLUOROBENZOYLACETATE is used as a key intermediate in the synthesis of various drug candidates for the treatment of different diseases. Its unique molecular structure allows for the development of novel compounds with potential therapeutic applications.
Used in Synthesis of 3-amino-4-(4-fluoro-phenyl)furans:
METHYL 4-FLUOROBENZOYLACETATE is used as a starting material in the synthesis of 3-amino-4-(4-fluoro-phenyl)furans, which are a series of compounds with potential applications in various fields, including pharmaceuticals and materials science.
Used in Synthesis of Substituted Coumarin Derivatives:
METHYL 4-FLUOROBENZOYLACETATE is used as a reactant in the synthesis of substituted coumarin derivatives. These compounds have potential as 5-lipoxygenase inhibitors, which are important targets for the development of anti-inflammatory and anti-allergy drugs.

InChI:InChI=1/C10H9FO3/c1-14-10(13)6-9(12)7-2-4-8(11)5-3-7/h2-5H,6H2,1H3

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 616-38-6 carbonic acid dimethyl ester 
• 456-22-4 4-Fluorobenzoic acid 

Downstream Products

• 63131-00-0 C₁₄H₁₈FO₄PS 
• 1001922-15-1 2-bromo-3-(4-fluorophenyl)-3-oxopropionic acid methyl ester 
• 885123-33-1 (R)-3-(4-fluorophenyl)-3-hydroxypropionic acid methyl ester 
• 434957-05-8 methyl (Z)-3-acetamido-3-(4-fluorophenyl)-2-propenoate 
• 757951-21-6 methyl (Z)-3-amino-3-(4-fluorophenyl)acrylate 
• 106015-74-1 3-(4-fluorophenyl)-3-oxo-N-phenylpropanamide 
• 99817-27-3 3-amino-4-(4-fluorophenyl)furazane 
• 17628-74-9 p-fluorophenylglyoxalmonoxime 
• 850881-86-6 4-(4-fluorophenyl)-7-hydroxy-2H-chromen-2-one 
• 202859-08-3 3-amino-3-(para-fluorophenyl)-acrylic acid methyl ester 
• 80646-00-0 3-(4-fluorophenyl)-3-oxopropanoic acid 
• 135833-85-1 1-(4-fluorophenyl)-3-phenyl-5-methylhexane-1,4-dione 
• 135833-86-2 5-(4-fluorophenyl)-2-(1-methylethyl)-3-phenyl-1H-pyrrole-1-propanal 

Relevant academic research and scientific papers

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

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.

An efficient route for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives promoted by CBr4 in one pot

A metal-free one-pot method for the synthesis of N-(1H-benzo[d]imidazol-2-yl)benzamide derivatives was proposed mediated by CBr4. The reaction went through ring formation and opening processes with only two protons leaving and the thermodynamically favorable products were selectively formed in moderate to good yields.

Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides

We herein report a robust and safe palladium catalyzed domino-carbonylation/Suzuki–Miyaura cross-coupling reaction of vinyltosylates with arylboronic acids using Mo(CO)6 as CO-source. The derived γ-keto ester were subsequently cyclized under acidic conditions to obtain γ-hydroxybutenolides, an important structural motif, which occurs in biologically active natural products.

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.

Synthesis of novel proxyphylline derivatives with dual Anti-Candida albicans and anticancer activity

Three out of 16 newly synthesized 1,3-dimethylxanthine derivatives (proxyphylline analogues) exhibited consistencies between antifungal and anticancer properties. Proxyphylline possessing 1-(10H-phenothiazin-10-yl)propan-2-yl (6) and polybrominated benzimidazole (41) or benzotriazole moiety (42) remained selectively cidal against Candida albicans (lg R ≥ 3 at conc. of 31, 36 and 20 μM, respectively) however not against normal mammalian Vero cell line in vitro (IC50 ≥ 280 μM) and Galleria mellonella in vivo. These compounds also displayed moderate antineoplastic activity against human breast adenocarcinoma (MCF-7) cell line (EC50 = 80 μM) and high against peripheral blood T lymphoblast (CCRF-CEM) (EC50 = 6.3–6.5 μM). In addition, 6 and 42 exerted: (1) dual activity against fungal adhesion and damage mature biofilm; (2) necrosis of planktonic cells due to loss of membrane function and of structural integrity; (3) biochemical (inhibition of sessile cell respiration) and morphological changes in cell wall polysaccharide contents. Therefore, leading proxyphylline derivatives can be employed to prevent cancer-associated biofilm Candida infections.

PhIO/Et3N ? 3HF-Mediated Formation of Fluorinated 2H-Azirines via Domino Fluorination/Azirination Reaction of Enamines

A variety of enamine carboxylic esters and enaminones were converted to the biologically interesting fluorinated 2H-azirines through reactions with PhIF2 generated in situ by PhIO and Et3N ? 3HF in 1,2-dichroloethane, which features the hypervalent iodine reagents-mediated introduction of fluorine atom and formation of the 2H-azirine skeleton under metal-free conditions. The domino reaction is postulated to proceed via a PhIF2-mediated oxidative fluorination and a subsequent azirination of the fluorinated enamine intermediates. (Figure presented.).

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.

Rhodium-Catalyzed Enantioconvergent Isomerization of Homoallylic and Bishomoallylic Secondary Alcohols

We present herein an unprecedented enantioselective isomerization of homoallylic and bishomoallylic secondary alcohols, catalyzed by a commercially available rhodium-complex and a base. This catalytic redox-neutral process provides an effective access to chiral ketones in high efficiency and enantioselectivity, without the use of any stoichiometric reagent or generation of any waste. For the reaction of homoallylic alcohols, this system achieved not only a stereoconvergent access to chiral ketones bearing a β-stereocenter (up to 95%, 86% ee) but also a concomitant oxidative kinetic resolution of the alcohol substrates (S > 20). In the case of bishomoallylic alcohols, an intriguing ligand-induced divergent reactivity was observed. A terminal-to-internal alkene isomerization promoted by Rh/L7 followed by redox isomerization using Rh/BINAP system produced chiral ketones bearing a γ-stereocenter with high yield and enantioselectivity. Mechanistic studies provided strong support for the redox-isomerization pathway with chain walking of the key alkyl-Rh intermediate.

Palladium-Catalyzed Enantioselective Narasaka–Heck Reaction/Direct C?H Alkylation of Arenes: Iminoarylation of Alkenes

A palladium-catalyzed reaction of γ,δ-unsaturated oxime esters with oxadiazoles afforded dihydropyrroles in good to excellent yields through an intramolecular iminopalladation/intermolecular direct heteroarene C?H alkylation cascade. This unprecedented iminoarylation of alkenes was subsequently realized in an enantioselective manner in the presence of a chiral bidentate phosphine ligand (Synphos).