40061-54-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-(2-CHLOROPHENYL)ACETATE is used as a synthetic intermediate for the preparation of clotrimazole analogs with antimalarial activities. These analogs are designed to target and inhibit the growth of Plasmodium parasites, which are responsible for causing malaria.
ETHYL 2-(2-CHLOROPHENYL)ACETATE is also used as a synthetic intermediate for the preparation of non-nucleoside adenosine kinase inhibitors of aminoarylarylethynylpyrimidines. These inhibitors play a crucial role in the development of novel therapeutic agents for the treatment of various diseases, including cancer and other adenosine-related disorders.

Synthesis Reference(s)

Synthetic Communications, 20, p. 2631, 1990 DOI: 10.1080/00397919008051471

InChI:InChI=1/C10H11ClO2/c1-2-13-10(12)7-8-5-3-4-6-9(8)11/h3-6H,2,7H2,1H3

Upstream product

• 64-17-5 ethanol 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 694-80-4 2-bromo-1-chlorobenzene 
• 681-94-7 ethyl 2-(tributylstannyl)acetate 
• 75280-08-9 ethyl α-methylthio-(o-chlorophenyl)acetate 
• 108-90-7 chlorobenzene 
• 541-41-3 chloroformic acid ethyl ester 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 623-49-4 ethyl cyanoformate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 623-73-4 diazoacetic acid ethyl ester 
• 1071-46-1 hydrogen ethyl malonate 
• 346656-42-6 2-(2-chlorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 609-65-4 o-chlorobenzoyl chloride 

Downstream Products

• 85150-76-1 1,3-bis(2-chlorophenyl)propan-2-one 
• 19819-95-5 2-(2-chlorophenyl)-1-ethanol 
• 57543-09-6 1-(3',4'-Dimethoxyphenyl)-1-cyan-3-(2'-chlorphenyl)-propanon-2 
• 926008-66-4 {4-[6-chloro-5-(2-chlorophenyl)pyrimidin-4-ylethynyl]phenyl}dimethylamine 
• 3974-17-2 4,6-dichloro-5-(2-chlorophenyl)pyrimidine 
• 3974-13-8 5-(2-chlorophenyl)pyrimidine-4,6-diol 
• 83177-55-3 1-(o-Chlorophenyl)-3-azabicyclo[3.1.0]hexane 
• 66504-74-3 1-(o-chlorophenyl)-1,2-cyclopropanedicarboximide 
• 66504-73-2 (1R,2S)-1-(2-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 77053-65-7 (1R,2S)-1-(2-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 57543-10-9 1-(3',4'-Dimethoxyphenyl)-3-(4'-chlorphenyl)-propanon-2 
• 57543-32-5 1-(3',4'-Dimethoxyphenyl)-3-(2'-chlorphenyl)-2-acetamidopropan 
• 57543-11-0 1-(3',4'-Dimethoxyphenyl)-3-(2'-chlorphenyl)-2-aminopropan 
• 57543-12-1 1-(3',4'-Dimethoxyphenyl)-3-(4'-chlorphenyl)-2-formamidopropan 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists

A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.

Rapid Assembly of Saturated Nitrogen Heterocycles in One-Pot: Diazo-Heterocycle “Stitching” by N–H Insertion and Cyclization

Methods that provide rapid access to new heterocyclic structures in biologically relevant chemical space provide important opportunities in drug discovery. Here, a strategy is described for the preparation of 2,2-disubstituted azetidines, pyrrolidines, pi

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.

Mechanistic studies on gold-catalyzed direct arene c-h bond functionalization by carbene insertion: The coinage-metal effect

The catalytic functionalization of the Csp2-H bond of benzene by means of the insertion of the CHCO2Et group from ethyl diazoacetate (N2= CHCO2Et) has been studied with the series of coinage-metal complexes IPrMCl (IPr = 1,3-bis- (diisopropylphenyl)imidazol-2-ylidene) and NaBArF 4 (BArF 4 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate). For Cu and Ag, these examples constitute the first use of such metals toward this transformation, which also provides ethyl cyclohepta-2,4,6-trienecarboxylate as a byproduct from the so-called Buchner reaction. In the case of methyl-substituted benzenes, the reaction exclusively proceeds onto the aromatic ring, the Csp3-H bond remaining unreacted. A significant coinage-metal effect has been observed, since the gold catalyst favors the formation of the insertion product into the Csp2-H bond whereas copper and silver preferentially induce the formation of the cycloheptatriene derivative. Experimental studies and theoretical calculations have explained the observed selectivity in terms of the formation of a common Wheland intermediate, resembling an electrophilic aromatic substitution, from which the reaction pathway evolves into two separate routes to each product.

Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis

We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.

One-Pot Base-Mediated Synthesis of Functionalized Aza-Fused Polycyclic Quinoline Derivatives

A new one-pot protocol has been developed for the facile and efficient synthesis of aza-fused polycyclic quinolines (e.g., pyrrolo[1,2-a]quinolines) by the base-catalyzed reaction of 2-formylpyrroles and 2-halophenylacetonitriles. This reaction proceeded under transition metal-free conditions and showed high functional group tolerance, with the desired products being formed in good yields.

MULTIPLE KINASE PATHWAY INHIBITORS

Kinase with inhibitory activity against kinases disposed in multiple signaling pathways and their therapeutic uses.

Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities

It's all relative: A practical and efficient PdII-catalyzed regio- and chemoselective chlorination/bromination has been developed for the facile synthesis of a broad range of aromatic chlorides. The reaction demonstrates excellent reactivity, good functional-group tolerance, and high yields. A preliminary study was conducted to evaluate relative directing-group abilities of various functionalities. Copyright