27700-44-3

Upstream product

• 2648-61-5 2,2-dichloroacetophenone 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 3034-94-4 3-nitrophenylacetylene 
• 64-19-7 acetic acid 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 201206-09-9 (Z)-2,2-Dichloro-1-(3-nitrophenyl)ethanone oxime 
• 1602827-73-5 2,2-dichloro-1-(3-nitrophenyl)ethanol 
• 1588766-70-4 (S)-2,2-dichloro-1-(3-nitrophenyl)ethanol 
• 1588766-66-8 (R)-2,2-dichloro-1-(3-nitrophenyl)ethanol 

Relevant academic research and scientific papers

Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships

Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.

A simple, mild, and efficient method for the preparation of α,α-dichloroketones with DCDMH catalyzed by ammonium chloride

New process that can selectively prepare α,α-dichloro ketones from various ketones with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using ammonium chloride as a catalyst is reported. The effects of ammonium salts, solvents, DCDMH, and reaction temperature were investigated. Under the optimal condition, most of α,α-dichlorinated products were selectively obtained in 86-98% yield.

Expanding the scope of alcohol dehydrogenases towards bulkier substrates: Stereo- and enantiopreference for α,α-dihalogenated ketones

Alcohol dehydrogenases (ADHs) were identified as suitable enzymes for the reduction of the corresponding α,α-dihalogenated ketones, obtaining optically pure β,β-dichloro- or β,β-dibromohydrins with excellent conversions and enantiomeric excess. Among the different biocatalysts tested, ADHs from Rhodococcus ruber (ADH-A), Ralstonia sp. (RasADH), Lactobacillus brevis (LBADH), and PR2ADH proved to be the most efficient ones in terms of activity and stereoselectivity. In a further study, two racemic α-substituted ketones, namely α-bromo- α-chloro- and α-chloro-α-fluoroacetophenone were investigated to obtain one of the four possible diastereoisomers through a dynamic kinetic process. In the case of the brominated derivative, only the (1R)-enantiomer was obtained by using ADH-A, although with moderate diastereomeric excess (>99 % ee, 63 % de), whereas the fluorinated ketone exhibited a lower stereoselectivity (up to 45 % de). Bulking up: A series of β,β-dihalohydrins are obtained through alcohol dehydrogenase (ADH) catalyzed bioreduction of the synthesized α,α-dihalogenated ketones. Two racemic acetophenone derivatives are also subjected to this protocol to obtain stereoenriched alcohols through dynamic kinetic resolution (DKR).

Laccase/TEMPO-mediated system for the thermodynamically disfavored oxidation of 2,2-dihalo-1-phenylethanol derivatives

An efficient methodology to oxidize β,β-dihalogenated secondary alcohols employing oxygen was achieved in a biphasic medium using the laccase from Trametes versicolor/TEMPO pair, providing the corresponding ketones in a clean fashion under very mild conditions. Moreover, a chemoenzymatic protocol has been applied successfully to deracemize 2,2-dichloro-1-phenylethanol combining this oxidation with an alcohol dehydrogenase-catalyzed bioreduction. the Partner Organisations 2014.

The use of sodium chlorate/hydrochloric acid mixtures as a novel and selective chlorination agent

Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the α-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.

Simple and efficient methods for selective preparation of α-mono or α,α-dichloro ketones and β-ketoesters by using DCDMH

New processes that can selectively prepare α-mono or α,α-dichloro ketones and β-ketoesters using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) are reported. Using silica gel as the catalyst and methanol as the solvent and heating for 1 h under reflux, α-monochlorinated products were selectively obtained in 86-98% yield. However using a deep eutectic solvent (choline chloride: p-TsOH = 1:1) as the solvent and stirring for 45 min at room temperature, α,α- dichlorinated products were selectively obtained in 86-95% yield.

A convenient and efficient synthesis of 1-aryl-2,2-dichloroethanones

1-Arylethanones are readily chlorinated with an aqueous HCl-H 2O2 system using ethanol as a cosolvent. The reaction prceeds rapidly and results in selective conversion of 1-arylethanones into 1-aryl-2,2-dichloroethanones in yields of 48-89%, depending on the nature of the substituent in the aryl group.

Reactions of 1-aryl-2,2-dihalogenoethanone oximes with tetrasulfur tetranitride (S4N4): A general method for the synthesis of 3-aryl-4-halogeno-1,2,5-thiadiazoles

1-Aryl-2,2-dichloro-7, 1-aryl-2,2-dibromo-8, 1-aryl-2-bromo-2-fluoro-9 and 1-aryl-2-chloro-2-fluoroethanone oximes 10 have been prepared by allowing the corresponding ketones to react with hydroxylamine hydrochloride in EtOH at room temperature. Stereoche

Ozone-mediated Nitration of Aromatic Ketones and Related Compounds with Nitrogen Dioxide

Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give ortho- and meta-nitro derivatives as the principal products, the former usually being predominant (ortho:meta = 1.1-3.8:1.0).No attack was observed on the alkyl side chains.

Halogenation Using Quaternary Ammonium Polyhalides. XXXII. Dichlorination of Aromatic Acetyl Derivatives with Benzyltrimethylammonium Tetrachloroiodate

The reaction of aromatic acetyl derivatives with 2 molar amounts of benzyltrimethylammonium tetrachloroiodate in acetic acid at 70 deg C for several hours gave dichloroacetyl derivatives in good yields.