7298-86-4

Upstream product

• 126-81-8 dimedone 
• 35024-12-5 (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 
• 7298-89-7 2-chloro-5,5-dimethyl-1,3-cyclohexanedione 
• 7722-84-1 dihydrogen peroxide 
• 1807-68-7 diazodimedone 
• 70990-68-0 2-chloro-3-hydroxy-5,5-dimethylcyclohex-2-enone 

Downstream Products

• 7298-89-7 2-chloro-5,5-dimethyl-1,3-cyclohexanedione 
• 102154-58-5 phosphoric acid diethyl ester-(2-chloro-5,5-dimethyl-3-oxo-cyclohex-1-enyl ester) 
• 17554-71-1 2,4-dichloro-5,5-dimethyl-cyclohexane-1,3-dione 
• 17554-72-2 4-Chlor-1.1-dimethyl-cyclohexan-trion-(2.3.5) 
• 75594-56-8 2,4-dichlorodimedone 
• 75594-65-9 2,2,4,4,6,6-hexachloro-5,5-dimethyl-1,3-cyclohexanedione 
• 126-81-8 dimedone 
• 21428-81-9 2,2,4,4-tetrachlorodimedone 
• 17257-68-0 2,2,4-trichlorodimedone 
• 75594-52-4 2-bromo-2,4-dichlorodimedone 
• 75594-57-9 2,4,4-trichlorodimedone 
• 343772-88-3 2,4,4,6-tetrachlorodimedone 
• 75594-54-6 2,2,4,4,6-pentachlorodimedone 
• 75594-60-4 2,2,4,6,6-pentachloro-5,5-dimethyl-3-cyclohexenone 

Relevant academic research and scientific papers

First detection of a chloroperoxidase in bryophytes

Chlorinated cyclic bisbibenzyls of the isoplagiochin type are the first verified halometabolites from bryophytes. They could be obtained by in vitro chlorination of isoplagiochin C with chloroperoxidase from Caldariomyces fumago. Furthermore, an enzyme of

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.

New syntheses of haloketo acid methyl esters and their transformation to halolactones by reductive cyclization

A new method for haloketo acid methyl ester synthesis on the basis of the ring-opening of cyclic α,β-unsaturated ketones followed by halogenation under mild conditions is reported. Di- and tri-haloketo acid methyl esters are conveniently synthesized via the hydrolytic ring-opening reaction through this method. Halolactones were readily obtained from these haloketo acid methyl esters by reductive cyclization employing NaBH4 and trifluoroacetic acid. Derivatizations of the obtained halolactone utilizing the exo-halomethylene moiety were also demonstrated.

Myeloperoxidase-mediated oxidation of edaravone produces an apparent non-toxic free radical metabolite and modulates hydrogen peroxide-mediated cytotoxicity in HL-60?cells

Edaravone is considered to be a potent antioxidant drug known to scavenge free radical species and prevent free radical-induced lipid peroxidation. In this study, we investigated the effect of edaravone on the myeloperoxidase (MPO) activity, an enzyme res

Characterization of a Cyanobacterial Haloperoxidase and Evaluation of its Biocatalytic Halogenation Potential

Vanadium-dependent haloperoxidases (VHPOs) are a class of halogenating enzymes found in fungi, lichen, algae, and bacteria. We report the cloning, purification, and characterization of a functional VHPO from the cyanobacterium Acaryochloris marina (AmVHPO), including its structure determination by X-ray crystallography. Compared to other VHPOs, the AmVHPO features a unique set of disulfide bonds that stabilize the dodecameric assembly of the protein. Easy access by high-yield recombinant expression, as well as resistance towards organic solvents and temperature, together with a distinct halogenation reactivity, make this enzyme a promising starting point for the development of biocatalytic transformations.

Efficient Synthesis of α-Chloroketones Catalyzed by Fluorous Hydrazine-1,2-Bis(Carbothioate) Organocatalyst

A novel and recoverable fluorous hydrazine-carbothioate organocatalyst was prepared. It could catalyze α-chlorination of alkyl ketones with N-chlorosuccinimide as chlorine source under mild reaction conditions. The reaction afforded the corresponding α-ch

Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene

Pre-formed phenyliodonium ylides of cyclic and acyclic β-diketones, β-keto esters and β-diesters were reacted with (dichloroiodo)benzene, resulting in transfer of both chloride ligands onto the ylidic carbon. These two hypervalent iodine(III) compounds exhibit high reactivity towards each other under mild reaction conditions and typically afford the gem-dichloride products in good yield. Upon comparison of these chlorination reactions with those of the analogous diazocarbonyl compounds, reactions of iodonium ylides were unilaterally faster, and often gave the products in higher yield.

Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene

Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.

Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds

The reaction of β-dicarbonyl compounds (β-ketoesters and β-diketones) with 0.34 mol equiv of trichloro- and tribromoisocyanuric acids produced regioselectively the corresponding α-monohalo β-dicarbonyl compound. On the other hand, utilization of 0.68 mol equiv of the trihaloisocyanuric acid produced the α,α-dihalo β-dicarbonyl compound.

An efficacious method for the halogenation of β-dicarbonyl compounds under mildly acidic conditions

A variety of 1,3-diketones, β-ketoesters and malonates can be chlorinated in high yields using sodium hypochlorite in a 5:2 mixture of acetone/acetic acid at 0°C for 1 h. Similarly, bromination of these dicarbonyl substrates can be accomplished under the same conditions using sodium hypobromite.