64229-97-6

Upstream product

• 874-23-7 2-acetylcyclohexanone 

Downstream Products

• 16112-10-0 1-(cyclopent-1-en-1-yl)ethanone 

Relevant academic research and scientific papers

Synthesis method of beta-chloro-alpha, gamma-dicarbonyl compound

The invention relates to the technical field of chemical synthesis, and particularly discloses a synthesis method of a beta-chloro-alpha, gamma-dicarbonyl compound. The synthesis method comprises thefollowing steps: under a solvent-free condition, taking an alpha, gamma dicarbonyl compound shown as a formula (I) as a raw material, taking anhydrous aluminum chloride as a catalyst, and introducingchlorine to carry out chlorination reaction, so as to obtain the beta-chlorinated alpha, gamma dicarbonyl compound shown as a formula (II). The beta-chloro-alpha, gamma-dicarbonyl compound shown in the formula (II) is prepared through a chlorination reaction by taking chlorine as a chlorination reagent and taking anhydrous aluminum chloride as a catalyst under a solvent-free condition, a product with the purity of more than 90% can be obtained only through simple post-treatment of a reaction product, the yield can reach 90% or above. The method has the advantages of mild reaction conditions, simple process operation, no generation of sulfur dioxide polluting the environment, greenness, environmental protection, and suitableness for large-scale industrial production.

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

Unified strategy for Iodine(III)-Mediated Halogenation and azidation of 1,3-Dicarbonyl compounds

A mild and rapid (diacetoxyiodo)benzene-mediated formal electrophilic a-azidation of 1,3-dicarbonyl compounds using commercially available Bu 4NN3 as the azide source is reported. The reaction conditions employed are based on optimization studies conducted on the analogous halogenations with Et4NX (X = Cl, Br, I).

Sulfoxide-mediated Umpolung of alkali halide salts

A new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows the electrophilic halogenation of carbonyl compounds as well as halolactonisation reactions to proceed from the corresponding sodium salts, at room temperature and under mild conditions.

Hydrogen peroxide or peracetic acid mediated self-titrating α-halogenation of 1,3-dicarbonyl compounds

Efficient oxidative -halogenation of 1,3-dicarbonyl compounds has been achieved by employing a system comprising of sub-stoichiometric amounts of TiX4 (X = Cl, Br) in conjunction with environmentally benign hydrogen peroxide (H2Osub

Umpolung of halide reactivity: Efficient (diacetoxyiodo)benzene-mediated electrophilic α-halogenation of 1,3-dicarbonyl compounds

An efficient high-yielding (diacetoxyiodo)benzene-mediated α-halogenation of 1,3-dicarbonyl compounds utilising titanium tetrahalides as the halide source has been developed. The Royal Society of Chemistry 2009.

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.

Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions

Several aryl substituted ketones, cyclic ketones, 1,3-diketones and a β-ketoamide were halogenated with N-halosuccinimides under solvent-free reaction conditions (SFRC) at various temperatures (20-80 °C), whereas less enolized ketones required the presence of an acid catalyst (p-toluenesulfonic acid, PTSA). Bromination of substituted acetophenones obeys first order kinetics v=kBr[ketone] and the following correlation with the keto-enol equilibrium constant: log kBr=0.3pKE+C1, less enolized substrates being more reactive; the moderate positive charge developed in the rate determining step was confirmed by the Hammett correlation (ρ=-0.5). On the other hand, in cyclic ketones an opposite relation was observed: log kBr=-0.6pKE+C2, indicating higher reactivity of substrates with higher enolization constant (KE). The important role of the nature of the solvent (MeCN, MeOH) in preorganization of the ketone-NBS-PTSA mixture prior to SFRC bromination was found.

2-Chloropyridazin-3(2H)-ones as electrophilic chlorinating agents: Effective α-chlorination of active methylene/methine compounds

2,4,5-Trichloro- (2a) and 2,4-dichloro-5-methoxypyridazin-3(2H)-one (2b) are novel electrophilic chlorinating agents. α-Chlorination of active methylene/methine compounds with 2 in the presence of either Lewis or protonic acids in dichloromethane (for Lewis acid) or water (for protonic acid or none) at room temperature gave also selectively α-monochlorides and/or α,α-dichlorides in good to excellent yields.