25017-08-7

Usage

Chemical Properties

white to yellow crystalline low melting solid

InChI:InChI=1/C11H13ClO/c1-9(12)7-8-11(13)10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 3115-66-0 tetra-n-butylphosphonium iodide 
• 109-72-8 n-butyllithium 
• 104-88-1 4-chlorobenzaldehyde 
• 122-01-0 4-chloro-benzoyl chloride 
• 637-87-6 1-Chloro-4-iodobenzene 
• 638-29-9 n-valeryl chloride 
• 122334-37-6 4-chloro-N-methoxy-N-methylbenzamide 
• 13856-87-6 1-(p-chlorophenyl)-1-pentanol 
• 134573-99-2 1-(1-chloropentyl)-4-chlorobenzene 
• 201230-82-2 carbon monoxide 
• 1085430-51-8 2-(4-chlorophenyl)hexanamide 
• 106-39-8 bromochlorobenzene 
• 110-62-3 pentanal 

Downstream Products

• 109249-67-4 Butyl-hexyl-<4-chlor-phenyl>-carbinol 
• 144741-87-7 1-(p-chlorophenyl)-1-n-butyl epoxide 
• 91428-38-5 α-<4-Chlor-phenyl>-pentylamin 
• 13856-87-6 1-(p-chlorophenyl)-1-pentanol 
• 1019113-44-0 tert-butyl 4-[1-(4-chlorobenzoyl)butyl]benzoate 
• 820971-74-2 methyl {1-[1-(4-chlorophenyl)ethyl]azetidin-3-yl}(3,5-difluorophenyl)acetate 
• 132104-23-5 -heptyl-<4-chlor-phenyl>-methan 

Relevant academic research and scientific papers

Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water

Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.

A Highly Efficient Dimeric Manganese-Catalyzed Selective Hydroarylation of Internal Alkynes

We have developed a general and site-predictable manganese-catalyzed hydroarylation of internal alkynes in the presence of water, under an air atmosphere without the involvement of ligand. The unique catalytic feature of this reaction is highlighted by comparison with other widely used transition metal catalysts including palladium, rhodium, nickel, or copper. The simple operation, high efficiency and excellent functional group compatibility make this protocol practical for more than 90 structurally diverse internal alkynes, overcoming the influence of both electronic and steric effect of alkynes. Its exclusive regio- and chemoselectivity originates from the unique reactivity of the manganese-based catalyst towards an inherent double controlled strategy of sterically hindered propargyl alcohols without the installing of external directing groups. Its synthetic robustness and practicality have been illustrated by the concise synthesis of bervastatin, a hypolipidemic drug, and late-stage modification of complex alkynes with precise regioselectivity.

A simple synthesis of ketone from carboxylic acid using tosyl chloride as an activator

An effective process for the conversion of carboxylic acid to ketone has been discovered. In this process, carboxylic acid has been activated using p-toluene sulphonyl group. Under the optimized condition, aromatic, aliphatic heteroaromatic carboxylic acids have been proved to be good substrates for this methodology. The byproduct of this reaction can be removed very easily during work up process. Also, one equivalent of organometallic reagent is sufficient to complete this transformation.

Directed: Ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: The organolithium base dictates the chemoselectivity

Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki-Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.

Simple one pot synthesis of ketone from carboxylic acid using DCC as an activator

Simple one pot procedure for the conversion of carboxylic acid to ketone is described. Various carboxylic acids were converted to the corresponding ketones in excellent manner in presence of N,N′-dicyclohexylcarbodiimide (DCC) and organometallic reagents. Aromatic, heteroaromatic and aliphatic acids were converted to the corresponding ketones smoothly under the optimum conditions using organolithium reagents. In this process, desired products have been isolated from the crude reaction mixtures in moderate yields during the purification process.

Pd-catalyzed Oxidative Cross-coupling of Alkyl Chromium(0) Fischer Carbene Complexes with Organoboronic Acids

Alkyl chromium(0) carbene complexes have been explored as the cross-coupling partners in the palladium-catalyzed reaction with aryl or alkenyl boronic acids. This coupling reaction displays the versatile reactivities of alkyl chromium(0) carbenes under palladium catalysis. Mechanistically, this transformation is proposed to involve deprotonation of the alkyl chromium carbene substrate to generate a vinyl chromium anion intermediate that undergoes transmetalation to organopalladium species and reductive elimination.

A phosphine-free, heterogeneous palladium-catalyzed atom-efficient carbonylative cross-coupling of triorganoindiums with aryl halides leading to unsymmetrical ketones

The first phosphine-free heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl halides with triorganoindiums has been developed that proceeds smoothly under 1 or 2.5 atm of carbon monoxide in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable unsymmetrical ketones with high atom-economy, good yield, and recyclability of the catalyst. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

A phosphine-free, atom-efficient cross-coupling reaction of triorganoindiums with acyl chlorides catalyzed by immobilization of palladium(0) in MCM-41

The first phosphine-free heterogeneous palladium(0)-catalyzed cross-coupling of triorganoindiums with acyl chlorides has been developed that proceeds smoothly in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable aryl ketones and α,β-acetylenic ketones with high atom-economy and high yield. This phosphine-free heterogeneous palladium(0) catalyst can be easily prepared from commercially available reagents and recovered by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.

Aminothiazole derivatives

The invention relates to aminothiazole heterocyclic derivatives, a preparation method thereof and an application of the aminothiazole heterocyclic derivatives in preparation of drugs for treating or preventing progressive cognitive disorder and/or amnesia diseases.

Iron-Catalyzed Acylation of Polyfunctionalized Aryl- and Benzylzinc Halides with Acid Chlorides

FeCl2 (5 mol %) catalyzes a smooth and convenient acylation of functionalized arylzinc halides at 50 °C (2-4 h) and benzylic zinc chlorides at 25 °C (0.5-4 h) with a variety of acid chlorides leading to polyfunctionalized diaryl and aryl heteroaryl ketones.