2719-26-8

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxamide, N-phenylis used as an intermediate in the production of various pharmaceuticals for its ability to be incorporated into the molecular structure of different drugs, enhancing their therapeutic properties and effectiveness.
Used in Agrochemical Industry:
In the agrochemical industry, Cyclohexanecarboxamide, N-phenylis utilized as an intermediate in the synthesis of various agrochemicals, contributing to the development of more effective and targeted pest control solutions.
Used in Organic Synthesis:
Cyclohexanecarboxamide, N-phenylserves as a building block in the synthesis of other organic compounds, enabling the creation of a wide range of chemical products with diverse applications.
Used in Chemical Research:
Cyclohexanecarboxamide, N-phenylis also used in the field of chemical research, where it aids in the exploration of new chemical reactions, mechanisms, and the development of innovative synthetic methods.

InChI:InChI=1/C13H17NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h2,5-6,9-11H,1,3-4,7-8H2,(H,14,15)

Upstream product

• 23517-35-3 (Z)-cyclohexyl(phenyl)methanone oxime 
• 931-51-1 cyclohexylmagnesiumchloride 
• 103-71-9 phenyl isocyanate 
• 931-50-0 cyclohexylmagnesium bromide 
• 62-53-3 aniline 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 98-89-5 Cyclohexanecarboxylic acid 
• 4904-55-6 cyclohexanecarbonyl peroxide 
• 110-83-8 cyclohexene 
• 473440-42-5 cyclohexylcarbonyl 2-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)sulfide 
• 37881-06-4 3,5-dimethyl-pyrazole-1-carboxylic acid anilide 
• 60014-85-9 (1,1-dibromomethylene)cyclohexane 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 

Downstream Products

• 101090-33-9 2-cyclohexyLiDene-3-phenyl-oxazolidine-4,5-dione 
• 4664-73-7 1-Chlor-cyclohexan-1-carbonsaeure-anilid 
• 1262796-62-2 C₂₃H₂₃NO 
• 1360571-16-9 2,4-dichlorophenyl N-phenylcyclohexanecarboximidate 
• 91790-88-4 C₁₉H₂₂N₂ 
• 315712-37-9 N-(4-bromophenyl)-cyclohexanecarboxamide 
• 126541-71-7 N-cyclohexylmethyl-aniline; hydrochloride 
• 548763-46-8 N-(4-hydroxyphenyl)cyclohexanecarboxamide 
• 220383-46-0 N-(2-trifluoromethylphenyl)cyclohexanecarboxamide 
• 315712-26-6 N-(4-methoxyphenyl)-cyclohexanecarboxamide 
• 200706-63-4 N-(4-iodophenyl)cyclohexanecarboxamide 
• 1225638-93-6 2-(cyclohexyl)-4-phenylquinoline 

Relevant academic research and scientific papers

Copper-Catalyzed Carbonylative Coupling of Cycloalkanes and Amides

Carbonylation reactions are a most powerful method for the synthesis of carbonyl-containing compounds. However, most known carbonylation procedures still require noble-metal catalysts and the use of activated compounds and good nucleophiles as substrates.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Photocatalyzed Triplet Sensitization of Oximes Using Visible Light Provides a Route to Nonclassical Beckmann Rearrangement Products

Oximes are valuable synthetic intermediates for the preparation of a variety of functional groups. To date, the stereoselective synthesis of oximes remains a major challenge, as most current synthetic methods either provide mixtures of E and Z isomers or furnish the thermodynamically preferred E isomer. Herein we report a mild and general method to achieve Z isomers of aryl oximes by photoisomerization of oximes via visible-light-mediated energy transfer (EnT) catalysis. Facile access to (Z)-oximes provides opportunities to achieve regio- and chemoselectivity complementary to those of widely used transformations employing oxime starting materials. We show an enhanced one-pot protocol for photocatalyzed oxime isomerization and subsequent Beckmann rearrangement that enables novel reactivity with alkyl groups migrating preferentially over aryl groups, reversing the regioselectivity of the traditional Beckmann reaction. Chemodivergent N- or O- cyclizations of alkenyl oximes are also demonstrated, leading to nitrones or cyclic oxime ethers, respectively.

Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions

In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.

Preparation method of amide

The invention relates to a preparation method of an amide, wherein, under the action of oxygen, the isothiocyanate and the aldehyde can react to form an amide, and the reaction temperature can be effectively increased only when not less than 110 °C. This process is also suitable for the reaction of isocyanates with aldehydes to produce amides. The preparation method is cheap in raw material, wide in substrate application range and free of metal catalysts in the reaction process. The initiator or other activator is green and economical, and can effectively reduce the cost.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.