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 
• 57-11-4 stearic acid 
• 60718-45-8 1-cyclohexanecarbonyl-1H-imidazole 
• 538-75-0 dicyclohexyl-carbodiimide 
• 3743-70-2 N-(2-hydroxyphenyl)benzamide 
• 18202-04-5 2-Diazacycloheptan-1-one 

Downstream Products

• 101090-33-9 2-cyclohexyLiDene-3-phenyl-oxazolidine-4,5-dione 
• 4664-67-9 <1-Chlor-cyclohexyl>-<4-dimethylamino-phenyl>-keton 
• 6064-01-3 Cyclohexanecarbonyl-phenyl-carbamic acid isopropyl ester 
• 1262796-62-2 C₂₃H₂₃NO 
• 1360571-16-9 2,4-dichlorophenyl N-phenylcyclohexanecarboximidate 
• 91790-88-4 C₁₉H₂₂N₂ 
• 53300-46-2 N-(cyclohexylthiocarbonyl)aniline 
• 128815-38-3 N,N-diphenylcyclohexanecarboxamide 
• 79952-92-4 N-(cyclohexylmethyl)aniline 
• 315712-37-9 N-(4-bromophenyl)-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.

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.

Photoinduced Carbamoylation of C(sp3)H Bonds with Isocyanates

Alkylbenzenes coupled with isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic CH bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex. The present reaction offers a straightforward and atom-economical method for the synthesis of carboxamides starting from hydrocarbons with one-carbon extension.

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Fe-mediated synthesis of: N -aryl amides from nitroarenes and acyl chlorides

Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of N-aryl amides. Starting from commercially available nitroarenes and acyl halides, N-aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.

Chromium-catalyzed ligand-free amidation of esters with anilines

Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.

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.