10264-08-1

Usage

Uses

Used in Pharmaceutical Industry:
N-cyclohexylphenylacetamide is used as a precursor in the synthesis of various drugs, primarily for its role in creating pain relievers and anti-inflammatory medications. Its unique structure allows for the development of compounds that can effectively target and alleviate pain and inflammation.
Used in Agricultural Industry:
In the agricultural sector, N-cyclohexylphenylacetamide is utilized in the manufacturing of insecticides and herbicides. Its chemical properties make it suitable for controlling pests and unwanted plant growth, thereby contributing to more efficient and productive agricultural practices.
The diverse applications of N-cyclohexylphenylacetamide stem from its ability to be integrated into the composition of various chemical products, highlighting its importance across different industries.

InChI:InChI=1/C14H19NO/c16-14(11-12-7-3-1-4-8-12)15-13-9-5-2-6-10-13/h1,3-4,7-8,13H,2,5-6,9-11H2,(H,15,16)

Upstream product

• 14277-11-3 N-cyclohexyl-2-phenyl-acetamidine 
• 542-18-7 cyclohexyl chloride 
• 140-29-4 phenylacetonitrile 
• 108-91-8 cyclohexylamine 
• 101-97-3 Ethyl 2-phenylethanoate 
• 103-80-0 phenylacetyl chloride 
• 937-39-3 2-phenylacetylhydrazine 
• 50743-09-4 Cyclohexylphenylketenimin 
• 65439-58-9 2-phenyl-1-(2-thioxothiazolidin-3-yl)ethan-1-one 
• 5330-97-2 N-hydroxy-2-phenylacetamide 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 3173-53-3 Cyclohexyl isocyanate 
• 51463-66-2 dimethyl (2-phenylacetyl)phosphonate 
• 13504-37-5 diethyl phenylacetylphosphonate 

Downstream Products

• 56714-16-0 3-Cyclohexyl-5,5-diallyl-2-phenylmethylen-tetrahydro-1,3-oxazin-4,6-dion 
• 50743-09-4 Cyclohexylphenylketenimin 
• 74157-85-0 N-cyclohexyl-phenylacetimidoyl chloride 
• 74366-19-1 Cyclohexyl-[3,4,4-triphenyl-thietan-(2Z)-ylidene]-amine 
• 67684-90-6 N-Cyclohexyl-2,3,3-triphenylthioacrylamide 

Relevant academic research and scientific papers

Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide18O-labeling

The mechanism of umpolung amide synthesis was probed by interrogating potential sources for the oxygen of the product amide carbonyl that emanates from the α-bromo nitroalkane substrate. Using a series of 18O-labeled substrates and reagents, evidence is gathered to advance two pathways from the putative tetrahedral intermediate. Under anaerobic conditions, a nitro-nitrite isomerization delivers the amide oxygen from nitro oxygen. The same homolytic nitro-carbon fragmentation can be diverted by capture of the carbon radical intermediate with oxygen gas (O2) to deliver the amide oxygen from O2. This understanding was used to develop a straightforward protocol for the preparation of 18O-labeled amides in peptides by simply performing the umpolung amide synthesis reaction under an atmosphere of 18O2.

Preparation of polymer-bound pyrazolone active esters for combinatorial chemistry

The preparation of solid-phase active esters from a new pyrazolone linker resin is described. N-Acylation using this resin provides various amide products with a high conversion rate and good purity under mild conditions. The polymer-bound pyrazolone linkers are stable in the reaction conditions and are resistant to hydrolysis. Moreover, this resin can also be reused repeatedly without a loss of reactivity.

Reactions of acyl nitroso compounds with amines: Production of nitroxyl (HNO) with the preparation of amides

Oxidation of hydroxamic acids in the presence of amines generates nitrous oxide (N2O) and the corresponding amide. The identification of N2O suggests the intermediacy of nitroxyl (HNO). Retro-Diels Alder dissociation of cyclopentadiene-acyl nitroso compound cycloadducts releases N2O with amide formation.

Amino-functionalized carbon nanotubes as nucleophilic scavengers in solution phase combinatorial synthesis

A versatile method for fast scavenging a variety of electrophiles using carbon nanotubes functionalized by amino groups (CNT-NH2) is reported. Following the scavenging event, CNT-NH2 can be easily separated from the reaction mixture by filtration, leaving the desired products in excellent yields and purities.

Sulfated tungstate: A new solid heterogeneous catalyst for amide synthesis

Amide formation avoiding poor atom economy reagents is a priority area. We have synthesized sulfated tungstate as a new reusable and environmentally benign heterogeneous catalyst for direct amide formation between carboxylic acid and amine. It has potential for large scale applications.

Synthesis of some α-ketophosphonates comprising mobile hydrogens in position α: Spectroscopic characteristics of 1H, 13C, 31P NMR and IR reactivities among amines and hydrazine derivatives

In the present work we describe the keto-enol equilibrium of some acylphosphonates 1 by means of 1H, 13C, 31P NMR, and IR data which show that the enol form has E configuration. The keto/enol ratio is determined on the basis of 31P NMR data. The reactivity of 1 with hydrazines derivatives and primary amines are reported. The structure of all compounds is determined by 1H, 13C, 31P NMR, and IR.

Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium

A new method for oxidative synthesis of amides from alkynes and amines in high yields (up to 96%) using [Mn(2,6-Cl2TPP)Cl] 1 as a catalyst and Oxone/H2O2 as an oxidant in aqueous medium has been developed. This method could be used for N-terminal α-amino group ligation of unprotected peptides with aryl, aliphatic, and internal alkynes under mild conditions. Copyright

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.

Metal-free Photocatalytic Intermolecular anti-Markovnikov Hydroamination of Unactivated Alkenes

The development of photocatalytic intermolecular hydroamination reaction between N-aminated dihydropyridines and unactivated alkenes is reported. Metal-free co-catalysts, rhodamine 6G and thiophenol, in presence of visible light are used to initiate the process. The transformation shows a broad substrate scope, both alkenes and amidyl radical can act as coupling partners. The radical strategy provides excellent anti-Markovnikov selectivity and regioselectivity in diene substrates.

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.