1759-68-8

Usage

InChI:InChI=1/C13H17NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1,3-4,7-8,12H,2,5-6,9-10H2,(H,14,15)

Upstream product

• 23554-71-4 (E)-cyclohexyl(phenyl)methanone oxime 
• 93-58-3 benzoic acid methyl ester 
• 108-91-8 cyclohexylamine 
• 93-59-4 Perbenzoic acid 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 614-28-8 N-benzoylbenzamide 
• 98-88-4 benzoyl chloride 
• 542-18-7 cyclohexyl chloride 
• 100-47-0 benzonitrile 
• 108-93-0 cyclohexanol 
• 3376-25-8 (Z)-N-benzylidenecyclohexanamine oxide 
• 75-36-5 acetyl chloride 
• 614-45-9 tert-Butyl peroxybenzoate 
• 538-75-0 dicyclohexyl-carbodiimide 

Downstream Products

• 4383-25-9 N-benzylcyclohexylamine 
• 62250-62-8 N-cyclohexyl-N-nitroso-benzamide 
• 31144-23-7 N-cyclohexylbenzimidoyl chloride 
• 827-52-1 1-phenyl-1-cyclohexane 
• 13941-93-0 N-(4-Hydroxy-cyclohexyl)-benzamide 
• 108-94-1 cyclohexanone 
• 108-91-8 cyclohexylamine 
• 65-85-0 benzoic acid 
• 10220-98-1 N-cyclohexyl-thiobenzamide 
• 13942-05-7 N(4-oxo)-Cyclohexylbenzamid 
• 14156-24-2 N-(4-Oxo-cycloheptyl)-benzamide 
• 874571-95-6 N-(azidoacetyl)-N-cyclohexylbenzamide 
• 1401413-04-4 (Z)-N-(1-phenylpentylidene)cyclohexanamine 
• 1401413-03-3 (E)-N-(1-phenylpentylidene)cyclohexanamine 

Relevant academic research and scientific papers

Exploring the coordination chemistry of 1-benzoyl-4,5-dihydro-3,5- bis(trifluoromethyl)-1H-pyrazol-5-ol to copper

The coordination chemistry of the ligand 1-benzoyl-4,5-dihydro-3,5- bis(trifluoromethyl)-1H-pyrazol-5-ol (1a) has been recently investigated. In dependency of the metal (e.g., nickel, zinc, molybdenum) and the added co-ligand (phosphanes, pyridines, amine

CuBr-catalysed oxidative desulfurisation of thiobenzamides

An efficient oxidative desulfurisation of thioamides by CuBr/TBHP is reported. Thioamides containing alkyl or aryl on the nitrogen undergo desulfurisation and give amides with good yields. Thioamides not containing substituent on the nitrogen undergo desulfurisation and give 1,2,4-thiadiazoles in moderate to good yields.

Molecular rearrangement of 1-substituted 3-aminoquinoline-2,4-diones in their reaction with urea and nitrourea synthesis and transformations of reaction intermediates

1-Substituted 3-alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones (6) react with nitrourea to give 3-ureido-1H,3H-quinoline-2,4-diones (10), 9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2,4-diones (11), and 3,3a-dihydro-5H-imidazo[4,5-c]quinoline-2,4-diones (12). Compounds 11 were dehydrated to 12 by the action of phosphorus pentoxide. All three types of compounds rearrange in boiling acetic acid to give three different types of products of molecular rearrangement. A proposed reaction mechanism is discussed.

Gas-phase formation of protonated benzene during collision-induced dissociation of certain protonated mono-substituted aromatic molecules produced in electrospray ionization

Protonated benzene, C6H+7, has been studied extensively to understand the structure and energy of a protonated organic molecule in the gas phase. The formation of C6H+7 is either through direct protonation of benzene, i.e., chemical ionization, or through fragmentation of certain radical cations produced from electron ionization or photon ionization. We report a novel observation of C6H+7 as a product ion formed in the collision-induced dissociation (CID) of protonated benzamide and related molecules produced via electrospray ionization (ESI). The formation of C6H+7 from these even-electron precursor ions during the CID process, which has not been previously reported, is proposed to occur from the protonated molecules via a proton migration in a five-membered ring intermediate followed by the cleavage of the mono-substituent C-C bond and concurrent formation of an ion-molecule complex. This unique mechanism has been scrutinized by examining some deuterated molecules and a series of structurally related model compounds. This finding provides a convenient mean to generate C6H+7, a reactive intermediate of considerable interest, for further physical or chemical investigation. Further studies indicate that the occurrence of C6H+7 in liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) appears to be a rather common phenomenon for many compounds that contain 'benzoyl-type' moieties. Hence, the observation of the C6H+7 ion in LC/ESI-MS/MS can be used as an informative fragmentation pathway which should facilitate the identification of a great number of compounds containing the 'benzoyl-type' and similar structural features. These compounds are frequently present in food and pharmaceutical products as leachable impurities that require strict control and rapid elucidation of their identities.

Facile synthesis of phosphaamidines and phosphaamidinates using nitrilium ions as an imine synthon

Readily accessible nitrilium triflates are convenient imine building blocks for the expedient synthesis of a novel class of 1,3-P,N ligands as demonstrated for the reaction with primary phosphanes. This procedure allows variation of all substituents. X-ray crystal structures are reported for nitrilium ions, phosphaamidines, and three phosphaamidinate complexes. The lithium phosphaamidinate is N coordinated and its reaction with [AuCl(tht)] (tht=tetrahydrothiophene) gives a unique P-bridged gold trimer, while a P,N-bidentate complex results from [{RhCl(cod)}2]. The nitrilium ion methodology allows extension of the 1,3-P,N motive to bis(imino)phosphanes, which are the neutral phosphorus analogues of the valuable β-diketiminate ligand.

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Photocatalysis in Aqueous Micellar Media Enables Divergent C-H Arylation and N-Dealkylation of Benzamides

Photocatalysis in aqueous micellar media has recently opened wide avenues to activate strong carbon-halide bonds. So far, however, it has mainly explored strongly reducing conditions, restricting the available chemical space to radical or anionic reactivity. Here, we demonstrate a controllable, photocatalytic strategy that channels the reaction of chlorinated benzamides via either a radical or a cationic pathway, enabling a chemodivergent C-H arylation or N-dealkylation. The catalytic system operates under mild conditions with methylene blue as a photocatalyst and blue LEDs as the light source. Factors determining the reactivity of substrates, their selectivity, and preliminary mechanistic studies are presented.

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst

A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Method for preparing amide from carboxylic acid under irradiation of blue light by taking iridium and cobalt complexes as catalysts

The invention relates to a method for preparing amide from carboxylic acid under the irradiation of blue light by taking iridium and cobalt complexes as catalysts, and belongs to the field of chemistry. The method comprises the following step of: by taking R substituted carboxylic acid and R1' and R2' substituted amines as raw materials, triphenylphosphine as a deoxidizing agent, [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as a photocatalyst and Co(dmgH)(dmgH2)Cl2 as a metal complex catalyst, reacting in dichloromethane in an inert atmosphere and under the irradiation of blue light to obtain an amide compound, wherein R is an aryl group, a heteroaryl group, a protected amino group, a substituted alkyl group, a substituted aryl group or a substituted protected amino group, R1' is a hydrogen group, a substituted alkyl group, a phenyl group or a substituted phenyl group, and R2' is a hydrogen group, a substituted alkyl group, a phenyl group or a substituted phenyl group.