58008-17-6

Basic information

• Product Name: Benzenamine, N-(1-cyclohexylethyl)-
• CAS NO: 58008-17-6
• Molecular Formula: C14H21N
• Molecular Weight: 203.327
• Mol File: 58008-17-6.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-(1-cyclohexylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-(1-cyclohexylethyl)-(58008-17-6)
• EPA Substance Registry System: Benzenamine, N-(1-cyclohexylethyl)-(58008-17-6)

Safety Data

• Hazardous Substances Data: 58008-17-6(Hazardous Substances Data)

Upstream product

• 476148-85-3 N-phenyl-[1-(cyclohexyl)ethylidene]amine 
• 56037-35-5 [1-Cyclohexyl-eth-(E)-ylidene]-phenyl-amine 
• 823-76-7 Cyclohexyl methyl ketone 
• 62-53-3 aniline 

Relevant articles and documents

Revisiting the Stereodetermining Step in Enantioselective Iridium-Catalyzed Imine Hydrogenation

The mechanism for the iridium-catalyzed asymmetric hydrogenation of prochiral imines has been investigated for an experimentally relevant ligand-substrate combination using DFT calculations. The possible stereoisomers of the stereodetermining hydride tran

Chiral Br?nsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane

The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Br?nsted acid catalyst is reported. This is the first known example of chiral Br?nsted acid-catalyzed asymmetric reductive amination using

Zirconium complexes stabilized by amine-bridged bis(phenolato) ligands as precatalysts for intermolecular hydroamination reactions

A series of zirconium complexes bearing amine-bridged bis(phenolato) ligands of different steric and electronic properties have been synthesized, and their activities in catalyzing intermolecular hydroamination reactions have been studied and compared. In

Synthesis of group 4 metal complexes stabilized by an amine-bridged bis(phenolato) ligand and their catalytic behavior in intermolecular hydroamination reactions

Zirconium and titanium complexes 1 and 2, bearing an amine-bridged bis(phenolato) ligand, have been synthesized and characterized. Although 1 and 2 were inactive in catalyzing intermolecular hydroamination reactions, cationic complexes generated in situ f

L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: Effects of the side amide group on catalytic performances

A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure-efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines. The Royal Society of Chemistry 2013.

Triazole-Au(I) complexes: A new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination

(Chemical Equation Presented) A series of 1,2,3-triazole-bound cationic Au(I) catalysts have been synthesized, and their structures have been characterized by X-ray crystallography. Variable-temperature NMR studies revealed dynamic triazole-Au cation coor

Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile

l-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the

[Zinc-diamine]-catalyzed hydrosilylation of ketones in methanol. New developments and mechanistic insights

The Zn-promoted direct reduction of various ketones, including alkyl aryl ketones, α- and β-keto esters, α- and β-keto amides, into the corresponding alcohols with polymethylhydrosiloxane (PMHS) in protic conditions is reported. The reaction proceeds chemoselectively under smooth conditions, with simple catalyst combinations based on a zinc precursor [ZnEt2, Zn(OMe)2, Zn(OH)2] and a 1,2-diamine ligand, e.g., N,N′-dibenzylethylenediamine (dbea). The reaction rates are significantly faster than under aprotic conditions. For β-keto esters and amides, the use of an excess of PMHS is required. Moderate enantioselectivities (ee up to 55%) have been obtained using a variety of enantiopure diamine ligands. Two mechanisms are proposed for the new catalytic reaction, on the basis of the synthesis of [(diamine)Zn(alkoxide)2] complexes which are models of the possible reaction intermediates and a study of their activity.

Direct Zn-diamine promoted reduction of C=O and C=N bonds by polymethylhydrosiloxane in methanol

Ketones and imines are chemoselectively reduced at room temperature in methanol to the corresponding alcohols and amines in high yields in a one-step procedure using polymethylhydrosiloxane (PMHS) and a simple zinc-diamine catalyst.

Ruthenium-catalyzed transfer hydrogenation of imines by propan-2-ol in benzene

Transfer hydrogenation of a variety of different imines to the corresponding amines by propan-2-ol in benzene catalyzed by [Ru2(CO)4(μ H)(C4Ph4COHOCC4Ph4)] (1) has been studied. The reaction is highly efficient with turnover frequencies of over 800 per hour, and the product amines were obtained in excellent yields. A remarkable concentration dependence of propan-2-ol was observed when the reaction was run in benzene as cosolvent. An optimum was obtained at 24 equivalents of propan-2-ol to imine, and further increase of the propan-2-ol led to a dramatic decrease in rate. Also the use of polar cosolvents with 24 equivalents of propan-2-ol gave a low rate. It was found that ketimines react faster than aldimines and that electron-donating substituents on the imine increase the rate of the catalytic transfer hydrogenation. Electron-withdrawing substituents decreased the rate. An isomerization was observed with imines having an α-hydrogen at the N-alkyl substituent, which is in accordance with a mechanism involving a ruthenium-amine intermediate. It was demonstrated that the ruthenium-amine complex from α-methylbenzylamine, corresponding to the postulated intermediate, can replace 1 as catalyst in the transfer hydrogenation of imines. A primary deuterium isotope effect of kCH/CD = 2.7 ± 0.25 was observed when 2-deuterio-propan-2-ol vas used in place of propan-2-ol in the ransfer hydrogenation of N-phenyl-(1-phenylethylidene)amine.