16179-64-9

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 108-91-8 cyclohexylamine 

Downstream Products

• 16195-95-2 3-(N-cyclohexyl-N-methyl)aminocyclohex-2-enone 
• 78890-82-1 3-(Cyclohexyl-methyl-amino)-6-methyl-cyclohex-2-enone 
• 78890-85-4 3-(Cyclohexyl-methyl-amino)-4-methyl-cyclohex-2-enone 
• 1220516-06-2 3-[cyclohexyl(4-nitrophenyl)amino]-2-iodocyclohex-2-enone 
• 16179-46-7 2-Acetyl-3-cyclohexylamino-cyclohex-2-enone 
• 78890-77-4 5-(Cyclohexyl-methyl-amino)-cyclohexa-1,5-dienol anion 
• 78890-78-5 3-(Cyclohexyl-methyl-amino)-cyclohexa-1,3-dienol anion 

Relevant academic research and scientific papers

Ytterbium triflate catalyzed synthesis of β-enaminones

β-Enaminones have been synthesized in very good yield under solvent-free conditions from differently substituted amines and β-diketones in the presence of Yb(OTf)3 as catalyst. The method is applicable to cyclic and acyclic ketones, aromatic an

Redox Property of Enamines

Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.

Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols

A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis. (Figure presented.).

Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones

A highly efficient hypervalent iodine-promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β-enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The meth

Continuous flow iodination using an automated computer-vision controlled liquid-liquid extraction system

A dynamic computer-vision control system incorporating open-source software technologies (Python, OpenCV) was used to automate a gravity based in-line liquid-liquid extraction during the iodination of enaminones in continuous flow. The system was able to cope with significant colouration of the organic reaction stream and with significant volume/flow changes in the aqueous and organic phase streams due to extraction of the water soluble acetonitrile co-solvent.

Continuous Flow Liquid-Liquid Separation Using a Computer-Vision Control System: The Bromination of Enaminones with N -Bromosuccinimide

Incorporating open-source software components (Python, OpenCV), a computer-vision system was used to control the interface level in a gravity-based inline liquid-liquid separation device. This was used in the continuous flow bromination of a series of enaminone substrates. The main byproduct of the reaction, succinimide, was efficiently extracted into the aqueous stream, providing clean products without the need for further purification.

Concurrent α-iodination and N-arylation of cyclic β-enaminones

A variety of N-substituted 3-aminocyclohex-2-enones were converted into the corresponding N-arylated α-iodo enaminones in high yields via concurrent N-iodination and N-arylation mediated by ArI(OAc)2. A mechanism is postulated to account for the reaction differences between the cyclic and the acyclic -enaminones, which undergo predominant β-acetoxylation under the same reaction conditions.

Selectivity in β-Enamino Ketone Anion Generation and Alkylation

The regioselectivity of anion generation from β-alkoxy- and β-(dialkylamino)-α,β-unsaturated ketones was probed by use of (13)C NMR spectroscopy and alkylation techniques.Results indicate that the kinetic anions of these systems can be formed selectively from the parent ketones by using excess lithium diisopropylamide as the base at -78 deg C and diethyl ether or tetrahydrofuran as the solvent.The kinetic anion in these systems is the one resulting from deprotonation at the α'-carbon.Alkylation occurs at this center in synthetically useful yields.Equilibration to produce the thermodynamically more stable extended γ-enolate anion occurs when less than 1 equiv of lithium diisopropylamide is present and at elevated temperatures (>-20 deg C).The rate of equilibration is sensitive to the solvent employed, occurring much more rapidly in tetrahydrofuran than in diethyl ether.A synthetically more practical method for formation and alkylation of the thermodynamic anions of β-(dialkylamino)-α,β-unsaturated ketones utilizes excess lithium bis(trimethylsilyl)amide as the base in tetrahydrofuran as the solvent at -78 deg C followed by quenching with the alkylating agent.Methods for regioselective generation of dianions from β-(alkylamino)-α,β-unsaturated ketones have been explored.Analysis of products produced by methylation suggest that the N,α'- and N,γ-dianions can be produced independently by use of the respective kinetic and thermodynamic anion-producing conditions described above.However, all attempts to identify these dianions by spectroscopic methods failed due to the exceedingly low solubilities of these substances in solvent systems compatible with the technique.Likewise, dialkylation or acyclation-alkylation of the N,γ-dianions, in attempts to develope one-step procedures for fused-bicyclic pyrrolidine synthesis, was unsuccessful.