6425-41-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2897, 1971 DOI: 10.1021/ja00741a013

InChI:InChI=1/C10H19NO/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h10H,1-9H2

Upstream product

• 92-53-5 4-Phenylmorpholine 
• 4500-29-2 N-cyclohexyl-diethanolamine 
• 110-91-8 morpholine 
• 177-12-8 1,2,4-Trioxaspiro<4.5>decan 
• 108-94-1 cyclohexanone 
• 1192-37-6 methylenecyclohexane 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 108-93-0 cyclohexanol 
• 108-91-8 cyclohexylamine 
• 108-85-0 1-bromocyclohexane 
• 90-05-1 2-methoxy-phenol 
• 150-76-5 4-methoxy-phenol 
• 18979-72-1 3-n-butoxyphenol 
• 150-19-6 O-methylresorcine 

Downstream Products

• 77850-94-3 7-oxo-tetracosanoic acid 
• 91638-51-6 2-[N,N'-bis(ethoxycarbonyl)hydrazino]-1-cyclohexanone 
• 22346-88-9 2,6-bis[N,N'-bis(ethoxycarbonyl)hydrazino]-1-cyclohexanone 
• 698-42-0 tetramethylene-1,3-dithiole-2-thione 
• 117240-07-0 2(3(4'-chlorophenyl)propionyl)cyclohexanone 
• 890005-22-8 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole 
• 6076-13-7 4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid 
• 698-41-9 cyclohexano-1,3-dithiole-2-one 

Relevant academic research and scientific papers

Unusual 1,1-Hydroboration Route to a Reactive Unsaturated Vicinal Frustrated Phosphane/Borane Lewis Pair

Piers' borane HB(C6F5)2 reacted with the alkyne Mes2P-C≡ ≡C-SiMe3 by a rarely observed 1,1-hydroboration reaction under kinetic control to give the unsaturated vicinal frustrated phosphane/borane Lewis pair 6, featuring both the PMes2 and SiMe3 groups at the same carbon atom C1. Compound 6 is a reactive P/B FLP which splits dihydrogen under mild conditions. Thermolysis at 100 °C converts it to the markedly less reactive P/B FLP regioisomer which bears the -SiMe3 substituent at carbon atom C2 adjacent to the B(C6F5)2 group. Most new compounds were characterized by X-ray diffraction.

Production of alkoxyl-functionalized cyclohexylamines from lignin-derived guaiacols

The transformation of renewable lignin-based platform chemicals into value-added nitrogen-containing compounds is an emerging strategy for lignin utilization. However, multi-reactive sites on these platform chemicals make it challenging to control the product selectivity, thereby resulting in limited success. In this work, we developed the reductive-coupling of guaiacol, a typical lignin-based platform chemical, with amines and H2 to synthesize methoxy-functionalized cyclohexylamines. It was demonstrated that Pd/C was a very efficient catalyst for this kind of reaction, and high yields of the target products can be obtained. Notably, this methodology can be applied for the reductive-coupling of various guaiacol analogues with amines to synthesize alkoxyl-functionalized cyclohexylamines with high yields. A mechanism study revealed that the reaction occurred through the generation of 2-methoxycyclohexanone and its subsequent reductive amination. This journal is

Palladium-catalyzed synthesis of 4-cyclohexylmorpholines from reductive coupling of aryl ethers and lignin model compounds with morpholines

This work describes the highly efficient Pd-catalyzed direct coupling of aryl ethers (including the typical lignin model compounds) and morpholines to produce 4-cyclohexylmorpholines, a useful class of fine chemicals. Without employing any acidic additives, various 4-cyclohexylmorpholines could be synthesized with good yields from a variety of aryl ethers using H2 as a hydrogen resource. A mechanism study revealed that the desired product was formed via the cleavage of the C(Ar)-O bonds to generate the corresponding cyclohexanones and subsequent reductive amination. This journal is

RhNPs supported onN-functionalized mesoporous silica: effect on catalyst stabilization and catalytic activity

Amine and nicotinamide groups grafted on ordered mesoporous silica (OMS) were investigated as stabilizers for RhNPs used as catalysts in the hydrogenation of several substrates, including carbonyl and aryl groups. Supported RhNPs on functionalized OMS were prepared by controlled decomposition of an organometallic precursor of rhodium under dihydrogen pressure. The resulting materials were characterized thoroughly by spectroscopic and physical techniques (FTIR, TGA, BET, SEM, TEM, EDX, XPS) to confirm the formation of spherical rhodium nanoparticles with a narrow size distribution supported on the silica surface. The use of nicotinamide functionalized OMS as a support afforded small RhNPs (2.3 ± 0.3 nm), and their size and shape were maintained after the catalyzed acetophenone hydrogenation. In contrast, amine-functionalized OMS formed RhNP aggregates after the catalytic reaction. The supported RhNPs could selectively reduce alkenyl, carbonyl, aryl and heteroaryl groups and were active in the reductive amination of phenol and morpholine, using a low concentration of the precious metal (0.07-0.18 mol%).

Reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3as a reductant

Herein, we report the first example of efficient reductive amination of ketones/aldehydes with amines using BH3N(C2H5)3 as a catalyst and a reductant under mild conditions, affording various tertiary and secondary amines in excellent yields. A mechanistic study indicates that BH3N(C2H5)3 plays a dual function role of promoting imine and iminium formation and serving as a reductant in reductive amination. This journal is

Method for preparing 4-cyclohexylmorpholine compound by using lignin model compound

The invention discloses a method for preparing a 4-cyclohexylmorpholine compound by using a lignin model compound, which is characterized by comprising the following steps: respectively dissolving thelignin model compound and a morpholine ether amine compound in a m-xylene solution, and carrying out coupling reaction in the presence of a Pd/C catalyst in a hydrogen atmosphere to prepare a 4cyclohexyl morpholine derivative and a derivative thereof, wherein the Pd/C catalyst is mixed with a lignin model compound, a morpholine ether amine compound and m-xylene according to a ratio of 1 mmol: 16-34 mmol: 25-50 mmol: 50-100 ml based on Pd, a stirring reaction is performed for 6-12 h at a temperature of 90-150 DEG C, a reaction liquid is cooled to a room temperature, and filtration is performedto prepare the 4-cyclohexyl morpholine compound. Compared with the prior art, the method has the advantages that the raw materials are easy to obtain, the production cost is low, the use of a heavy metal reagent is avoided, and the method is a green, environment-friendly, economical and efficient method for directly and efficiently preparing the 4-cyclohexylmorpholine and the derivative thereof by utilizing the aromatic ether.

Glycerol Boosted Rh-Catalyzed Hydroaminomethylation Reaction: A Mechanistic Insight

We report a Rh-catalyzed hydroaminomethylation reaction of terminal alkenes in glycerol that proceeds efficiently under mild conditions to produce the corresponding amines in relatively high selectivity towards linear amines, moderate to excellent yields by using a low catalyst loading (1 mol % [Rh], 2 mol % phosphine) and relative low pressure (H2/CO, 1:1, total pressure 10 bar). This work sheds light on the importance of glycerol in enabling enamine reduction via hydrogen transfer. Moreover, evidence for the crucial role of Rh as chemoselective catalyst in the condensation step has been obtained for the first time in the frame of the hydroaminomethylation reaction by precluding deleterious aldol condensation reactions. The hydroaminomethylation proceeds under a molecular regime; the outcome of catalytically active species into metal-based nanoparticles renders the catalytic system inactive.

Synthesis of Arylamines via Non-Aerobic Dehydrogenation Using a Palladium/Carbon-Ethylene System

The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and co-product of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds. (Figure presented.).

Colloid and Nanosized Catalysts in Organic Synthesis: XVIII.1 Disproportionation and Cross-Coupling of Amines During Catalysis with Immobilized Nickel Nanoparticles

It has been stated that immobilized nickel nanoparticles catalyze disproportionation and cross-coupling of amines. The influence of the support on the catalysis of these properties in the in plug-flow reactor has been studied. The use of active carbon as the support has been found advantageous for the cross-coupling of amines, whereas alumina was a better support for the disproportionation reaction.

Facile access to: N -substituted anilines via dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles

N-Substituted anilines are widely utilized important compounds, and the development of their diverse synthetic procedures is of great significance. Herein, we have successfully developed a widely applicable powerful catalytic route to N-substituted anilines. In the presence of a gold-palladium alloy nanoparticle catalyst (Au-Pd/Al2O3) and styrene, various kinds of structurally diverse N-substituted anilines (twenty three examples) could be synthesized starting from cyclohexanones and amines (including aliphatic primary and secondary amines and anilines). The catalytic performance was strongly influenced by the nature of the catalyst. A supported gold catalyst (Au/Al2O3) was completely inactive for the present transformation. Although a supported palladium catalyst (Pd/Al2O3) gave the desired N-substituted anilines to some extent, the performance was inferior to that of Au-Pd/Al2O3. The catalytic activity of the palladium species in Au-Pd/Al2O3 was at least ca. three times higher than that in Pd/Al2O3. Moreover, the performance of Au-Pd/Al2O3 was superior to that of a physical mixture of Au/Al2O3 and Pd/Al2O3. Thus, palladium was intrinsically effective for the present transformation (dehydrogenative aromatization) and its performance was improved by alloying with gold. The present transformation proceeds through a sequence of the dehydrative condensation of cyclohexanones and amines to produce enamines (or ketimines), followed by the dehydrogenative aromatization to produce the corresponding N-substituted anilines. In the aromatization step, styrene could act as an effective hydrogen acceptor to selectively produce the desired N-substituted anilines without catalyzing the disproportionation of the enamine intermediates. The observed catalysis using Au-Pd/Al2O3 was truly heterogeneous in nature, and Au-Pd/Al2O3 could be reused.