13619-73-3

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 64-17-5 ethanol 
• 110-83-8 cyclohexene 
• 930-68-7 cyclohexenone 
• 1801-77-0 oxovanadium(V) ethoxydichloride 

Downstream Products

• 329204-72-0 3-pyridin-2-ylethynyl-cyclohex-2-enol 
• 329204-47-9 3-(pyridin-2-ylethynyl)cyclohex-2-enone 

Relevant academic research and scientific papers

Concentration and solvent effects on the conformational equilibrium of cis-3-ethoxycyclohexanol by 1H NMR and IR spectroscopy

NMR data, in CCl4, show that an increase in the concentration of cis-3-ethoxycyclohexanol (cis-3-ECH) shifts the conformational equilibrium from the ax-ax conformer (Xax-ax=51% at 0.01 mol L-1), stabilized by an intramolec

Direct organocatalytic hydroalkoxylation of α,β-unsaturated ketones

The direct addition of a variety of alcohols to in situ activated olefins was observed in the presence of mild bifunctional amine/acid catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals. The use of simple commercially available catalysts, amines and acids makes this an attractive method for the preparation of β-alkoxy ketones, which are prevalent targets and intermediates in organic synthesis.

Bismuth trichloride-catalyzed oxy-Michael addition of water and alcohol to α,β-unsaturated ketones

An efficient method was developed for the conjugate addition of water to various α,β-unsaturated ketones by using bismuth(III) chloride as a catalyst. The reactions proceeded smoothly in the presence of a catalytic amount of BiCl3 (20 mol%) in aqueous media to furnish a variety of synthetically useful β-hydroxyl ketones in moderate to good yields. Apart from water molecule, various alcohols could also be employed as nucleophiles to react with α,β-unsaturated ketones, leading to β-alkoxyl ketones in modest to high yields. In addition, the mild reaction conditions also entailed the conjugate addition reactions to proceed with the tolerance to a range of functional groups.

Indium(III)-Catalyzed Hydration and Hydroalkoxylation of α,β-Unsaturated Ketones in Aqueous Media

The hydration of α,β-unsaturated ketones with water proceeded efficiently in the presence of In(OTf)3 (20 mol%) in aqueous media to afford synthetically versatile β-hydroxyketones in moderate to good yields with good functional group compatibility. The method also can be extended to the hydroalkoxylation of α,β-unsaturated ketones with various alcohols for the efficient synthesis of β-alkoxyketones as well as tetrahydrofuran derivatives. (Figure presented.).

Chromium(III)-Catalyzed Addition of Water and Alcohol to α,β-Unsaturated Ketones for the Synthesis of β-Hydroxyl and β-Alkoxyl Ketones in Aqueous Media

An efficient chromium(III) chloride-catalyzed Michael-type reaction of water or alcohol with α,β-unsaturated ketones is developed. A variety of α,β-unsaturated ketones effectively reacted with either water or alcohols to give the corresponding β-hydroxyl ketones or β-alkoxyl ketones in modest to high yields with excellent compatibility to various functional groups. The approach was further utilized for the preparation of synthetically useful compounds containing tetrahydrofuran skeleton.

Efficient hydrogenation of ketones catalyzed by an iron pincer complex

Reductions made easy: A highly efficient iron catalyst effects the homogeneous hydrogenation of ketones under very mild conditions (see scheme). A mechanism including the insertion of the ketone into the Fei-H bond, followed by addition of hydrogen to a dearomatized intermediate is proposed.

Catalytic behavior of melamine glyoxal resin towards consecutive oxidation and oxy-Michael addition

Synthesis of melamine glyoxal resin involves a catalyst-free, one pot reaction between melamine and glyoxal in DMF. The synthesized resins have a similar morphological arrangement to that of layered materials as depicted by their XRD pattern and Raman spectra. The catalytic behavior of melamine glyoxal resin (MGR) have been studied in allylic oxidation of cyclohexene and simultaneous Michael addition. The MGR/solvent/O2 oxidant system can be regarded as a metalfree, additive-free, cost-effective and environmentally benign catalytic system. The oxidative behavior of MGR is attributed to its ability to generate in situ organic peroxide species during the course of reaction. Generation of peroxide species is confirmed by the KI/starch test and further confirmed by the complete suppression effect of TEMPO (2,2,6,6- tetramethylpiperidine-1-oxyl) over oxidation. The activity for Michael addition can be attributed to the presence of a higher content of nitrogen atoms, which serves as the active site. In oxidation, 28.1% conversion of cyclohexene with 37.19 and 62.81% selectivities for cyclohexenol and cyclohexenone were observed, respectively. In consecutive oxidation and oxy-Michael addition, 31.5% conversion of cyclohexene was observed with selectivities of 61.6% for cyclohexenone and 38.4% for alkoxy product. Springer Science+Business Media B.V. 2010.

An exceptionally rapid and selective hydrogenation of 2-cyclohexen-1-one in supercritical carbon dioxide

Selective hydrogenation of 2-cyclohexen-1-one over Pt-MCM-41 proceeds at a very high rate and produces cyclohexanone with selectivity of 100% in a batch reactor; a marked increase in the reaction rate (TOF) from 2283 min-1 to 5051 min-1 is observed on increasing the pressure from 7 MPa to 14 MPa at 40°C. The Royal Society of Chemistry 2009.

Application of high pressure induced by water-freezing to the Michael reaction of alcohols with α,β-enones

High pressure (about 200MPa), which was realized by freezing water in a sealed autoclave, has been successfully applied to a high-yield Michael reaction of alcohols and α,β-unsaturated ketones in the presence of a catalytic amount of DMAP and LiClO4. Only a moderate yield was obtained under atmospheric pressure.

Hydrogenation of Vinylogous Esters

Methods for hydrogenation of the vinylogous ester linkage have been investigated.The ideal method appears to be hydrogenation over a palladium on charcoal catalyst, using THF as the solvent.Classical methods such as hydrogenation in hydroxylic solvents an