18349-20-7

Upstream product

• 589-92-4 1-methylcyclohexan-4-one 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 

Downstream Products

• 589-92-4 1-methylcyclohexan-4-one 
• 873312-16-4 4-methyl-2-trifluoroacetyl-1-methoxycyclohexene 
• 27470-41-3 4-methylcyclohexane-1,1-diyl dihydroperoxide 
• 105644-24-4 1,1-Dibromo-4-methyl-cyclohexane 
• 31053-84-6 1-bromo-4-methyl-1-cyclohexene 

Relevant academic research and scientific papers

Synthesis of tetrahydro-2(1H)quinazolinones, cyclopenta[d]-2(1H) pyrimidinones, and their thioxo analogs from 2-trifluoroacetyl-1- methoxycycloalkenes

A series of six (8)-alkyl-4-trifluoromethyl-5,6,7,8-tetrahydro-2(1 H)quinazolinones, 4-trifluoromethyl-cyclopenta[d]-2(1 H)pyrimidinones, and their thioxo analogs from the reaction of five β-alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan-2-ol as solvent and boron trifluoride diethyl etherate as catalyst in 18-65% yield. Copyright Taylor & Francis, Inc.

Synthesis, 17O NMR spectroscopy and structure of 2-trifluoroacetyl-1-methoxycycloalkenes

Among the synthesis of a series of five well-known 2-trifluoroacetyl-1- methoxycycloalkenes derived from cyclopentanone and substituted cyclohexanones, this paper describes the synthesis of three new 2-trifluoroacetyl-1- methoxycycloalkenes derived from cycloheptanone, cyclooctanone and cyclododecanone in 60-68% yield. Subsequently, the 17O NMR chemical shift analysis of the carbonyl and the methoxy groups for these cyclic molecules clearly showed the electron push-pull phenomenon and revealed large and irregular variations of 17O NMR chemical shifts with the ring size. Finally, a more stable conformation of these trifluoroacetyl-containing cycloalkenes was determined by energy minimization calculations using Austin Model 1 (AM1) semi-empirical method and correlations between 17O NMR data and torsion angles or oxygen net charge calculated by AM1 semi-empirical method were performed.

A remarkable bismuth nitrate-catalyzed protection of carbonyl compounds

Bismuth nitrate has been found to be an outstanding catalyst for the protection of carbonyl compounds as acetal, ketal, mixed ketal and thioketal with an excellent yield.

Synthesis of a new water-soluble C2-symmetric chiral diamine: Preliminary investigation of its catalytic properties for asymmetric hydrogenation under biphasic conditions

A water-soluble version of N,N′-dimethyl-1,2-diphenylethane-1,2-diamine was prepared by introduction of phosphonic acid moieties on the para position of the aromatic rings. Preliminary investigation of the catalytic properties of the iridium complex of this ligand under biphasic conditions showed that this system compared well with the homogeneous counterpart for the asymmetric hydrogenation of ketones but with noticeably higher reaction rates for the biphasic system.

Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride. Facile synthesis of β-keto enol ethers

The use of TiCl4, as a catalyst for the acetalisation, at room temperature, of carbonyl compounds is reported. Cyclic ketones and cyclic 1,4-diketones easily afford dimethyl acetals, but cyclic 1,3-diketones give β-keto enol ethers. Additionally, aryl ketones and acyclic ketones failed to react. β-keto aldehydes can be monoprotected either as β-keto enol ethers or β-keto dimethyl acetals depending on the reaction time and catalyst amount. Some mechanistic features are accounted for.

Novel self-coupling reaction of cyclic ketones under a high-pressure mercury lamp

A novel self-coupling reaction in alcohol or hexane-water of cycloalkanone (cycloheptanone, cyclooctanone, and cyclododecanone) with irradiation under a high-pressure mercury lamp yielded the corresponding pinacol-type compound in good yields. In the case of cyclohexanone, 2-methyl-, 2-phenyl-, 4-methylcyclohexanone, 5α- and 5β-cholestan-3-one, the pinacol derivatives were not obtained and the dimethyl acetals were given.

Ce(3+)-Exchanged Montmorillonite (Ce(3+)-Mont) as a Useful Substrate-Selective Acetalization Catalyst

The acetalization of carbonyl compounds with methanol was investigated in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Ce(3+), Zr(4+), Fe(3+), Al(3+), Zn(2+), H(+) and Na(1+).Ce(3+)-mont was found to be the most effective catalyst for substrate-selective acetalization.Cyclohexanones, benzaldehydes, and acid-sensitive 2-furancarboxaldehyde were converted nearly quantitatively to the corresponding acetals in methanol at 25 deg C in the presence of Ce(3+)-mont.The substrates were activated by a Lewis acidic Ce(3+) cation in the interlayer space on the order of 1 kJ mol-1 as measured by FT-IR.The turnover number was estimated to be up to 2.6E3 based on the number of active acid sites in Ce(3+)-mont.

Halogenative Deoxygenation of Ketones; Vinyl Bromides and/or gem-Dibromides by Cleavage of 1,3-Benzodioxoles (Ketone Phenylene Acetals) with Boron Tribromide

Representative ketones 1 have been converted in generally good yields to the respective 1,3-benzodioxoles 5 by trans-acetalization of ketone dimethyl acetals with 1,2-dihydroxybenzene, and cleaved with boron tribromide. 1,3-Benzodioxoles derived from α-unbranched aliphatic ketones gave in general a mixture of vinyl bromides and gem-dibromides; pure gem-dibromides could be selectively obtained in most of cases using a suitable reaction time. 1,3-Benzodioxoles derived from α-branched ketones gave complex mixtures and their cleavage appears to be of little synthetic signifance. 1,3-Benzodioxoles of aromatic ketones gave vinyl bromides only.Aliphatic cyclic gem-dibromides 3 were converted to the respective vinyl bromides 2 by phase-transfer-catalysed dehydrobromination.