2549-58-8

Upstream product

• 591-23-1 m-methylcyclohexanol 
• 25258-92-8 (+/-)-2-methylhexane-1,6-diol 
• 591-24-2 3-Methylcyclohexanone 

Downstream Products

• 855753-60-5 methyl 3-methylcyclohexylacetate 

Relevant academic research and scientific papers

Hydrotalcites as catalysts for the Baeyer-Villiger oxidation of?cyclic ketones with hydrogen peroxide/benzonitrile

Hydrotalcites (HTs) in variable Mg/Al ratios were used as catalysts for the Baeyer-Villiger (BV) oxidation of cyclic ketones with hydrogen peroxide. All HTs studied were found to be active in the BV oxidation of cyclohexanone, their activity increases with increasing Mg/Al ratio. The reaction, which was conducted under very mild conditions (viz. atmospheric pressure and a temperature of 70 °C), provided conversions above 70% with 100% selectivity only after 6 h. This outcome was found to require the presence of a nitrile in the reaction medium, so a mechanism involving adsorption of the nitrile and cyclohexanone onto the catalyst is proposed that is consistent with the experimental results. Based on the proposed mechanism, the presence of a surfactant should result in improved conversion and catalytic activity, as was indeed observed with sodium dodecylsulfate in the reaction medium. The best catalyst among those tested was used with other cyclic ketones and found to provide excellent conversion and selectivity results in most cases.

Optimizing fermentation conditions of recombinant Escherichia coli expressing cyclopentanone monooxygenase

Microbial Baeyer-Villiger oxidation of different substrates with cyclopentanone monooxygenase (CPMO) from Comamonas NCIMB 9872 was up-scaled to benchtop fermenter scale. Conditions for cell growth and biocatalyst production were optimized, and a convenient, environmentally friendly and applicable methodology for the preparation of chiral building blocks for natural product and bioactive compound synthesis was developed by applying a resin based on the concept of in situ "substrate feeding-product removal" (SFPR). Three different ketones (4-methylcyclohexanone, rac-3-methylcyclohexanone, and 8-oxabicyclo[3.2.1]oct-6-en-3-one) were converted in 5-15 g/L scale in a conventional bioreactor, with a volumetric productivity of up to 1 g L -1 h-1 in good to excellent yield and enantiomeric purity.

Baeyer-Villiger oxidation of cyclic ketones using Fe containing MCM-48 cubic mesoporous materials

Iron containing cubic mesoporous MCM-48 materials were prepared by a modified St?ber synthesis method. These materials were characterized by powder X-ray diffraction (XRD), nitrogen isotherms, diffuse-reflectance UV-Vis spectroscopy, and electron microscopy. These materials exhibited high catalytic activity towards the Baeyer-Villiger oxidation of cyclic ketones using benzaldehyde and molecular oxygen. The Fe-MCM-48 mesoporous materials showed excellent recyclability and the integrity of the cubic phase was preserved after the catalytic activity.

Lipase-catalyzed kinetic resolution of racemic seven-membered substituted lactones

Optically active 3-, 4-, 5-, or 6-methyl substituted seven-membered lactones were prepared by Candida antarctica lipase (CAL)-catalyzed kinetic resolution of the racemic lactones. Among these lactones, only in the case of 5-methylhexanolide (R)-isomer reacts faster than the other enantiomer, while the rest of lactones show (S)-selectivity. (C) 2000 Elsevier Science Ltd.

SYNTHESIS OF ALIPHATIC ALCOHOLS AS AROMA CHEMICALS

The present invention relates to a method for preparing a compound of formula (I). The present invention also relates to compounds of formula (A) or a compound in the form of a stereoisomer. The present invention further relates to the use of a compound of formula (A) as aroma chemical.

Stabilized Fe3O4 magnetic nanoparticles into nanopores of modified montmorillonite clay: A highly efficient catalyst for the Baeyer-Villiger oxidation under solvent free conditions

In situ generation of Fe3O4 magnetic nanoparticles (Fe3O4@AT-mont.) into the nanopores of modified montmorillonite (AT-mont.) clay has been carried out. Modification of the montmorillonite was done by acid (4 M HCl) activation under controlled conditions for generating nanopores, which act as a "host" for the Fe3O4 nanoparticles. The synthesized Fe3O4@AT-mont. was characterized by PXRD, TEM, SEM-EDX, XPS, VSM and surface area analysis. The average particle size of Fe3O4 nanoparticles was found to be around 10 nm and exhibit a face centered cubic (fcc) lattice geometry. Fe3O4@AT-mont. showed efficient catalytic activity for the Baeyer-Villiger oxidation of various cyclic and aromatic ketones in the presence of hydrogen peroxide as an oxidant at room temperature under solvent free conditions and exhibited conversion of up to 98%. The catalyst was magnetically recovered and recycled up to the third run without any significant loss of efficiency.

Copper Tetrasulfophthalocyanine Intercalated Hydrotalcite as an Efficient Bifunctional Catalyst for the Baeyer–Villiger Oxidation

Abstract: A heterogeneous bifunctional hybrid catalyst originated from copper tetrasulfophthalocyanine (CuPcTs) and hydrotalcite for Baeyer–Villiger (B-V) oxidation has been prepared and characterized. XRD, FTIR, DR UV-Vis and SEM characterization indicate that CuPcTs molecule has been successfully intercalated into the layer of ZnAl hydrotalcite. And the synthesized hybrid exhibited excellent catalytic activity in the B-V oxidation for various ketones under mild conditions. Its bifunctional role in the reaction through O2/benzaldehyde has been discussed and verified by controlled experiments. The study indicates that the designed catalyst not only catalyzes the oxidation of benzaldehyde to perbenzoic acid, but also accelerates the transformation of ketone to lactone or ester. Graphical Abstract: [Figure not available: see fulltext.]

Oxoiron(iv)-mediated Baeyer-Villiger oxidation of cyclohexanones generated by dioxygen with co-oxidation of aldehydes

In this communication we describe detailed mechanistic studies on the [FeII(CH3CN)(N4Py)(ClO4)]ClO4-catalyzed (N4Py = N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methyl-amine) Baeyer-Villiger oxidation of cyclohexanones by dioxygen with cooxidation of various aldehydes, including the kinetics of the formation and the reactivity of the trapped and spectroscopically characterized oxoiron(iv) intermediate.

New strategies for the synthesis of lactones using peroxymonosulphate salts, ionic liquids and microwave or ultrasound irradiation

A new method for the rapid synthesis of lactones via the one-pot oxidation of alcohols with potassium peroxymonosulphate in an ionic liquid was developed. The use of microwave or ultrasonic irradiation increased the reaction rates significantly. Additionally, new peroxymonosulphate ionic liquids were synthesised and used as effective oxidants in the synthesis of lactones. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014.

Functional divergence between closely related Baeyer-Villiger monooxygenases from Aspergillus flavus

Baeyer-Villiger monooxygenases (BVMOs) catalyse the chemo-, regio- and enantioselective oxidation of ketones to esters and lactones. To date, most of the cloned BVMOs available are derived from bacteria, although Baeyer-Villiger oxidations using fungi have frequently been demonstrated. Here we report the cloning and characterization of four BVMOs from the fungus Aspergillus flavus NRRL3357. Phylogenetic analysis shows these four BVMOs to cluster in a distinct group apart from other well-characterized BVMOs including cyclohexanone, phenylacetone and 4-hydroxyacetophenone monooxygenase. Building on the Grogan classification/clustering of BVMOs, we have designated this new group of BVMOs, Group VI. Group VI BVMOs show an early divergence from the cyclopentanone monooxygenase (CPMO) type BVMOs (Group I). Substrate profiling using cyclic, bicyclic, aliphatic and aryl ketones show a clear divergence in function and specificity not only between this new group of BVMOs and the CPMO-type BVMOs, but also between the four A. flavus BVMO paralogues despite their high sequence similarity. This study not only contributes to the growing number of available BVMOs, but also addresses the current classification of Type I BVMOs, and the usefulness of phylogenetic clustering and prediction of function and selectivity when genome-mining is used to search for new biocatalysts.