615-39-4

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 95-48-7 ortho-cresol 
• 50539-18-9 (+/-)-cis-2-methylcyclohexanol acetate 
• 181962-57-2 Octanoic acid (1R,2S)-2-methyl-cyclohexyl ester 
• 7443-70-1 cis-2-methylcyclohexanol 
• 958447-50-2 ((1R,2R)-2-hydroxycyclohexyl)methyl 2,4,6-trimethylbenzenesulfonate 
• 82166-21-0 methyl cyclohexane 
• 1373216-32-0 tris(4-isopropylphenyl)silyl chloride 
• 22554-27-4 (S)-2-methylcyclohexanone 
• 583-59-5 2-Methylcyclohexanol 
• 591-49-1 1-methylcyclohex-1-ene 
• 99299-20-4 (2R,4R)-2,4,7-trimethyl-1,5-dioxaspiro[5.5]undecane 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 51606-50-9 (1R,2R)-2-(hydroxymethyl)cyclohexanol 

Downstream Products

• 181962-59-4 Diazo-acetic acid (1R,2S)-2-methyl-cyclohexyl ester 
• 35309-56-9 1-iodo-2-methylcyclohexane 
• 931-09-9 1-chloro-2-methyl-cyclohexane 
• 583-60-8 2-Methylcyclohexanone 
• 2133-66-6 2-(trans-2-methylcyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 931-11-3 (1R,2R)-2-methyl-1-cyclohexylamine 
• 591-49-1 1-methylcyclohex-1-ene 
• 111-71-7 heptanal 

Relevant academic research and scientific papers

Catalytic carbonyl hydrosilylations: Via a titanocene borohydride-PMHS reagent system

Reduction of a wide range of aldehydes and ketones with catalytic amounts of titanocene borohydride in concert with a stoichiometric poly(methylhydrosiloxane) (PMHS) reductant is reported. Preliminary mechanistic studies demonstrate that the reaction is mediated by a reactive titanocene(iii) complex, whose oxidation state remains constant throughout the reaction.

Diastereoselective and Enantioselective Silylation of 2-Arylcyclohexanols

The silylation-based kinetic resolution of trans 2-arylcyclohexanols was accomplished by employing a triaryl silyl chloride as the derivatizing reagent with a commercially available isothiourea catalyst. The methodology is selective for the trans diastereomer over the cis, which provides an opportunity to selectively derivatize one stereoisomer out of a mixture of four. By employing this technology, a facile, convenient method to form a highly enantiomerically enriched silylated alcohol was accomplished through a one-pot reduction-silylation sequence that started with a 2-aryl-substituted ketone.

P-Tolylimido rhenium(v) complexes with phenolate-based ligands: Synthesis, X-ray studies and catalytic activity in oxidation with tert-butylhydroperoxide

The reactions of mer-[Re(p-NTol)X3(PPh3)2] (X = Cl, Br) with chelating phenolate-based ligands (2-(2-hydroxy-5-methylphenyl)benzotriazole (HL1), 2-(2-hydroxyphenyl)benzothiazole (HL2) or 2-(2-hydroxyphenyl)benzoxazole (HL3)) afforded a series of p-tolylimido rhenium(v) complexes cis- or trans-(X,X)-[Re(p-NTol)X2(L)(PPh3)]·yMeCN (where X = Cl, Br; L = L1, L2, L3 and y = 0-2) and [Re(p-NTol)X(L)(PPh3)2]Z·pPPh3 (where X = Cl, Br; Z = ReO4, PF6; L = L1, L2, L3 and p = 0 or 1). The reported compounds were characterized by elemental analysis, FT-IR, NMR (1H, 13C and 31P) and X-ray crystallography. Interestingly, the halide ions of [Re(p-NTol)Cl2(L1)(PPh3)]·MeCN (1) and [Re(p-NTol)Cl2(L2)(PPh3)]·2MeCN (3) are in cis relative dispositions, whereas the complexes [Re(p-NTol)Br2(L)(PPh3)] (L1 for 2, L2 for 4 and L3 for 6) and [Re(p-NTol)Cl2(L3)(PPh3)] (5) were found to be trans-(X,X) isomers. The compounds [Re(p-NTol)X(L)(PPh3)2](PF6) (X = Cl, Br; L = L1 and L2) and [Re(p-NTol)X(L3)(PPh3)2](PF6)·PPh3 (X = Cl, Br) have been tested in oxidative catalysis. A few compounds exhibited very good catalytic properties in oxidation of alcohols with tert-BuOOH (TBHP) in acetonitrile solution at moderate temperatures. Complex [Re(p-NTol)Cl(L2)(PPh3)2]PF6 (13) is the catalyst of choice for oxidation of 1-phenylethanol to acetophenone (in 80% yield; turnover number attained 290 after 30 h) and cyclooctanol to cyclooctanone (in 88% yield). Notably lower activity has been found in the oxidation of alkanes with TBHP. Product distribution in the oxidation of methylcyclohexane indicates some steric hindrance around the reaction center.

Cytochrome P450 catalyzed oxidative hydroxylation of achiral organic compounds with simultaneous creation of two chirality centers in a single C-H activation step

Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the respective enantiomeric or diastereomeric alcohols. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild type or mutant forms of the monooxygenase cytochrome P450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives.

New p-tolylimido rhenium(v) complexes with carboxylate-based ligands: Synthesis, structures and their catalytic potential in oxidations with peroxides

Novel p-tolylimido rhenium(v) complexes trans-(Cl,Cl)-[Re(p-NC 6H4CH3)Cl2(pyz-2-COO)(PPh 3)]·MeCN (1), trans-(Cl,Cl)-[Re(p-NC6H 4CH3)Cl2(pyz-2-COO)(PPh

CYCLIC AMINE-1-CARBOXYLIC ACID ESTER DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

Provided is a compound useful as a therapeutic drug for pain and inflammation caused by various pathological conditions such as neuropathic pain and rheumatoid arthritis. The compound of the formula (I) or a salt thereof [wherein R1 is a methyl group or a hydrogen atom, R2 represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an aryl carbonyl group, A represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group (each group may be substituted with a substituent selected from the group consisting of alkyl, alkenyl, cycloalkyl and halogen), n and m each represent an integer of 1, 2 or 3, and p represents an integer of 0, 1, 2 or 3].

CYCLIC AMINE-1-CARBOXYLIC ACID ESTER DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

Provided is a compound useful as a therapeutic drug for pain and inflammation caused by various pathological conditions such as neuropathic pain and rheumatoid arthritis. The compound of the formula (I) or a salt thereof [wherein R1 is a methyl group or a hydrogen atom, R2 represents a hydrogen atom, an alkyl group, an alkylcarbonyl group or an aryl carbonyl group, A represents a cycloalkyl group, a cycloalkenyl group, an aryl group or a heteroaryl group (each group may be substituted with a substituent selected from the group consisting of alkyl, alkenyl, cycloalkyl and halogen), n and m each represent an integer of 1, 2 or 3, and p represents an integer of 0, 1, 2 or 3].

Reductions of cyclic β-keto esters by individual Saccharomyces cerevisiae dehydrogenases and a chemo-enzymatic route to (1R,2S)-2-methyl-1-cyclohexanol

Twenty purified dehydrogenases cloned from bakers' yeast (Saccharomyces cerevisiae) and expressed as fusion proteins with glutathione (S)-transferase were tested for their ability to reduce three homologous cyclic β-keto esters. The majority of dehydrogenases reduced ethyl 2-oxo-cyclopentanecarboxylate, yielding a pair of diastereomeric alcohols with consistent (1R)-stereochemistry. Ethyl 2-oxo-cyclohexanecarboxylate reductions afforded only cis-alcohol enantiomers. Ethyl 2-oxo-cycloheptanecarboxylate was accepted by two enzymes in the collection, and both yielded mainly the cis-(1R,2S)-alcohol. Escherichia coli cells overexpressing the YDL124w gene were used in a dynamic kinetic resolution of ethyl 2-oxo-cyclohexanecarboxylate to produce the key intermediate in a chemo-enzymatic synthesis of (1R,2S)-2-methyl-1-cyclohexanol, an important chiral building block.

Plants-mediated reduction in the synthesis of homochiral secondary alcohols

The reduction of 5-hexen-2-one 1, 6-methyl-5-hepten-2-one 2, acetophenone 3, cis-bicyclo[3.2.0]hept-2-en-6-one 4 and 2-methylcyclohexanone 5 with various commercially available plants (i.e., Brassica oleracea botrytis, Cucurbita maxima, Cucurbita pepo, Cynara scolimus, Daucus carota, Foeniculum vulgare and Musa sapientum) is reported. In the reduction of ketones 1-3, both (S)- and (R)-enantiomers 6-8 were obtained in good yields and with appreciable enantiomeric excesses. With racemic ketones 4 and 5, both the diastereomeric endo/exo 9 and 10 and cis/trans 11 and 12 are produced with variable yields and enantiomeric excesses depending on the various plants used.

Synthesis of chiral building blocks for use in drug discovery

In the past decade there has been a significant growth in the sales of pharmaceutical drugs worldwide, but more importantly there has been a dramatic growth in the sales of single enantiomer drugs. The pharmaceutical industry has a rising demand for chiral intermediates and research reagents because of the continuing imperative to improve drug efficacy. This in turn impacts on researchers involved in preclinical discovery work. Besides traditional chiral pool and resolution of racemates as sources of chiral building blocks, many new synthetic methods including a great variety of catalytic reactions have been developed which facilitate the production of complex chiral drug candidates for clinical trials. The most ambitious technique is to synthesise homochiral compounds from non-chiral starting materials using chiral metal catalysts and related chemistry. Examples of the synthesis of chiral building blocks from achiral materials utilizing asymmetric hydrogenation and asymmetric epoxidation are presented.