3483-39-4

Usage

InChI:InChI=1/C8H14O/c1-2-4-7(5-3-1)8-6-9-8/h7-8H,1-6H2

Upstream product

• 695-12-5 vinylcyclohexane 
• 6051-09-8 2-cyclohexyl-3-hydroxypropanoic acid 
• 130318-72-8 methyldiphenyltelluronium tetraphenylborate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 186581-53-3 diazomethane 
• 74-97-5 chlorobromomethane 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 593-71-5 Chloroiodomethane 
• 75-11-6 diiodomethane 
• 2181-44-4 trimethylsulfonium methylsulfate 
• 2181-42-2 trimethylsulphonium iodide 
• 823-76-7 Cyclohexyl methyl ketone 
• 56077-28-2 Bromomethyl cyclohexyl ketone 
• 1774-47-6 trimethylsulfoxonium iodide 

Downstream Products

• 87050-10-0 (+/-)-1-cyclohexyl-2-pyrrolidinoethanol 
• 127677-24-1 1-cyclohexyl-2-dimethylamino-ethanol 
• 111221-89-7 Toluene-4-sulfonic acid 2-cyclohexyl-2-hydroxy-ethyl ester 
• 111221-90-0 Toluene-4-sulfonic acid 1-cyclohexyl-2-hydroxy-ethyl ester 
• 695-12-5 vinylcyclohexane 
• 1193-81-3 rac-1-cyclohexylethanol 
• 4442-79-9 cyclohexylethan-1-ol 
• 134456-07-8 2-cyclohexyl-1-spiro<1,3-benzodioxole-2,1'-cyclohexane>-2-ethanol 
• 823-76-7 Cyclohexyl methyl ketone 
• 160950-60-7 (Z)-1-cyclohexyl-4-(trimethylsilyl)but-3-en-1-ol 
• 61414-09-3 1-cyclohexylethane-1,2-diol 
• 249621-37-2 4-cyclohexyl-2-(2,2-diethoxyethyl)-4-[[(dimethyl)isopropylsilyl]oxy]-butanenitrile 
• 126678-67-9 rac-3-cyclohexyl-3-hydroxypropionitrile 
• 59411-58-4 (R)-1-cyclohexylethane-1,2-diol 

Relevant academic research and scientific papers

CATALYTIC EPOXIDATION OF ALIPHATIC TERMINAL OLEFINS WITH SODIUM HYPOCHLORITE

Meso-tetra(halogenophenyl)porphyrinatomanganese complexes catalyze the epoxidation of terminal olefins by sodium hypochlorite at room temperature; moderate to good yields of epoxides are obtained.

Suicide inactivation of cytochrome P-450 model compounds by terminal olefins. 1. A mechanistic study of heme N-alkylation and expoxidation

Synthetic iron porphyrins are found to be useful models for the suicide inactivation of cytochrome P-450. The epoxidation of 1-alkenes, 1,1-disubstituted alkenes, and styrenes by meso-[tetrakis(2,6-dichlorophenyl)porphinatoiron(III) chloride [Fe(OCP)Cl] r

Micelle-based nanoreactors containing Ru-porphyrin for the epoxidation of terminal olefins in water

This contribution introduces a strategy to use Ru(II)-porphyrin complexes as catalysts for the epoxidation of alkenes in water. The design is based on shell cross-linked micelle-based nanoreactors with hydrophobic cores and hydrophilic shells as supports

Catalytic oxygen atom transfer promoted by tethered Mo(VI) dioxido complexes onto silica-coated magnetic nanoparticles

The preparation of three novel active and stable magnetic nanocatalysts for the selective liquid-phase oxidation of several olefins, has been reported. The heterogeneous systems are based on the coordination of cis-MoO2 moiety onto three different SCMNP@Si-(L1-L3) magnetically active supports, functionalized with silylated acylpyrazolonate ligands L1, L2 and L3. Nanocatalysts thoroughly characterized by ATR-IR spectroscopy, TGA and ICP-MS analyses, showed excellent catalytic performances in the oxidation of conjugated or unconjugated olefins either in organic or in aqueous solvents. The good magnetic properties of these catalytic systems allow their easy recyclability, from the reaction mixture, and reuse over five runs without significant decrease in the activity, either in organic or water solvent, demonstrating their versatility and robustness.

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.

Proton Switch in the Secondary Coordination Sphere to Control Catalytic Events at the Metal Center: Biomimetic Oxo Transfer Chemistry of Nickel Amidate Complex

High-valent metal-oxo species are key intermediates for the oxygen atom transfer step in the catalytic cycles of many metalloenzymes. While the redox-active metal centers of such enzymes are typically supported by anionic amino acid side chains or porphyrin rings, peptide backbones might function as strong electron-donating ligands to stabilize high oxidation states. To test the feasibility of this idea in synthetic settings, we have prepared a nickel(II) complex of new amido multidentate ligand. The mononuclear nickel complex of this N5 ligand catalyzes epoxidation reactions of a wide range of olefins by using mCPBA as a terminal oxidant. Notably, a remarkably high catalytic efficiency and selectivity were observed for terminal olefin substrates. We found that protonation of the secondary coordination sphere serves as the entry point to the catalytic cycle, in which high-valent nickel species is subsequently formed to carry out oxo-transfer reactions. A conceptually parallel process might allow metalloenzymes to control the catalytic cycle in the primary coordination sphere by using proton switch in the secondary coordination sphere.

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Co(II) Schiff base Complexes Encapsulated in the Nanopores of Zeolite Y as Heterogeneous Catalysts for Selective Epoxidation of Alkenes with Molecular Oxygen

Abstract: Co(II) macrocyclic Schiff base complex nanoparticles have been encapsulated in the nanopores of zeolite Y. The new Schiff base complexes entrapped in the nanoreactor of zeolite Y were characterized by several techniques: chemical analysis and spectroscopic methods (FT-IR, XRD, and DRS). These complexes (neat and encapsulated) were used for epoxidation of alkenes with O2 as oxidant in different solvents. The catalyst demonstrated excellent activity for a variety of alkenes in a mild, inexpensive and efficient protocol. Reaction parameters including temperature, catalyst amount and solvent were screened by reaction time. The recycling experiment results indicated that the catalysts were highly stable and maintained activity and selectivity even after being used for five cycles.

Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.

Dendrimer crown-ether tethered multi-wall carbon nanotubes support methyltrioxorhenium in the selective oxidation of olefins to epoxides

Benzo-15-crown-5 ether supported on multi-wall carbon nanotubes (MWCNTs) by tethered poly(amidoamine) (PAMAM) dendrimers efficiently coordinated methyltrioxorhenium in the selective oxidation of olefins to epoxides. Environmentally friendly hydrogen peroxide was used as a primary oxidant. Up to first and second generation dendrimer aggregates were prepared by applying a divergent PAMAM methodology. FT-IR, XRD and ICP-MS analyses confirmed the effective coordination of methyltrioxorhenium by the benzo-15-crown-5 ether moiety after immobilization on MWCNTs. The novel catalysts converted olefins to the corresponding epoxides in high yield without the use of Lewis base additives, or anhydrous hydrogen peroxide, the catalyst being stable for more than six oxidative runs. In the absence of the PAMAM structure, the synthesis of diols largely prevailed.