122210-64-4

Basic information

• Product Name: (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide
• CAS NO: 122210-64-4
• Molecular Weight: 174.243
• Mol File: 122210-64-4.mol
• Article Data: 211

Chemical Properties

• CAS DataBase Reference: (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide(122210-64-4)
• EPA Substance Registry System: (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide(122210-64-4)

Safety Data

• Hazardous Substances Data: 122210-64-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 771-98-2 1-Phenylcyclohexene 
• 93-59-4 Perbenzoic acid 
• 108-86-1 bromobenzene 
• 7722-84-1 dihydrogen peroxide 
• 100-58-3 phenylmagnesium bromide 
• 108-94-1 cyclohexanone 
• 40940-63-4 1-phenyl-2-bromo-1-hydroxycyclohexane 
• 1589-60-2 1-phenylcyclohexanol 
• 827-52-1 1-phenyl-1-cyclohexane 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 75-91-2 tert.-butylhydroperoxide 
• 19324-77-7 (+/-)-2c-chloro-1r-phenyl-cyclohexanol-⁽¹⁾ 

Downstream Products

• 101688-13-5 phenyl-2 t-(piperidino-1)-2 r-cyclohexanol 
• 2362-61-0 cis-2-phenylcyclohexanol 
• 129920-34-9 (1R^*,2S^*)-2-(methylamino)-1-phenylcyclohexane-1-ol 
• 17540-06-6 trans-2-(dimethylamino)-1-phenylcyclohexanol 
• 26524-28-7 phenylcyclohexylacetate 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 21573-69-3 1-phenyl-1-cyclopentanecarboxaldehyde 
• 94824-44-9 1-phenyl-2-piperidin-1-yl-cyclohexanol 
• 87258-30-8 6-oxo-6-phenylhexanal 
• 13286-66-3 trans-2-amino-1-phenyl-cyclohexanol-⁽¹⁾ 
• 52906-49-7 trans-2-amino-2-phenylcyclohexanol 
• 771-98-2 1-Phenylcyclohexene 
• 4556-09-6 2-phenylcyclohex-2-enone 
• 32363-86-3 2-phenylcyclohex-2-enol 

Relevant articles and documents

A novel chiral manganese-tetraamide macrocycle complex covalently attached to magnetite as recyclable catalyst for aerobic asymmetric epoxidation of olefins

A novel Mn complex containing N4-tetradentate tetraamide macrocyclic ligand (L) derived from chiral diethyl-2,3-benzylidene-L-tartrate and polyamidoamine dendrimer on Fe3O4@SiO2 surface was synthesized. The nanocomposite particles were investigated by SEM, XRD, VSM, EPR and FTIR. The nanocomposite showed high catalytic activity and selectivity for the epoxidation of linear terminal, cyclic and most of the aromatic olefins by O2 in the presence of isobutyraldehyde under mild conditions; epoxide selectivity 87–100%, enantiomeric excess 53–100%. The catalyst could be separated and recovered from the reaction system by applying an external magnetic field and reused for four cycles without the loss of activity after each cycle. Total TON of 16957 was obtained after four cycles.

Effect of the medium on the oxaziridinium-catalyzed enantioselective epoxidation

TRISPHAT salts of chiral iminium cations allow, in combination with 18-C-6, the use of biphasic CH2Cl2/water conditions, which can improve the enantioselectivity of the oxone-mediated epoxidation.

Polystyrene-supported triphenylarsines: Useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxide

The utility of both soluble (non-cross-linked) and insoluble (cross-linked) polystyrene-supported triphenylarsine reagents were examined. These reagents were prepared by standard radical polymerization methodology and used in palladium-catalyzed homocoupling reactions of aryl halides. The insoluble reagent was also used as a catalyst precursor in heterogeneous alkene epoxidation reactions in which aqueous hydrogen peroxide was the stoichiometric oxidant. For the aryl halide homocoupling reactions, both reagents worked well and afforded similar results. Unhindered aryl iodides afforded the best yields in the shortest reaction times compared to aryl bromides. The epoxidation reactions of unfunctionalized alkenes were not very efficient. This was probably due to the hydrophobicity of the polystyrene matrix, which did not swell in the reaction medium. Thus, since a microporous, gel-type polystyrene matrix was used, the majority of the arsine groups were inaccessible to the reaction components and therefore incapable of participating in catalysis.

Effect of pore size on the performance of mesoporous material supported chiral Mn(III) salen complex for the epoxidation of unfunctionalized olefins

A series of mesoporous MCM-41 and MCM-48 materials with different pore sizes were synthesized and used as supports to immobilize chiral Mn(III) salen complex. The heterogeneous catalysts were characterized by XRD, FT-IR, DR UV-vis, and N2 sorpt

Aerobic Stereoselective Oxidation of Olefins on a Visible-Light-Irradiated Titanium Dioxide-Cobalt-Ascorbic Acid Nanohybrid

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Heterogeneous asymmetric epoxidation of alkenes catalysed by a polymer- bound (pyrrolidine salen)manganese(III) complex

Excellent enantioselectivity (e.g. 92% ee for 2,2-dimethylchromene) has been achieved in heterogeneous asymmetric epoxidation using a polymer-bound (pyrrolidine salen)-manganese(III) complex; however, this polymeric catalyst underwent partial decompositio

Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed.

Asymmetric synthesis of conformationally constrained cis-1-amino-1-phenylcyclohexan-2-ol

A regio- and stereo-controlled synthesis of chiral cis-1-amino-1-phenylcyclohexan-2-ol is described. The optically pure diol 4 was converted to the ligand 8 in 80% yield.

Iminium salt catalysts for asymmetric epoxidation: The first high enantioselectivities

A highly enantioselective iminium salt catalyst has been prepared and tested in the catalytic asymmetric epoxidation of unfunctionalized alkenes, giving up to 95% ee, the highest ee yet reported for iminium salt-catalyzed epoxidation. Catalyst loadings as

Catalytic epoxidations with pyridinebis(oxazoline)-methyltrioxorhenium complexes and nitrogen-containing catalyst systems

The epoxidation of olefins with methyltrioxorhenium (MTO) in the presence of various chiral oxazolines and pyridinebis(oxazoline) ligands as well as achiral N-ligands has been investigated. By applying 1-octene as a model system, reaction conditions were optimized, and high yields and good chemoselectivity (>90 %) were achieved. By applying other aromatic and aliphatic olefins, similar chemoselectivities and up to 19 % enantioselectivity were obtained. The epoxidation of 1-octene using methyltrioxorhenium (MTO) in the presence of pyridinebis(oxazoline) and related ligands is reported. Although excellent chemoselectivity (>90 %) and good yields were obtained, low enantioselectivity was observed. Copyright

Dioxiranes Are the Active Agents in Ketone-Catalyzed Epoxidation with Oxone

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On the enantioselective olefin epoxidation by doubly bridged biphenyl azepine derivatives - Mixed tropos/atropos chiral biaryls

Diastereomeric doubly bridged biphenyl azepines, atropos at 20 °C and tropos at 80 °C, are precursors to effective iminium organocatalysts that are employed in the enantioselective epoxidation of prochiral olefins (up to 85% ee). The Royal Society of Chem

Chemistry of Oxaziridines. 4. Asymmetric Epoxidation of Unfunctionalized Alkenes Using Chiral 2-Sulfonyloxaziridines: Evidence for a Planar Transition State Geometry

Diastereomeric 2-sulfonyloxaziridines (-)-(S,S)-1 and (+)-(R,R)-2 epoxidize unfunctionalized olefins 3a-g, affording epoxides 4a-g with better enantioselectivity than do chiral peracids or hydroperoxides.The configuration of the oxaziridine three-membered ring controls the stereochemistry of the product.The mechanism of chiral recognition is largely determined by steric factors where the orientations of the oxaziridine three-membered ring and the alkene are planar in the transition state.

Organocatalysis of Asymmetric Epoxidation Mediated by Iminium Salts under Nonaqueous Conditions

The first nonaqueous conditions are described for catalytic asymmetric epoxidation mediated by iminium salt organocatalysts, providing ee values of up to 67%.

Nitrile-promoted alkene epoxidation with urea-hydrogen peroxide (UHP)

An efficient method for alkene epoxidation has been studied systematically using benzonitrile and the complex urea-hydrogen peroxide (UHP), which is an anhydrous form of hydrogen peroxide and has the potential to release hydrogen peroxide in a controlled manner and thus avoid the need to slowly add aqueous H2O2 to the reaction mixture. The absence of water in the reaction media was also beneficial, because it minimized undesired reactions of the oxidized products. A range of alkenes was epoxidized by this method, providing yields ranging from 79% to 96%. Copyright

Fighting Fenton Chemistry: A Highly Active Iron(III) Tetracarbene Complex in Epoxidation Catalysis

Organometallic Fe complexes with exceptionally high activities in homogeneous epoxidation catalysis are reported. The compounds display FeII and FeIII oxidation states and bear a tetracarbene ligand. The more active catalyst exhibits activities up to 183 000 turnovers per hour at room temperature and turnover numbers of up to 4300 at -30°C. For the FeIII complex, a decreased Fenton-type reactivity is observed compared with FeII catalysts reported previously as indicated by a substantially lower H2O2 decomposition and higher (initial) turnover frequencies. The dependence of the catalyst performance on the catalyst loading, substrate, water addition, and the oxidant is investigated. Under all applied conditions, the advantageous nature of the use of the FeIII complex is evident.

New organocatalysts for the asymmetric catalytic epoxidation of alkenes mediated by chiral iminium salts

New iminium salt organocatalysts for catalytic asymmetric epoxidation based upon dibenzazepinium salts are reported, providing ee of up to ca 60%.

Enantioselective olefin epoxidation using novel doubly bridged biphenyl azepines as catalysts

Enantiopure (diastereomeric) doubly bridged biphenyl azepines prepared from (S)-3,3-dimethylbutan-2-amine and (S)-1-phenylpropylamine can be - as a function of the exocyclic side chain - either effective catalysts for the enantioselective epoxidation of u

MoO2 Formed on Mesoporous Graphene Oxide: Efficient and Stable Catalyst for Epoxidation of Olefins

A novel mesoporous MoO2 composite supported on graphene oxide (m-MoO2/GO) has been designed and applied as an efficient epoxidation catalyst. The m-MoO2/GO composite was characterised by X-ray diffraction, Raman spectroscopy, X-ray photoelectron spectrosc

A New System for Catalytic Asymmetric Epoxidation Using Iminium Salt Catalysts

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Exploring structural effects of ketone catalysts on asymmetric epoxidation of olefins

Several ketone catalysts containing spiro ethers and lactones have been investigated for the asymmetric epoxidation of olefins. The results showed that substituents on the spiro ring of the ketone catalysts have profound effects on enantioselectivity. Res

Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation

A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation.

An efficient organic solvent-free methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide

Methyltrioxorhenium/3-methylpyrazole has proved to be an efficient catalytic system for epoxidation of alkenes with aqueous 35% H2O2 in excellent yields under organic solvent-free conditions. The yields of epoxides by the organic solvent-free epoxidation are comparable to those using CH2Cl2 as the organic solvent. The epoxidations of simple alkenes under organic solvent-free conditions are slower than those in CH2Cl2, while the epoxidations of alkenols such as citronellol are faster than those in CH2Cl2.

Selectivity enhancement for the Jacobsen - Katsuki epoxidation in fluorinated solvents

In 1,1,1,2,3,4,4,5,5,5-Decafluoropentane using 2-phenylpyridine N-oxide as donor ligand, the enantioselectivity of the Jacobsen - Katsuki epoxidation is improved up to 10% ee as compared to established protocols.

Catalytic asymmetric synthesis of epoxides mediated by chiral iminium salts

The catalytic asymmetric oxidation of unfunctionalised alkenes is achieved by a non-transition metal catalysed process; just 5 mol% of the binaphthyl-based iminium salt 1 is sufficient to catalyse the oxidation of alkenes to epoxides with moderate to good

Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.

Organocatalytic epoxidation and allylic oxidation of alkenes by molecular oxygen

Pyrrole-proline diketopiperazine (DKP) acts as an efficient mediator for the reduction of dioxygen by Hantzsch ester under mild conditions to allow the aerobic metal-free epoxidation of electron-rich alkenes. Mechanistic crossovers are underlined, explaining the dual role of Hantzsch ester as a reductant/promoter of the DKP catalyst and a simultaneous competitor for the epoxidation of alkenes when HFIP is used as a solvent. Expansion of this protocol to the synthesis of allylic alcohols was achieved by adding a catalytic amount of selenium dioxide as an additive, revealing a superior method to the classical application of t-BuOOH as a selenium dioxide oxidant.

Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide

The organocatalytic epoxidation of unactivated alkenes using aqueous hydrogen peroxide provides various indispensable products and intermediates in a sustainable manner. While formyl functionalities typically undergo irreversible oxidations when activating an oxidant, an atropisomeric two-axis aldehyde capable of catalytic turnover was identified for high-yielding epoxidations of cyclic and acyclic alkenes. The relative configuration of the stereogenic axes of the catalyst and the resulting proximity of the aldehyde and backbone residues resulted in high catalytic efficiencies. Mechanistic studies support a non-radical alkene oxidation by an aldehyde-derived dioxirane intermediate generated from hydrogen peroxide through the Payne and Criegee intermediates.