61393-19-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-2-cyclohexyloxirane is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the production of a range of medicinal compounds.
Used in Agrochemical Industry:
(2S)-2-cyclohexyloxirane is used as an intermediate in the production of agrochemicals, aiding in the creation of substances that help protect and enhance crop yields.
Used in Fine Chemicals Production:
(2S)-2-cyclohexyloxirane is used as an intermediate for the synthesis of other fine chemicals, playing a role in the development of specialty products.
Used in Organic Chemistry Research:
(2S)-2-cyclohexyloxirane is used as a reagent in organic chemistry reactions, such as in the preparation of chiral epoxide derivatives, which are important for the synthesis of enantiomerically pure compounds.
Used in Material Science:
(2S)-2-cyclohexyloxirane has potential applications in the development of new materials, serving as a building block for the preparation of specialty chemicals and contributing to advances in material science.

Upstream product

• 695-12-5 vinylcyclohexane 
• 139040-39-4 1,1,1-trichloro(cyclohexyl)ethan-2-one 
• 61414-09-3 1-cyclohexylethane-1,2-diol 
• 3483-39-4 Cyclohexyloxirane 
• 61414-09-3 (S)-1-cyclohexyl-1,2-ethanediol 
• 111902-61-5 (2R,3R)-3-cyclohexyl-2,3-epoxypropan-1-ol 
• 223429-17-2 (S)-1-cyclohexyl-2-oxoethyl benzoate 
• 90202-27-0 (+/-)-2-chloro-1-cyclohexylethanol 
• 823-76-7 Cyclohexyl methyl ketone 
• 111324-03-9 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ⁵,4Λ⁵-catenadi(phosphazene) 
• 2043-61-0 cyclohexanecarbaldehyde 
• 56077-28-2 Bromomethyl cyclohexyl ketone 
• 61475-31-8 (S)-hexahydromandelic acid 
• 97531-43-6 2-cyclohexyl-2-oxoethyl 4-methylbenzenesulfonate 

Downstream Products

• 79015-64-8 (S)-1-Cyclohexyl-4-trimethylsilanyl-but-3-yn-1-ol 
• 887605-52-9 (R)-1-cyclohexyl-4-(trimethylsilyl)but-3-yn-1-ol 
• 120850-91-1 (S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol 

Relevant academic research and scientific papers

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.

Ambient-Pressure Asymmetric Preparation of S,S -DICHED, a C 2 -Symmetrical Director for Matteson Reactions

A synthesis of S, S -DICHED (dicyclohexylethane-1,2-diol), a C 2 -symmetrical chiral director for Matteson homologations, is described. It relies on the insertion of lithiated S -2-cyclohexyloxirane into cyclohexylboronic acid pinacol ester and proceeds in three linear steps from readily available starting materials. No step requires chromatography or any specialized equipment.

Photocatalytic Asymmetric Epoxidation of Terminal Olefins Using Water as an Oxygen Source in the Presence of a Mononuclear Non-Heme Chiral Manganese Complex

Photocatalytic enantioselective epoxidation of terminal olefins using a mononuclear non-heme chiral manganese catalyst, [(R,R-BQCN)MnII]2+, and water as an oxygen source yields epoxides with relatively high enantioselectivities (e.g., up to 60% enantiomeric excess). A synthetic mononuclear non-heme chiral Mn(IV)-oxo complex, [(R,R-BQCN)MnIV(O)]2+, affords similar enantioselectivities in the epoxidation of terminal olefins under stoichiometric reaction conditions. Mechanistic details of each individual step of the photoinduced catalysis, including formation of the Mn(IV)-oxo intermediate, are discussed on the basis of combined results of laser flash photolysis and other spectroscopic methods.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Catalytic Enantioselective Conversion of Epoxides to Thiiranes

A highly efficient and enantioselective Br?nsted acid catalyzed conversion of epoxides to thiiranes has been developed. The reaction proceeds in a kinetic resolution, furnishing both epoxide and thiirane in high yields and enantiomeric purity. Heterodimer formation between the catalyst and sulfur donor affords an effective way to prevent catalyst decomposition and enables catalyst loadings as low as 0.01 mol %.

Titanium cis-1,2-diaminocyclohexane (cis-DACH) salalen catalysts for the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide

Chiral Ti salalen complexes catalyze the asymmetric epoxidation of terminal non-conjugated olefins with hydrogen peroxide. Modular ligands based on cis-1,2-diaminocyclohexane (cis-DACH) were developed, giving high yields and enantiomeric excesses (ee, up to 96%) at catalyst loadings as low as 0.1-0.5mol%, and even under solvent-free conditions.

A mononuclear manganese complex of a tetradentate nitrogen ligand - Synthesis, characterizations, and application in the asymmetric epoxidation of olefins

A new chiral manganese complex (C1) bearing a tetradentate nitrogen ligand containing chiral bipyrrolidine and benzimidazole moieties was prepared. The structure of C1 was confirmed by ESI-MS and crystallography. This manganese complex is an active catalyst for the asymmetric epoxidation of various olefins with excellent conversion (up to 99%) and high enantiomeric excess (up to 96%ee) with hydrogen peroxide as the oxidant in the presence of 2-ethylhexanoic acid or acetic acid. Compared with previous structurally similar manganese complexes with different diamine backbones (C2, cyclohexanediamine; C3, diamine from L-proline), C1 showed improved asymmetric induction, especially for simple olefins such as styrene derivatives and substituted chromene. The possible reasons for the improvement of the ee values are discussed in the text on the basis of the crystal structures of the manganese complexes.

Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: Enantioselective epoxidation of terminal non-conjugated olefins with H 2O2

Terminal, non-conjugated olefins, such as 1-octene, are difficult to epoxidize asymmetrically. Ti salalen complexes based on cis-1,2- diaminocyclohexane catalyze this demanding reaction giving high yields and enantioselectivities (up to 95 % ee), with H2O2 as the oxidant. The X-ray structures of the μ-oxo and peroxo complexes shed light on the coordination behavior of this novel class of ligands.

Highly enantioselective ylide-mediated synthesis of terminal epoxides

The highly efficient asymmetric epoxidation of aldehydes by methylene transfer is now possible using new sulfonium salts. This journal is

Biaryl-bridged salalen ligands and their application in titanium-catalyzed asymmetric epoxidation of olefins with aqueous H2O2

A series of biaryl-bridged salalen ligands together with their titanium complexes have been designed and synthesized. The Ti complexes could serve as highly efficient catalysts for the asymmetric epoxidation of a wide range of olefins, giving the corresponding epoxides with high ee values. A biaryl-bridged salalen titanium complex was developed and used in the enantioselective epoxidation of a range of olefins with aqueous hydrogen peroxide as the oxidant. Notably, the intramolecular dinuclear Ti catalyst possessing a biaryl bridge is highly efficient for the reaction, especially using terminal aromatic olefins as substrates.