61393-19-9

Basic information

• Product Name: (2S)-2-cyclohexyloxirane
• Synonyms: (2S)-2-Cyclohexyloxirane; oxirane, 2-cyclohexyl-, (2S)-
• CAS NO: 61393-19-9
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.1962
• Mol File: 61393-19-9.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 167.497°C at 760 mmHg
• Flash Point: 41.48°C
• Density: 1.015g/cm³
• Vapor Pressure: 2.238mmHg at 25°C
• Refractive Index: 1.499
• CAS DataBase Reference: (2S)-2-cyclohexyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-cyclohexyloxirane(61393-19-9)
• EPA Substance Registry System: (2S)-2-cyclohexyloxirane(61393-19-9)

Safety Data

• Hazardous Substances Data: 61393-19-9(Hazardous Substances Data)

Usage

General Description

(2S)-2-cyclohexyloxirane, also known as trans-2-cyclohexyl-oxirane, is a chemical compound with the molecular formula C7H12O. It is a colorless liquid with a molecular weight of 112.17 g/mol. (2S)-2-cyclohexyloxirane is used in the synthesis of various organic compounds and is commonly employed as an intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It is also utilized as a reagent in organic chemistry reactions, such as in the preparation of chiral epoxide derivatives. Additionally, (2S)-2-cyclohexyloxirane has potential applications in the development of new materials and as a building block for the preparation of specialty chemicals. Overall, (2S)-2-cyclohexyloxirane plays a significant role in the field of organic synthesis and chemical manufacturing.

Upstream product

• 695-12-5 vinylcyclohexane 
• 61414-09-3 1-cyclohexylethane-1,2-diol 
• 823-76-7 Cyclohexyl methyl ketone 
• 3483-39-4 Cyclohexyloxirane 
• 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 
• 90202-27-0 (+/-)-2-chloro-1-cyclohexylethanol 
• 61475-31-8 (S)-hexahydromandelic acid 
• 97531-43-6 2-cyclohexyl-2-oxoethyl 4-methylbenzenesulfonate 
• 223429-17-2 (S)-1-cyclohexyl-2-oxoethyl benzoate 
• 111902-61-5 (2R,3R)-3-cyclohexyl-2,3-epoxypropan-1-ol 
• 61414-09-3 (S)-1-cyclohexyl-1,2-ethanediol 
• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 

Downstream Products

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

Relevant articles and documents

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.

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.

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 %.