28098-67-1

Basic information

• Product Name: [S-(R*,S*)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane
• Synonyms: [S-(R*,S*)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane;(S)-2-Methyl-2-[(R)-4-methyl-3-cyclohexenyl]oxirane;(S)-2-Methyl-2β-[(R)-4-methyl-3-cyclohexen-1β-yl]oxirane
• CAS NO: 28098-67-1
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 248-839-3
• Mol File: 28098-67-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 197.3°C at 760 mmHg
• Flash Point: 67.2°C
• Appearance: /
• Density: 0.987g/cm³
• Vapor Pressure: 0.536mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: [S-(R*,S*)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: [S-(R*,S*)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane(28098-67-1)
• EPA Substance Registry System: [S-(R*,S*)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane(28098-67-1)

Safety Data

• Hazardous Substances Data: 28098-67-1(Hazardous Substances Data)

Usage

Description

[S-(R,S)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane is a chemical compound with the molecular formula C10H16O. It is an epoxide, also known as a cyclic ether, with a three-membered ring containing one oxygen atom. This chiral molecule has non-superimposable mirror image isomers and is commonly used as a building block in the synthesis of pharmaceuticals and other complex organic compounds. It is also utilized as a reagent in organic chemistry reactions, such as in the formation of carbon-carbon bonds.

Uses

Used in Pharmaceutical Industry:
[S-(R,S)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane is used as a building block for the synthesis of pharmaceuticals due to its versatile reactivity and synthetic utility. It plays a crucial role in the development of new drugs and medicines.
Used in Agrochemical Industry:
In the agrochemical industry, [S-(R,S)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane is used as a component in the creation of various agrochemical products, contributing to its effectiveness and performance.
Used in Material Science Industry:
[S-(R,S)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane is also used in the material science industry, where it serves as a key component in the development of advanced materials with specific properties and applications.
Used as a Reagent in Organic Chemistry:
[S-(R,S)]-2-methyl-2-(4-methylcyclohex-3-enyl)oxirane is used as a reagent in organic chemistry reactions, particularly in the formation of carbon-carbon bonds, which are essential for creating a wide range of organic compounds.

InChI:InChI=1/C10H16O/c1-8-3-5-9(6-4-8)10(2)7-11-10/h3,9H,4-7H2,1-2H3

Upstream product

• 4648-54-8 trimethylsilylazide 
• 184488-93-5 (R)-8,9-limonene oxide 
• 5989-27-5 D-limonene 
• 50429-63-5 (1S,2S,4R)-1,2-dibromo-p-menth-8-ene 
• 107090-89-1 (4R,8R)-8-hydroxy-p-menth-1-en-9-yl p-toluenesulfonate 
• 200723-09-7 (4R,8Ξ)-p-menth-1-ene-8,9-diol 

Downstream Products

• 96-08-2 (1S,4R,6R)-1-methyl-4-((S)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane 
• 96-08-2 (1R,4R,6S)-1-methyl-4-(S)-2-methyloxiran-2-yl-7-oxa-bicyclo[4.1.0]heptane 
• 96-08-2 (1S,4R,6R)-1-methyl-4-((R)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane 
• 96-08-2 (1R,4R,6S)-1-methyl-4-((R)-2-methyloxiran-2-yl)-7-oxa-bicyclo[4.1.0]heptane 

Relevant articles and documents

Limonene epoxidation with H2O2 promoted by Al2O3: Kinetic study, experimental design

A highly efficient oxidation of limonene with hydrogen peroxide promoted by cheap aluminum oxide has been studied. The reaction is a rare example of the epoxidation promoted by a derivative of non-transition metal having a single stable non-zero oxidation state (SSOS metal), and it affords epoxides which are highly valuable products (fragrances, food additives and monomers). Typically, ethyl acetate at 80 °C was used as a solvent. The experimental data have been described by the proposed kinetic scheme. The optimization of the limonene epoxidation using a 23 experimental design has been carried out.

Design, preparation, and study of catalytic gated baskets

We report a diastereoselective synthetic method to obtain a family of catalytic molecular baskets containing a spacious cavity (～570 A3). These supramolecular catalysts were envisioned, via the process of gating, to control the access of substrates to the embedded catalytic center and thereby modulate the outcome of chemical reactions. In particular, gated basket 1 comprises a porphyrin floor fused to four phthalimide side walls each carrying a revolving aromatic gate. With the assistance of 1H NMR and UV-vis spectroscopy, we demonstrated that the small 1-methylimidazole guest (12, 94 A3) would coordinate to the interior while the larger 1,5-diadamantylimidazole guest (14, 361 A3) is relegated to the exterior of basket Zn(II)-1. Subsequently, we examined the epoxidation of differently sized and shaped alkenes 18-21 with catalytic baskets 12 in-Mn(III)-1 and 14out-Mn(III)-1 in the presence of the sacrificial oxidant iodosylarene. The epoxidation of cis-stilbene occurred in the cavity of 14out-Mn(III)-1 and at the outer face of 12 in-Mn(III)-1 with the stereoselectivity of the two transformations being somewhat different. Importantly, catalytic basket 14out-Mn(III) -1 was capable of kinetically resolving an equimolar mixture of cis-2-octene 20 and cis-cyclooctene 21 via promotion of the transformation in its cavity.

Efficient epoxidation of electron-deficient alkenes with hydrogen peroxide catalyzed by [γ-PW10O38V2(μ-OH) 2]3-

A divanadium-substituted phosphotungstate, [γ-PW10O 38V2(μ-OH)2]3- (I), showed the highest catalytic activity for the H2O2-based epoxidation of allyl acetate among vanadium and tungsten complexes with a turnover number of 210. In the presence of I, various kinds of electron-deficient alkenes with acetate, ether, carbonyl, and chloro groups at the allylic positions could chemoselectively be oxidized to the corresponding epoxides in high yields with only an equimolar amount of H2O2 with respect to the substrates. Even acrylonitrile and methacrylonitrile could be epoxidized without formation of the corresponding amides. In addition, I could rapidly (min) catalyze epoxidation of various kinds of terminal, internal, and cyclic alkenes with H;bsubesubbsubesub& under the stoichiometric conditions. The mechanistic, spectroscopic, and kinetic studies showed that the I-catalyzed epoxidation consists of the following three steps: 1) The reaction of I with H;bsubesubbsubesub& leads to reversible formation of a hydroperoxo species [I;circbsubesubbsubesubbsubesubcirccircbsupesup& (II), 2) the successive dehydration of II forms an active oxygen species with a peroxo group [ 2:2-O2)]3- (III), and 3) III reacts with alkene to form the corresponding epoxide. The kinetic studies showed that the present epoxidation proceeds via III. Catalytic activities of divanadium-substituted polyoxotungstates for epoxidation with H 2O2 were dependent on the different kinds of the heteroatoms (i.e., Si or P) in the catalyst and I was more active than [γ-SiW10O38V2(μ-OH)2] 4-. On the basis of the kinetic, spectroscopic, and computational results, including those of [γ-SiW10O38V 2(μ-OH)2]4-, the acidity of the hydroperoxo species in II would play an important role in the dehydration reactivity (i.e., k3). The largest k3 value of I leads to a significant increase in the catalytic activity of I under the more concentrated conditions. Copyright