10152-58-6

Basic information

• Product Name: 2,2-diMethyl-3-phenyloxirane
• Synonyms: 2,2-diMethyl-3-phenyloxirane
• CAS NO: 10152-58-6
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20168
• Mol File: 10152-58-6.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 206.6°C at 760 mmHg
• Flash Point: 73.5°C
• Appearance: /
• Density: 1.008g/cm³
• Vapor Pressure: 0.338mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 2,2-diMethyl-3-phenyloxirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-diMethyl-3-phenyloxirane(10152-58-6)
• EPA Substance Registry System: 2,2-diMethyl-3-phenyloxirane(10152-58-6)

Safety Data

• Hazardous Substances Data: 10152-58-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2691, 1984 DOI: 10.1016/S0040-4039(01)81264-8

InChI:InChI=1/C10H12O/c1-10(2)9(11-10)8-6-4-3-5-7-8/h3-7,9H,1-2H3

Upstream product

• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 83569-58-8 2-bromo-2-methyl-1-phenylpropan-1-ol 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 100-52-7 benzaldehyde 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 42711-88-6 S-benzyltetrahydrothiophenium chloride 
• 67-64-1 acetone 
• 1774-47-6 trimethylsulfoxonium iodide 
• 103-79-7 1-phenyl-acetone 
• 107167-08-8 1-bromo-1-chloropropane 
• 594-16-1 2,2-dibromopropane 
• 2310-98-7 2-bromo-2-chloropropane 
• 98-87-3 benzylidene dichloride 

Downstream Products

• 20907-13-5 2-methyl-1-phenylpropane-1,2-diol 
• 110480-87-0 (R)-1-amino-2-methyl-1-phenyl-propan-2-ol 
• 100-86-7 2-Methyl-1-phenyl-2-propanol 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 1284239-88-8 2-(2-(diphenylphosphoryl)phenyl)-5,5-dimethyl-4-phenyl-4,5-dihydrooxazole 
• 1284239-92-4 2-(2-(diphenylphosphino)phenyl)-5,5-dimethyl-4-phenyl-4,5-dihydrooxazole 
• 36746-48-2 5,5-dimethyl-2,4-diphenyl-4,5-dihydrooxazole 
• 103729-80-2 2-methyl-1-phenylprop-2-en-1-ol 
• 25982-72-3 2-methyl-3-phenyl-but-3-en-2-ol 
• 7473-98-5 2-hydroxy-2-methylpropiophenone 
• 769-59-5 3-phenyl-butan-2-one 
• 3805-10-5 2,2-(dimethyl)-2-phenylacetaldehyde 
• 83205-08-7 tert-Butyl-(2-iodo-1,1-dimethyl-2-phenyl-ethoxy)-dimethyl-silane 
• 83205-07-6 1-tert-butyldimethylsilyloxy-1-phenyl-2-methylprop-2-ene 

Relevant articles and documents

Microbiological transformations 32: Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxides and vicinal diols: Application to substituted styrene oxide derivatives

The biohydrolyses of various substituted styrene oxide derivatives using the fungi Aspergillus niger or Beauveria sulferescens are described. The results obtained show that this methodology allows the preparation of enantiomerically enriched epoxides and diols via enantioselective and regioselective hydration. The comparative study of the results obtained suggests that these hydrolyses operate following different mechanisms and a model of the corresponding active sites is proposed.

Effect of the Ligand Backbone on the Reactivity and Mechanistic Paradigm of Non-Heme Iron(IV)-Oxo during Olefin Epoxidation

The oxygen atom transfer (OAT) reactivity of the non-heme [FeIV(2PyN2Q)(O)]2+ (2) containing the sterically bulky quinoline-pyridine pentadentate ligand (2PyN2Q) has been thoroughly studied with different olefins. The ferryl-oxo complex 2 shows excellent OAT reactivity during epoxidations. The steric encumbrance and electronic effect of the ligand influence the mechanistic shuttle between OAT pathway I and isomerization pathway II (during the reaction stereo pure olefins), resulting in a mixture of cis-trans epoxide products. In contrast, the sterically less hindered and electronically different [FeIV(N4Py)(O)]2+ (1) provides only cis-stilbene epoxide. A Hammett study suggests the role of dominant inductive electronic along with minor resonance effect during electron transfer from olefin to 2 in the rate-limiting step. Additionally, a computational study supports the involvement of stepwise pathways during olefin epoxidation. The ferryl bend due to the bulkier ligand incorporation leads to destabilization of both (Formula presented.) and (Formula presented.) orbitals, leading to a very small quintet–triplet gap and enhanced reactivity for 2 compared to 1. Thus, the present study unveils the role of steric and electronic effects of the ligand towards mechanistic modification during olefin epoxidation.

PALLADIUM(II)-CATALYZED EPOXIDATION OF OLEFINS WITH α-SILYLOXYALKYL PEROXYBENZOATES

A novel oxygen-atom-transfer reaction from α-silyloxyalkyl peroxybenzoate to olefins by palladium(II) catalyst to give epoxides has been described.

Development of a Ruthenium-Catalyzed Asymmetric Epoxidation Procedure with Hydrogen Peroxide as the Oxidant

-

Hydrocarbon oxidation catalyzed by manganese and iron complexes with the hexadentate ligand N,N′-di(ethylacetate)-N,N′-bis(2-pyridyl-methyl)- 1, 2-ethanediamine

Analogs of recently reported manganese and iron catalysts for alkene and alkane oxidation reactions have been prepared with the potentially hexadentate ligand N,N′-di(ethylacetate)-N,N′-bis(2-pyridylmethyl)-1, 2-ethanediamine (debpn). The Mn(II) and Fe(II) complexes, which were previously found to be hepta-coordinate in the solid state, are capable of catalyzing alkene epoxidation and aliphatic C-H activation reactions, although these activities are inferior to those of related complexes with less coordinating ligands. The hydrocarbon oxidation catalyzed by iron is more severely disrupted. Cyclic voltammetry indicates that the +2 oxidation states for both debpn complexes' metal ions are stabilized by the two additional chelate arms. Product analysis of the C-H activation and olefin epoxidation chemistries suggest that ligand-substrate steric interactions may exert additional inhibitory effects on the reactivity for the manganese catalysts.

-

-

Electric Birefringences and Molecular Conformations of 2-Aryloxirans in Solution

Electric birefringence and dipole moment measurements have been made for five aryloxirans as solutes at 298 K.The data are analysed to obtain informations on the preferred solution-state conformations taking into account electronic and steric interactions

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.

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.