5814-81-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Methoxyphenyl)-3-phenyloxirane is used as a pharmaceutical compound for its potential therapeutic properties. As a stilbenoid, it may exhibit various biological activities, such as antioxidant, anti-inflammatory, and anticancer effects, making it a promising candidate for the development of new drugs and treatments.
Used in Cosmetic Industry:
2-(4-Methoxyphenyl)-3-phenyloxirane is used as an active ingredient in cosmetics for its potential skin benefits. Its antioxidant properties may help protect the skin from oxidative stress and environmental damage, while its anti-inflammatory effects may contribute to reducing skin irritation and redness.
Used in Food Industry:
2-(4-Methoxyphenyl)-3-phenyloxirane can be used as a natural preservative in the food industry. Its antioxidant properties may help extend the shelf life of food products by preventing oxidation and spoilage, ensuring freshness and quality.
Used in Agricultural Industry:
2-(4-Methoxyphenyl)-3-phenyloxirane can be employed as a natural pesticide or fungicide in agriculture. Its antimicrobial and antifungal properties may help protect crops from diseases and pests, promoting healthy growth and increased yield.

Upstream product

• 17903-41-2 phenyl(trimethylsilyl)methyl bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 78733-51-4 2-(4-methoxyphenyl)-5-phenyl-1,3-dioxolan-4-one 
• 1657-53-0 cis-4-methoxystilbene 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 
• 1694-19-5 p-methoxystilbene 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 27992-27-4 sodium 2-benzylidene-1-tosylhydrazin-1-ide 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 143207-82-3 cis-1-(2,4-dimethoxyphenyl)-2-phenylethylene 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 5197-95-5 benzyltriethylammonium bromide 

Downstream Products

• 611-94-9 4-Methoxybenzophenone 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 65-85-0 benzoic acid 
• 107246-01-5 (2R,5S)-2-(4-Methoxy-phenyl)-5-phenyl-furan-3,3,4,4-tetracarbonitrile 
• 107246-02-6 (2R,5R)-2-(4-Methoxy-phenyl)-5-phenyl-furan-3,3,4,4-tetracarbonitrile 
• 89902-48-7 3-(4-methoxyphenyl)-5-phenyltrioxolane 
• 24845-40-7 2-(4-methoxyphenyl)acetophenone 
• 16343-36-5 2-(4-methoxy-phenyl)-2-phenylacetaldehyde 
• 56913-16-7 2-bromo-1-phenyl-2-(4'-methoxyphenyl)-1-ethanone 
• 1449779-36-5 2-(4-methoxyphenyl)-1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethanone 
• 5422-47-9 1-(4-methoxyphenyl)-2-phenylethan-1-ol 
• 20498-67-3 1-phenyl-2-(4-methoxylphenyl)ethanol 

Relevant academic research and scientific papers

Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**

Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.

Effect of substituents on TiO2 photocatalytic oxidation of trans-stilbenes

Photocatalytic reaction of trans-stilbene on TiO2 particles produces benzaldehyde with high selectivity in acetonitrile-water mixed solvent. Introduction of electron-donating substituents to the benzene rings accelerated the reaction. On the other hand, the rate was decelerated by electron-withdrawing substituents. These results suggest that the reaction proceeds by hydroperoxo or hydroperoxy, which were formed on TiO2 surface by UV irradiation, rather than free OH radicals.

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

A one-pot synthesis of epoxides from commercially available benzyl alcohols and aldehydes is described. The reaction proceeds through in situ generation of sulfonium salts from benzyl alcohols and their subsequent deprotonation for use in Corey–Chaykovsky epoxidation of aldehydes. The generality of the method is exemplified by the synthesis of 34 epoxides that were made from an array of electronically and sterically varied alcohols and aldehydes.

Benzylic Ammonium Ylide Mediated Epoxidations

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; Experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF 4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf 2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3 equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5 mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Br?nsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration

The Lewis-acid catalyzed rearrangement of parent trans-stilbene oxide 1 was studied with M(OTf)3/DCM and M(OTf)3/[BMIM][BF4] (M = Bi, Al, Ga, Sc, and Yb; [BMIM] = butylmethylimidazolium) and Zn(NTf2)2, and with Bi(OTf)3/[BMIM][X] (X = NTf2, OTf, PF6, and BF4), employing 5 mol% of catalyst. Selective formation of 2,2-dipheylacetaldehyde 2 (phenyl migration product) was observed in all cases, with Bi(OTf)3 proving most efficient. The rearrangement of 1 was also effected in [BMIM][X] (X = NTf2, OTf, PF6, and BF4) without an added catalyst under microwave MW irradiation, and X = PF6 gave the highest yield and selectivity. Efficient and selective rearrangement of 1-2 was also observed with 0.1-0.3equiv. of [BMIM(SO3H)][OTf] in DCM and in [BMIM][X]. A substituent effect study was performed with a series of singly substituted 1,2-diphenyl oxiranes (with X = OMe, Me, F, CN, and NO2) with 5mol% Bi(OTf)3 in DCM and in [BMIM][NTf2]. Notable formation of ketones was observed with the NO2 and CN derivatives. Competing formation of ketones was also observed in [BMIM][PF6] under MW and under Br?nsted acid catalysis with [BMIM(SO3H)][OTf] in DCM and in [BMIM][NTf2]. The aryl versus H migration was studied computationally by DFT and MP2 methods and by including solvation effects (IEFPCM).

Four metalloporphyrinic frameworks as heterogeneous catalysts for selective oxidation and aldol reaction

Four porous metalloporphyrinic framework materials, [(CH3) 2NH2][Zn2(HCOO)2(Mn III-TCPP)]·5DMF·2H2O (1; H6TCPP = tetrakis(4-carboxyphenyl)porphyrin), [(CH3)2NH 2][Cd2(HCOO)2(MnIII-TCPP)] ·5DMF·3H2O (2), [Zn2(HCOO)(Fe III(H2O)-TCPP)]·3DMF·H2O (3), and [Cd3(H2O)6(μ2-O)(Fe III-HTCPP)2]·5DMF (4) were synthesized by heating a mixture of MIIICl-H4TCPP (M = Mn and Fe) and M′ (M′ = Zn or Cd) nitrate in a mixed solvent of DMF and acetic acid. Compounds 1-3 are built up from M′2(COO)4 paddle-wheel subunits bridged by MIII-TCPP and formate ligands to form their 3D connections. The formate pillar heterogeneously connects with M and M′ cations in 1 and 2 and homogeneously joins M′ cations in 3. The μ2-O bridged FeIII-HTCPP dimer performs as a decadentate ligand to link 10 cadmium cations for the formation of an interesting 3D coordination network of 4. The four porphyrinic frameworks present interesting catalytic properties in the selective epoxidation of olefins, oxidation of cyclohexane, and intermolecular aldol reaction of aldehydes and ketones.

Visible light-mediated oxidative quenching reaction to electron-rich epoxides: Highly regioselective synthesis of α-bromo (di)ketones and mechanism study

A novel and simple procedure was developed for the regioselective synthesis of α-bromo (di)ketones from electron-rich epoxides via visible light photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved under mild conditions. Moreover, the possible reaction mechanism was proposed and further supported by control experiments.

Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: Extensive studies to map out scope, limitations, and rationalization of diastereo- and enantioselectivities

The chiral sulfide, isothiocineole, has been synthesized in one step from elemental sulfur, γ-terpinene, and limonene in 61% yield. A mechanism involving radical intermediates for this reaction is proposed based on experimental evidence. The application of isothiocineole to the asymmetric epoxidation of aldehydes and the aziridination of imines is described. Excellent enantioselectivities and diastereoselectivities have been obtained over a wide range of aromatic, aliphatic, and α,β-unsaturated aldehydes using simple protocols. In aziridinations, excellent enantioselectivities and good diastereoselectivities were obtained for a wide range of imines. Mechanistic models have been put forward to rationalize the high selectivities observed, which should enable the sulfide to be used with confidence in synthesis. In epoxidations, the degree of reversibility in betaine formation dominates both the diastereoselectivity and the enantioselectivity. Appropriate tuning of reaction conditions based on understanding the reaction mechanism enables high selectivities to be obtained in most cases. In aziridinations, betaine formation is nonreversible with semistabilized ylides and diastereoselectivities are determined in the betaine forming step and are more variable as a result.

Enantioselective synthesis of (thiolan-2-yl)diphenylmethanol and its application in asymmetric, catalytic sulfur ylide-mediated epoxidation

This work describes an expeditious and efficient preparation of enantiopure (thiolan-2-yl)diphenylmethanol (2) featuring a double nucleophilic substitution and Shi epoxidation as key steps. One of the applications of its benzyl ether derivative to asymmetric sulfur ylide-mediated epoxidation with up to 92% ee (14 examples) was also demonstrated herein.