18873-03-5

Usage

InChI:InChI=1/C16H14O3/c1-18-13-9-7-11(8-10-13)14(17)16-15(19-16)12-5-3-2-4-6-12/h2-10,15-16H,1H3

Upstream product

• 22966-19-4 trans-4'-methoxychalcone 
• 959-23-9 4'-methoxychalcone 
• 100-52-7 benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 132455-51-7 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid 4-methoxy-phenyl ester 
• 132455-51-7 (2R,3S)-3-Phenyl-oxirane-2-carboxylic acid 4-methoxy-phenyl ester 
• 70265-89-3 (4S,5R)-3-(4-Methoxy-phenyl)-5-phenyl-4,5-dihydro-isoxazol-4-ol 
• 132455-51-7 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid 4-methoxy-phenyl ester 
• 127634-33-7 3-Bromo-2-hydroxy-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one 
• 22464-03-5 erythro-3-Chlor-2-hydroxy-1-(4-methoxyphenyl)-3-phenyl-propan-1-on 
• 22464-03-5 threo-3-Chlor-2-hydroxy-1-(4-methoxyphenyl)-3-phenyl-propan-1-on 
• 99442-76-9 3-Fluoro-2-hydroxy-1-(4-methoxy-phenyl)-3-phenyl-propan-1-one 
• 93011-61-1 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanal 
• 4136-21-4 p-methoxybenzoylmethanol 
• 4927-44-0 5-Benzyl-5-(4-methoxy-phenyl)-imidazolidine-2,4-dione 
• 32664-28-1 3-(4-methoxyphenyl)-5-phenyl-1H-pyrazole 
• 959-23-9 4'-methoxychalcone 

Relevant academic research and scientific papers

Asymmetric epoxidation of α,β-unsaturated ketones via an amine-thiourea dual activation catalysis

A simple asymmetric epoxidation method is developed to effectively synthesize chiral α-carbonyl epoxides through an amine-thiourea dual activation catalysis. In this method, TBHP, as an oxidant, determined the reaction rate, and the chiral amine-thiourea catalyst effectively controlled the stereoselectivity of the reaction, and KOH promoted deprotonation. 22 examples of α,β-unsaturated ketones with various substituent groups are smoothly converted into α-carbonyl epoxides with moderate to excellent enantiomeric excess.

Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by rare-earth metal amides RE[N(SiMe3)2]3with chiral TADDOL ligands

The catalytic asymmetric epoxidation of α,β-unsaturated ketones by tert-butylhydroperoxide (TBHP) has been well established using rare-earth metal amides RE[N(SiMe3)2]3 (RE = La(1), Nd(2), Sm(3), Y(4), Yb(5)) with chiral TADDOL ligands. It was found that

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.

Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid

A novel manganese catalyst bearing an l-proline-derived N4 ligand has been developed for enabling acid-free asymmetric epoxidation of olefins with tert-butyl hydroperoxide as the oxidant. A variety of olefins that are well-matched in size with the ligand

Chiral calcium-catalyzed asymmetric epoxidation reactions using hydrogen peroxide as the terminal oxidant

Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivitie

Syntheses, Structures, and Catalytic Activities of the Anionic Heterobimetallic Rare-Earth Metal Complexes Supported by Pyrrolyl-Substituted 1,2-Diimino Ligands

A series of the anionic heterobimetallic rare-earth metal complexes supported by trans- or chiral pyrrolyl-substituted 1,2-diimino ligands were synthesized in good yields via reactions of [(Me3Si)2N]3RE(μ-Cl)Li(THF)3

Asymmetric Epoxidation of Olefins with H2O2 Catalyzed by a Bioinspired Aminopyridine N4 Iron Complex

An iron complex with a chiral aminopyridine N4 ligand bearing strong electron-donating and bulky morpholine groups on the ligand is synthesized and characterized. The iron complex serves to efficiently catalyze the asymmetric epoxidation of various olefins by employing aqueous hydrogen peroxide as the green oxidant, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 93 % yield and 99.9 % ee). Owing to the introduction of morpholine functional groups on the ligand, the Fe-catalyzed reaction can proceed with a catalytic amount of the carboxylic acid partner (3 mol %).

Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

Quest for Efficient Catalysts based on Zinc tert-Butyl Peroxides for Asymmetric Epoxidation of Enones: C2- vs C1-Symmetric Auxiliaries

Zinc tert-butyl peroxide-based catalysts for the asymmetric epoxidation of enones using tert-butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′-bidentate ligands, C2-symmetric bisoxazolinates and C1-symmetric enaminooxazolinates, revealed excellent performance of C1-symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96% yield, 91% ee).