27729-95-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 70-11-1 α-bromoacetophenone 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 22252-15-9 trans-4-methoxychalcone 
• 98-86-2 acetophenone 
• 637-69-4 4-Methoxystyrene 
• 100-52-7 benzaldehyde 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 33951-39-2 3-(4-methoxyphenyl)-2-phenyl-2-hydroxypropanoic 
• 6343-94-8 5-(4-methoxybenzyl)-5-phenylimidazolidine-2,4-dione 
• 60595-14-4 N-phenacyltrimethylammonium chloride 
• 22174-47-6 2-hydroxy-3-(4-methoxy-phenyl)-3-morpholin-4-yl-1-phenyl-propan-1-one 
• 79480-21-0 1-[5-(4-Methoxy-phenyl)-3-phenyl-pyrazol-1-yl]-phthalazine 
• 80883-97-2 1-(p-Sulfamylphenyl)-4-hydroxy-3-phenyl-5-p-methoxyphenyl-2-pyrazoline 
• 106002-85-1 3-(4-methoxyphenyl)-1-phenylpropane-1,2-dione 
• 766-76-7 benzoate 
• 71-47-6 formate 
• 123-11-5 4-methoxy-benzaldehyde 
• 76246-85-0 erythro-2-(4-methoxyphenyl)-1-phenyl-1,3-propanediol 
• 132178-17-7 3-hydroxy-3-(4-methoxyphenyl)-1-phenylpropane-1-one 
• 371961-34-1 2-hydroxy-3-methoxy-3-(4-methoxy-phenyl)-1-phenyl-propan-1-one 
• 851729-18-5 3-phenyl-5-(4-methoxyphenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.

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.

Application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric reaction

The invention relates to application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric epoxidation reaction of chalcone compounds. According to the application, alpha, beta-unsaturated ketone shown in a formula (1) and tert-butyl hydroperoxide react in the presence of organic alkali under the combined catalytic action of a chiral TADDOL ligand shown in a formula (3) and rare earth metal amide in an anhydrous, oxygen-free and protective atmosphere to obtain the chiral epoxy compound shown in the formula (2) after the reaction is completed, wherein R1 is selected from hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro or cyano, R2 is selected from phenyl, substituted phenyl, naphthyl, furyl or thienyl; R3 and R4 are respectively and independently selected from alkyl, phenyl or R3 and R4 and carbon atoms connected with R3 and R4 form naphthenic base; Ar is phenyl, substituted phenyl, biphenyl or naphthyl; the molecular formula of the rare earth metal amide is RE [N (SiMe3) 2] 3. The method has the advantages of wide substrate application range, high yield and high enantioselectivity.

Visible-Light-Driven Epoxyacylation and Hydroacylation of Olefins Using Methylene Blue/Persulfate System in Water

A visible-light-driven strategy for hydroacylation and epoxyacylation of olefins in water using methylene blue as photoredox catalyst and persulfate as oxidant is reported. In this unprecedented unified approach, two different transformations are accomplished using only one set of reagents. The method has a broad scope spanning a range of aromatic and aliphatic aldehydes as well as conjugated and nonconjugated olefins to deliver ketones and epoxyketones from abundant and inexpensive chemical feedstocks.

A highly enantioselective asymmetric Darzens reaction catalysed by proline based efficient organocatalysts for the synthesis of di- and tri-substituted epoxides

A new class of easily available and readily tunable proline based chiral organocatalysts was found to efficiently catalyse an unprecedented highly enantioselective asymmetric Darzens reaction of α-chloroketones and substituted α-chloroketones with various

Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant

Abstract: Various aromatic α, β-unsaturated ketones were successfully transformed into their corresponding epoxides using urea-2,2-dihydroperoxypropane as the oxygen source for the first time. The reactions were carried out under mild alkaline conditions at room temperature in high yields and short reaction times. Graphical Abstract: [Figure not available: see fulltext.]

Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant

1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane was used for the efficient and metal-free epoxidation of various α,β-unsaturated ketones, carried out under mild alkaline conditions at room temperature.

Electrochemically induced ring-opening/friedel-crafts arylation of chalcone epoxides catalyzed by a triarylimidazole redox mediator

The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med?+ and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med?+ initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.

Copper(II)triflate promoted highly chemoselective rearrangement of chalcone epoxides to β-keto aldehydes

Highly chemoselective rearrangement of chalcone epoxides to β-keto aldehydes using catalytic amount of Cu(OTf)2 (1 mol%) is presented. Copper(II)triflate is a relatively cheap, inexpensive and commercially available catalyst. In this rearrangement selective migration of the acyl group takes place. The presence of an electron donating group on either of the phenyl rings favors the reaction. However, the presence of an electron withdrawing CN group leads to the corresponding β-keto aldehyde, along with an aryl ketone which is obtained through deformylation of the primary product.

Metal-free, one-pot, sequential protocol for transforming ,-epoxy ketones to -hydroxy ketones and -methylene ketones

A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to β;-hydroxy ketones and α-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate (BF3·OEt2) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the β;-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the α-methylene ketone products can be carried out in one pot.