30626-00-7

Upstream product

• 106-96-7 propargyl bromide 
• 105-07-7 4-cyanobenzaldehyde 
• 10406-25-4 4-aminobenzyl cyanide 
• 67-64-1 acetone 
• 73291-09-5 4-chloromethylbenzaldehyde 
• 78-95-5 chloroacetone 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 78-94-4 methyl vinyl ketone 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 74529-94-5 4-(4-Cyanophenyl)-3,4-dihydro-2-methyl-2H-pyrano<3,2-c>benz-1,2-oxathiin-2-ol-5,5-dioxide 
• 558644-29-4 4-(5-methyl-1H-pyrazol-3-yl)benzonitrile 
• 132187-08-7 (R)-3-[1-(4-cyanophenyl)-3-oxobutyl]-4-hydroxychromen-2-one 
• 132187-09-8 3-[1-(4-cyanophenyl)-3-oxobutyl]-4-hydroxychromen-2-one 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of 2-(5-methyl-1H-pyrazol-1-yl) acetamide derivatives as androgen receptor antagonists

Androgen receptor (AR) signaling is often activated in prostate cancer (PCa) cells, and blockage of this signaling by AR antagonists is an important strategy in PCa therapy. In this study, we designed and synthesized a series of 2-(5-methyl-1H-pyrazol-1-y

An access to α, β-unsaturated ketones via dual cooperative catalysis

A dual cooperative organocatalytic approach for the synthesis of α, β-unsaturated ketones is described. This one pot transformation is realized via a domino Knoevenagel-Michael-retro Michael reaction sequence. Various aliphatic ketones reacted smoothly with aromatic as well as aliphatic aldehydes in presence catalytic amount of Meldrum's acid and bifunctional amine. The highlights of this protocol are the easy availability of catalysts, high selectivity, and functional group tolerance. The reaction proved to highly E-selective with no side products emanating from self-condensation, unlike the base-mediated reactions.

First aromatic amine organocatalysed activation of α,β-unsaturated ketones

This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a-f) and coumarins (2a-d). The reaction gives rise to warfarin derivatives 3 with promising results using this family of catalysts for the first time. The additional studies performed supported the bifunctional mode of activation of the chiral catalyst VII and the covalent nature of the interactions between the catalyst VII and benzylideneacetones 1.

Discovery of novel 5-methyl-1H-pyrazole derivatives as potential antiprostate cancer agents: Design, synthesis, molecular modeling, and biological evaluation

Androgen receptor (AR) signaling functions as a core driving force for the progression of prostate cancer (PCa), and AR has been proved to be an effective therapeutic target even for castration-resistant prostate cancer (CRPC). Herein, structural modification via a fragments splicing strategy was performed based on two lead compounds T3 and 10e, leading to the discovery of a series of 5-methyl-1H-pyrazole derivatives. AR reporter gene assay revealed compounds A13 and A14 as potent AR antagonists. Some of the compounds in this series inhibited growth of PCa LNCaP cells more efficiently than enzalutamide. A13 and A14 also showed improved metabolic stability compared with 10e in human liver microsomes.

A Mild Procedure for Enone Preparation Catalysed by Bovine Serum Albumin in a Green and Easily Available Medium

Abstract: A simple and mild procedure to obtain α,β-unsaturated ketones from acetone and a set of benzaldehydes is described. The approach applies bovine serum albumin (BSA) catalysis and water or ethanol, this mild reaction medium contrasting with the strong reaction conditions of the classic aldol condensation. Except for the assayed nitrobenzaldehydes, high enone yields (88–97%) were attained. In addition to its mildness, further advantages of this procedure are the use of a green catalyst exhibiting an efficient reuse and the use of eco-friendly and cheap solvents. In order to gain a deeper understanding of the involved catalytic mechanism, computational experiments on BSA structural analysis and molecular docking were carried out.

Enantioselective NiH/Pmrox-Catalyzed 1,2-Reduction of α,β-Unsaturated Ketones

The enantioselective 1,2-reduction of α,β-unsaturated ketones was achieved using a NiH catalyst in the presence of pinacolborane. This mild process represents a general method to access a wide variety of structurally diverse α-chiral allylic alcohols in excellent yields and enantioselectivity, as well as very high levels of ambidoselectivity for 1,2- over 1,4-reduction. Furthermore, for reactions on a 10 mmol scale, catalyst loadings as low as 0.5 mol % could be employed to deliver product without any detrimental effect on the yield, enantio-, or ambidoselectivity.

An efficient transformation of primary halides into nitriles through palladium-catalyzed hydrogen transfer reaction

Two-step one-pot transformation of primary halides into corresponding nitriles is successfully achieved. Nucleophilic substitution of primary halides with sodium azide and subsequent palladium-catalyzed hydrogen transfer proceeds smoothly in the presence of sterically bulky ligand dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) in acetone to produce nitriles in satisfactory to good yields. This journal is

Enantioselective oxidation of secondary alcohols by Candida parapsilosis ATCC 7330

Optically pure allylic alcohols and 4-phenylbutan-2-ols were prepared by oxidative kinetic resolution using whole cells of Candida parapsilosis ATCC 7330. Only the 'S' enantiomer is selectively oxidized to the corresponding keto compound (yield, 37-46%) leaving the 'R' alcohol (yield, 37-52% and ee 46 to >99%). The biocatalytic method is carried out under mild conditions at 20°C, pH 6.5 in phosphate buffer.

PPh3·HBr-DMSO mediated expedient synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters and α-bromo enals: Application to the synthesis of 2-methylsulfanyl-3(2 H)-furanones

An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl 3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described. Copyright

Copper-catalyzed one-pot oxidation-aldol/henry reaction of benzylic amines to α,β-unsaturated methyl ketone/nitro compounds

A novel one-pot synthesis of α,β-unsaturated methyl ketone/nitro compounds from benzylic amines through an oxidation-aldol/Henry reaction is reported. The reaction proceeded well by using MCPBA as oxidant and CuCl 2·2H2O as catalyst. A variety of functionalized α,β-unsaturated methyl ketone/nitro compounds were assembled in moderate yields by application of this catalytic one-pot reaction. Georg Thieme Verlag Stuttgart New York.