115665-92-4

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 67-64-1 acetone 
• 1384879-87-1 (E)-methyl 3-oxo-3-[2-(4-trifluoromethylstyryl)phenyl]propanoate 
• 78-94-4 methyl vinyl ketone 
• 113170-92-6 1-(but-3-en-1-yl)-4-(trifluoromethyl)benzene 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 598-32-3 2-hydroxy-3-butene 
• 98-56-6 4-chlorobenzotrifluoride 
• 128796-39-4 4-trifluoromethylphenylboronic acid 

Downstream Products

• 251443-23-9 4,5-Dihydro-3-methyl-1-(4-methylsulphonylphenyl)-5-(4-trifluoromethylphenyl)-1H-pyrazol 
• 1004987-41-0 1-[(1S,2R,3R,4R)-3-(4-trifluoromethylphenyl)bicyclo[2.2.1]hept-5-en-2-yl]ethanone 
• 944805-39-4 (S,E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-ol 
• 1056017-61-8 diethyl 2-((S)-1-(4-(trifluoromethyl)phenyl)-3-oxobutyl)malonate 
• 1199945-10-2 (E)-(1-(p-trifluoromethyl)phenyl)-3-methyl-1,5-hexadien-3-ol 
• 1245720-67-5 (R,E)-4-(4-(trifluoromethyl)phenyl)but-3-en-2-ol 

Relevant academic research and scientific papers

The effect of acid-base pairing on catalysis: An efficient acid-base functionalized catalyst for aldol condensation

Acid-base bifunctionalized heterogeneous catalysts may be capable of exhibiting reactivity not achievable with homogeneous catalysts. We investigated the effect of pKa of the acid component of mesoporous solids containing acid-base bifunctionality on their catalytic ability toward aldol condensation between 4-nitrobenzaldehyde and acetone. We found that higher levels of aldol product conversion were obtained when weaker acid components (phosphoric, carboxylic vs sulfonic) were used, an indication of the importance of the equilibrium between free acid and free base and the resulting neutralized ion pair in the catalytic capability of acid-base functionalized materials. A catalyst containing primary amine groups in combination with carboxylic acid groups (with similar chemical functionalities to proline) was found to be a superior catalyst in this aldol reaction with a number of different electrophilic components.

N-vinylpyridinium and -ammonium tetrafluoroborate salts: New electrophilic coupling partners for Pd(0)-catalyzed suzuki cross-coupling reactions

N-Vinylpyridinium and -trialkylammonium tetrafluoroborate salts represent a new class of electrophilic coupling partner for Pd(0)-catalyzed Suzuki cross-coupling reactions and give very good to excellent yields of products with a wide range of boronic acids. The salts are easily prepared from activated acetylenes and pyridinium or trialkylammonium tetrafluoroborates to form crystalline, air-stable, and nonhygroscopic crystals.

Synthesis of new 4-phenylpyrimidine-2(1H)-thiones and their potency to inhibit COX-1 and COX-2

Several new 4-phenylpyrimidine-2(1H)-thiones have been prepared and investigated for their potencies to inhibit COX-1 and COX-2 enzymes, and COX-2 expression in THP-1 cells. Structure-activity-relationships and physicochemical parameters are discussed. Pharmacophore screening and docking studies were carried out for the most active compound.

Piperlongumine derivative as well as preparation method and application thereof

The invention discloses a Piperlongumine derivative as well as a preparation method and application thereof. The Piperlongumine derivative has the following structure: the Piperlongumine derivative provided by the invention contains a plurality of Michael addition receptor units, and the novel structure improves the electrophilicity, so that the Piperlongumine derivative has good protein targetingpotential, and the Piperlongumine derivative has a good inhibition effect on thioredoxin reductase; in an antitumor bioactive in-vitro screening experiment, the derivative also has a certain inhibition effect on the growth of tumor cells, and meanwhile, the derivative has an effect of promoting the generation of active oxygen in A549 human lung cancer cells.

Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction

The present report describes an organocatalytic cascade reaction between 2-alkylidene benzo[b]thiophenone derivatives and enones in the presence of the Cinchona alkaloid amine. Spirobenzothiophenonic cyclohexane derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines

The Pd-catalyzed cross-coupling reactions of Sb-aryl-1,5-azastibocines with alkenes are described. The reactions of azastibocines with alkenes such as vinyl ketones, alkenes, and acrylates in the presence of 10 mol% PdCl2 at 80 °C in DMA under aerobic conditions produced Heck adducts in moderate-to-excellent yields. Single-crystal X-ray and NMR analysis revealed that the aryl donors in this reaction, the Sb-aryl-1,5-azastibocines, are hypervalent compounds that display N–Sb intramolecular non-bonding interaction. These are the first examples of Pd-catalyzed Heck-type arylations using heterocyclic hypervalent organoantimony compounds. Although the reactions proceeded efficiently with the azastibocines, they hardly progressed with trivalent and pentavalent triarylantimony reagents.

Catalytic Enantioselective Conjugate Addition of Stereodefined Di- and Trisubstituted Alkenylaluminum Compounds to Acyclic Enones

Catalytic enantioselective conjugate addition (ECA) reactions with readily accessible and stereochemically defined E-, Z-, di- and trisubstituted alkenyl aluminum compounds are disclosed. Transformations are promoted by various NHC-copper catalysts (NHC=N-heterocyclic carbene), which are derived from enantiomerically pure sulfonate imidazolinium salts. The desired products were obtained in up to 89% yield and >99:1 e.r.; the alkenyl moiety was transferred with complete retention of its stereochemical identity in all instances. The scope and limitations of the approach, key mechanistic attributes, and representative functionalization are presented as well. (Figure presented.).

New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling

In this work, a serie of cyclocoumarol derivatives was designed, synthesized, characterized and studied for their potentialities as selective inhibitors of COX-2. All target compounds have been screened for their anti-inflammatory activity by the assay of PGE2 production. Among them, compound 5d exhibited the most potent inhibitory activity with a PGE2 inhibition compared to NS-398 (79% and 88% respectively) and showed non-inhibitory activity towards the COX-1 enzyme. Docking studies revealed the capacity of this compound to occupy the selective COX-2 cavity establishing additional hydrogen bonds between the oxygen of the methoxy group and the His90 and Arg513 of the binding site of the enzyme.

Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones

Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.

Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: Chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles

A copper-catalyzed transfer aldol type reaction of β-hydroxy ketones or nitriles with aldehydes is reported, which enables chemo- and stereoselective access to (E)-α,β-unsaturated ketones and (E)-acrylonitriles. A key step of the in situ copper(i)-promoted retro-aldol reaction of β-hydroxy ketones or nitriles is proposed to generate a reactive Cu(i) enolate or cyanomethyl intermediate, which undergoes ensuing aldol condensation with aldehydes to deliver the products. This reaction uses 1.2 mol% Cu(IPr)Cl (IPr denotes 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) as the catalyst in the presence of 6.0 mol% NaOtBu cocatalyst at room temperature or 70 °C. A range of aryl and heteroaryl aldehydes as well as acrylaldehydes are compatible with many useful functional groups being tolerated. Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine in excellent yields (up to 91%). Finally, a full catalytic cycle for this reaction has been constructed using DFT computational studies in the context of a retro-aldol/aldol two-stage mechanism. A rather flat reaction energy profile is found indicating that both stages are kinetically facile, which is consistent with the mild reaction conditions.