642941-68-2

Usage

Chemical compound

2-Propenamide, 3-(4-fluorophenyl)-(9CI)

Uses

Research, potential pharmaceutical and industrial applications

Handling

Care must be taken as it can have toxic effects if not used properly
Varied properties and uses depending on context and intended application

Upstream product

• 1262991-68-3 tert-butyl 2-(4-fluorophenyl)diazene-1-carboxylate 
• 1589517-78-1 tetra-n-butylammonium 4-fluorophenylazocarboxylate 
• 79-06-1 2-propenamide 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 201230-82-2 carbon monoxide 
• 930769-46-3 (+/-)-4-(4-fluorophenyl)-2-azetidinone 
• 71-43-2 benzene 
• 459-32-5 4-fluorocinnamic acid 
• 13565-08-7 4-fluorocinnamoyl chloride 

Downstream Products

• 1361194-37-7 3,3-bis(4-fluorophenyl)acrylamide 
• 101488-65-7 3-(4-fluorophenyl)propan-1-amine 

Relevant academic research and scientific papers

Design, Synthesis, and Structure-Activity Relationship Studies of Dual Inhibitors of Soluble Epoxide Hydrolase and 5-Lipoxygenase

Inhibition of multiple enzymes of the arachidonic acid cascade leads to synergistic anti-inflammatory effects. Merging of 5-lipoxygenase (5-LOX) and soluble epoxide hydrolase (sEH) pharmacophores led to the discovery of a dual 5-LOX/sEH inhibitor, which was subsequently optimized in terms of potency toward both targets and metabolic stability. The optimized lead structure displayed cellular activity in human polymorphonuclear leukocytes, oral bioavailability, and target engagement in vivo and demonstrated profound anti-inflammatory and anti-fibrotic efficiency in a kidney injury model caused by unilateral ureteral obstruction in mice. These results pave the way for investigating the therapeutic potential of dual 5-LOX/sEH inhibitors in other inflammation- and fibrosis-related disease models.

Palladium-Catalyzed Regioselective Hydroaminocarbonylation of Alkynes to α,β-Unsaturated Primary Amides with Ammonium Chloride

α,β-Unsaturated primary amides have found numerous applications in drug development, organic materials, and polymer sciences. However, the catalytic synthesis of α,β-unsaturated primary amides via carbonylation of alkynes has long been an elusive endeavor. Here, we report a novel palladium-catalyzed hydroaminocarbonylation of alkynes with NH4Cl as the amine source, enabling the highly chemo- and regioselective synthesis of α,β-unsaturated primary amides. A variety of alkynes, including aromatic alkynes, aliphatic alkynes, terminal alkynes, internal alkynes, as well as diynes with various functional groups, react well. The method turns the parasitic noncoordination ability of ammonium salts into a strategic advantage, enabling the gram-scale reaction to be performed in the presence of 0.05 mol % of catalyst with excellent selectivity.

Hydrogen Peroxide Promoted Mizoroki-Heck Reactions of Phenyldiazenes with Acrylates, Acrylamides, and Styrenes

Mizoroki-Heck reactions, which are well-known for aryldiazonium salts and which have recently been described for arylhydrazines, have now been extended to phenyldiazenes. In situ generation of phenyldiazenes from azocarboxylates allowed clean and selective reactions with styrenes, acrylates, and acrylamides using palladium(II) acetate in the presence of silver(I) acetate or hydrogen peroxide as oxidant. Hydrogen peroxide was thereby shown to be a cheap and broadly applicable alternative for the established palladium-silver(I) system.

The acid-mediated ring opening reactions of α-aryl-lactams

4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl ex

Synthesis, structure and quantitative structure-activity relationships of σ receptor ligands, 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazines

A set of the title compounds having different substituents (R1, R2) on their phenyl groups was synthesized to find σ receptor binding affinity. Among the compounds, 2b (R1=R2=Cl) has the most potent σ1-binding activity, while 2a (R1=R2=H, SA4503) was most selective to σ1 over σ2 receptor. The crystal structures of 2a and 2b were shown, by X-ray crystallography, to be similar except for the one torsional angle of their propylene parts. Quantitative structure-activity relationship study suggested the affinity of the compounds to the σ1 receptor was dependent on the electronic feature, Swain-Lupton's R or S(π) that was derived by molecular orbital method, of R1 and R2.