409359-86-0

Upstream product

• 5459-35-8 2-bromo-acrylic acid ethyl ester 
• 3058-39-7 4-iodobenzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 6111-99-5 ethyl diazoalaninate 
• 50-00-0 formaldehyd 
• 1528-41-2 ethyl 4-cyanophenylacetate 

Downstream Products

• 934476-99-0 3-acetylsulfanyl-2-(4-cyano-phenyl)-propionic acid 
• 1264519-79-0 (S)-3-tert-butyl 1-(phenanthren-9-yl) 1-(4-cyanophenyl)cyclopent-3-ene-1,3-dicarboxylate 
• 1264519-10-9 phenanthren-9-yl 2-(4-cyanophenyl)acrylate 
• 934476-97-8 2-(4-cyanophenyl)acrylic acid 

Relevant academic research and scientific papers

Enantioselective Enzymatic Reduction of Acrylic Acids

An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- A nd aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).

Overcoming Scope Limitations in Cross-Coupling of Diazo Nucleophiles by Manipulating Catalyst Speciation and Using Flow Diazo Generation

The accessible scope of palladium-catalyzed diazo cross-coupling reactions has been expanded to include aryl chlorides by controlled diazo slow addition. The success of this strategy is based on manipulating speciation within the catalytic cycle through starvation of the diazo reagent to make the Pd(II) oxidative intermediate the resting state. The strategy is also applicable to cross-coupling reactions with aryl bromides and, in combination with safe, on-demand flow generation of nonstabilized diazo reagents, has been used to greatly expand the scope of applicable diazo compounds for this chemistry as well. Lastly, DFT calculations have provided insight into the mechanism and support for the proposed explanation for success of the slow addition strategy.

3-Mercaptopropionic acids as efficacious inhibitors of activated thrombin activatable fibrinolysis inhibitor (TAFIa)

A novel series of cyclic potent, selective, small molecule, thiol-based inhibitors of activated thrombin activatable fibrinolysis inhibitor (TAFIa) and the crystal structures of TAFIa inhibitors bound to porcine pancreatic carboxypeptidase B are described. Three series of cyclic arginine and lysine mimetic inhibitors vary significantly in their selectivity against other human basic carboxypeptidases, carboxypeptidase N and carboxypeptidase B. (-)2a displays TAFIa IC50 = 3 nM and 600-fold selectivity against CPN. Inhibition of TAFIa with (rac)2a resulted in dose dependent acceleration of human plasma clot lysis in vitro and was efficacious as an adjunct to tPA in an in vivo rabbit jugular vein thrombolysis model.

Facile synthesis of ethyl 2-arylpropenoates by cross-coupling reaction using electrogenerated highly reactive zinc

Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. This reactive zinc was used for efficient transformation of ethyl 2-bromoacrylate into the corresponding organozinc compound, which was reacted with various aryl iodides or bromides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 to give the corresponding cross-coupling products in high yields. These cross-coupling reactions were successfully applied to a synthesis of the precursor of naproxen and cicloprofen, non-steroidal anti-inflammatory agent.

Facile synthesis of 2-arylpropenoic acid esters by cross-coupling using electrogenerated highly reactive zinc and a palladium catalyst

Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. The reaction of this reactive zinc with ethyl 2-bromoacrylate at -20 °C and the following cross-coupling reaction with aryl iodides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 at 70 °C gave the corresponding ethyl 2-arylpropenoates in almost quantitative yields.