52116-81-1

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-CYANO-PHENYL)-ACRYLIC ACID METHYL ESTER is used as a reagent for the synthesis and evaluation of analogous diisopropylpyridine acetamides. These acetamides are potent antagonists of the Kv1.5 potassium channel, which plays a crucial role in the regulation of cardiac and smooth muscle cell excitability. By targeting this channel, these antagonists have potential therapeutic applications in the treatment of atrial fibrillation and other cardiovascular diseases.
Used in Chemical Synthesis:
In the field of organic chemistry, 3-(3-CYANO-PHENYL)-ACRYLIC ACID METHYL ESTER can be utilized as a building block for the synthesis of various complex molecules. Its reactive sites, such as the cyano group and the ester functionality, can be further modified to create a wide range of compounds with diverse properties and applications.
Used in Material Science:
The unique structure of 3-(3-CYANO-PHENYL)-ACRYLIC ACID METHYL ESTER may also find applications in the development of new materials with specific properties. For instance, its incorporation into polymers could lead to materials with enhanced mechanical strength, thermal stability, or electrical conductivity, depending on the desired application.

InChI:InChI=1/C11H9NO2/c1-14-11(13)6-5-9-3-2-4-10(7-9)8-12/h2-7H,1H3/b6-5+

Upstream product

• 24964-64-5 3-Cyanobenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 6952-59-6 3-cyanobromobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 16642-93-6 (3E)-3-(3-cyanophenyl)acrylic acid 
• 107-06-2 1,2-dichloro-ethane 
• 186581-53-3 diazomethane 
• 32858-79-0 3-cyanocinnamic acid 

Downstream Products

• 193151-11-0 3-(3-cyano-phenyl)-propionic acid methyl ester 
• 325798-09-2 methyl 3-(3-aminomethylphenyl)propionate hydroacetate 
• 193151-12-1 3-(3-cyanophenyl)propionic acid thiopyridyl ester 
• 202208-74-0 3-(3-Cyano-phenyl)-propionyl chloride 
• 42287-97-8 3-(3-cyanophenyl)propanoic acid 

Relevant academic research and scientific papers

Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis

Direct α-functionalization of NH2-free glycinates with relatively weak electrophiles such as α,β-unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α-C of glycinate 1 a with α,β-unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 % yields with 81–97 % ee's after in situ lactamization. The trans and cis diastereomers can be obtained at the same time by chromatography and both of them can be easily converted into chiral 4-substituted pyrrolidin-2-ones such as Alzheimer's drug Rolipram (11) with the same absolute configuration via tert-butyl group removal and subsequent Barton decarboxylation.

Flexible, dicationic imidazolium salts for in situ application in palladium-catalysed Mizoroki–Heck coupling of acrylates under aerobic conditions

The synthesis, characterization and in situ catalytic performance of new unsymmetric N,N′-disubstituted imidazolium-based dicationic salts in Mizoroki–Heck coupling of acrylates with aryl bromides under aerobic conditions are described. A series of flexible dicationic salts with varying steric and electronic properties were synthesized in good to excellent yields. All the salts were well characterized using spectroscopic techniques. X-ray diffraction analysis of two salts with the same dicationic backbone and different counter anions shows that the ligand adopts two different conformations which are influenced by the nature of the anion. Thus, the ligand is capable of changing its conformation according to the change in environment due to its flexible nature. All the synthesized imidazolium salts were found to be active in in situ palladium-catalysed Mizoroki–Heck coupling under aerobic conditions. Amongst the salts, the hydroxyl-functionalized imidazolium salt, incorporating the features of both bidentate chelating O,O ligand and carbene, shows the maximum catalytic activity. A variety of aryl and heteroaryl methyl and ethyl cinnamates were synthesized using these imidazolium salts as preligands. In addition, NMR studies confirm in situ generation of normal N-heterocyclic carbenes from the C-2 position of imidazol-2-ylidene ring. The mercury poisoning test was also performed to ascertain the nature of catalytically active palladium species. Aerobic conditions, low catalytic loading (0.5?mol%), shorter reaction times, broad functional group tolerance and good to excellent isolated yields are some of the significant features of the novel catalytic systems described here. Copyright

A robust first-pass protocol for the heck-mizoroki reaction

The Heck-Mizoroki (HM) reaction is one of the most widely used C-C bond-forming methods of contemporary synthesis. Notwithstanding this, these reactions frequently require significant optimization before efficient transformations can be obtained. We describe here the results of a study that aimed to establish a generic experimental protocol for HM reactions which enables acceptable yields from first-pass experiments. The methodology utilizes readily available stable catalysts and can be applied to a broad range of coupling partners.

Inhibitors of factor Xa

Novel compounds, their salts and compositions related thereto having activity against mammalian factor Xa are disclosed. The compounds are useful in vitro or in vivo for preventing or treating coagulation disorders.

Identification and initial structure-activity relationships of a novel class of nonpeptide inhibitors of blood coagulation factor Xa

The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized β-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted β-alanines was also developed.

Aromatic compounds substituted by 4,6-bis(trichloromethyl)-s-triazin-2-yl groups

Compounds of general formula STR1 are disclosed in which R1 and R2 are different from one another and denote either a hydrogen atom or a radical of the formula STR2 R3 denotes a substituted or unsubstituted alkoxy, alkenyloxy, alkynyloxy or aryloxy radical, a hydroxyl group or a halogen atom and n the number 0 or 1. The compounds are useful intermediates for the preparation of photoinitiators and are themselves active as photoinitiators.