79947-88-9

Upstream product

• 402-43-7 p-trifluoromethylphenyl bromide 
• 292638-85-8 acrylic acid methyl ester 
• 98-08-8 α,α,α-trifluorotoluene 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 79-20-9 acetic acid methyl ester 
• 67-56-1 methanol 
• 120681-07-4 3-(4-trifluoromethyl-phenyl)-acryloyl chloride 
• 16642-92-5 4-(trifluoromethyl)cinnamic acid 
• 201230-82-2 carbon monoxide 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 67-48-1 choline chloride 
• 98-56-6 4-chlorobenzotrifluoride 
• 74-88-4 methyl iodide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 125617-18-7 3-(4-trifluoromethylphenyl)-2-propen-1-ol 
• 849442-21-3 methyl 3-(4-(trifluoromethyl)phenyl)propanoate 
• 103977-75-9 p-trifluoromethyl cinnamyl chloride 
• 205108-18-5 (E)-1-(buta-1,3-dien-1-yl)-4-(trifluoromethyl)benzene 
• 95123-61-8 4-(trifluoromethyl)cinnamaldehyde 

Relevant academic research and scientific papers

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

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.

PdII/Novel Chiral Cinchona Alkaloid Oxazoline-Catalyzed Enantioselective Oxidative Cyclization of Aromatic Alkenyl Amides

A highly enantioselective PdII-catalyzed aza-Wacker oxidation tandem cyclization of aromatic nitrogen-containing dienes has been achieved in the presence of novel chiral cinchona alkaloid oxazoline ligands for the first time, affording chiral dihydroindole nitrogen-containing polycyclic compounds with good yields (up to 83 %), high diastereoselectivities (> 95:5 dr), and excellent enantioselectivities (up to 97 % ee).

Synthesis and discovery of 18β-glycyrrhetinic acid derivatives inhibiting cancer stem cell properties in ovarian cancer cells

Despite advances in ovarian cancer treatment, the five-year overall survival rate is less than 30% with the presence of cancer stem cells (CSCs). To develop CSC-targeting therapy, a series of 18β-glycyrrhetinic acid (GA) derivatives containing cinnamamide moiety have been designed, synthesized, and screened for their antiproliferative activity in SKOV3 and OVCAR3 cells. Most of the compounds exhibited stronger antiproliferative activity than GA, and compound 7c was the most active one. Further biological studies showed that compound 7c could induce apoptosis and suppress migration. In addition, compound 7c could not only observably decrease the colony formation and sphere formation ability, but also significantly reduce the CD44+, CD133+, and ALDH+ subpopulation in SKOV3 and OVCAR3 cells. In conclusion, these results indicate that compound 7c is a promising anti-CSC agent for further anti-ovarian cancer studies.

Highly efficient and green esterification of carboxylic acids in deep eutectic solvents without any other additives

A protocol that carboxylic acids esterifies with the quaternary ammonium salt of deep eutectic solvent (DES) is presented, which opens a new access to ester using DES as alkylating agent, solvent, and catalyst. The reaction runs smoothly in DES without any other additives. Substituted cinnamic acids, aromatic acids, and aliphatic acids can be esterified in moderate to good yields. The advantages of this reaction include excellent functional group compatibility and simple reaction procedure.

Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters

A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.

Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst

We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.

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

Synthesis of a cyclometalated 1,3,5-triphenylpyrazole palladium dimer and its activity towards cross coupling reactions

A phosphine free 1,3,5-triphenylpyrazole acetate-bridged palladacycle was prepared from simple commercially available starting materials. The activity of the palladacycle in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions was evaluated. The palladacycle precatalyst shows a wide substrate scope, both in Mizoroki-Heck as well as in Suzuki-Miyaura cross-coupling reactions using low catalyst loadings viz., 0.2 mol% and 0.1 mol% respectively.

Discovery of novel 5,5-diarylpentadienamides as orally available transient receptor potential vanilloid 1 (TRPV1) antagonists

We have developed a novel and potent chemical series of 5,5-diphenylpentadienamides for targeting TRPV1 in vitro and in vivo. In this investigation, we examined a variety of replacements for the 5-position of dienamides with the goal of addressing issues related to pharmacokinetics. Our data suggest that substitution with alkoxy groups on the phenyl ring at the 5-position increases their ability to penetrate the blood-brain barrier. This investigation culminated in the discovery of compound (R)-36b, which showed a good pharmacokinetic profile. In vivo, compound (R)-36b was found to be effective at reversing mechanical allodynia in rats in a dose-dependent manner, and it reversed thermal hyperalgesia in a model of neuropathic pain induced by sciatic nerve injury.