30934-62-4

Upstream product

• 30993-34-1 2-[(4-trifluoromethyl)benzyl]-1,3-dioxolane 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 32857-62-8 4-Trifluoromethylphenylacetic acid 
• 135325-18-7 methyl 2-(4-(trifluoromethyl)phenyl)acetate 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 721-63-1 (4-trifluoromethylphenyl)acetic acid ethyl ester 
• 1813-97-4 1-allyl-4-(trifluoromethyl)benzene 
• 2968-93-6 2-(4-trifluoromethylphenyl)ethanol 

Downstream Products

• 184360-95-0 (E)-4-((p-trifluoromethyl)phenyl)but-3-enoic acid 
• 187950-48-7 methyl (E)-4-[4-(trifluoromethyl)phenyl]but-3-enoate 
• 187950-52-3 (E)-methyl 2-diazo-4-(4-(trifluoromethyl)phenyl)but-3-enoate 
• 2968-93-6 2-(4-trifluoromethylphenyl)ethanol 
• 1426820-54-3 (4R,5R)-4-hydroxy-5-[4-(trifluoromethyl)phenyl]dihydrofuran-2(3H)-one 
• 1426820-69-0 (4S,5S)-4-hydroxy-5-[4-(trifluoromethyl)phenyl]dihydrofuran-2(3H)-one 
• 1426820-55-4 (3R,4R,5R)-4-hydroxy-5-[4-(trifluoromethyl)phenyl]-3-methyldihydrofuran-2(3H)-one 
• 1426820-57-6 (2S,3S)-2-[(4R,5R)-5-(4-(trifluoromethyl)phenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]hex-5-en-3-ol 
• 590417-82-6 1-[4-(trifluoromethyl)phenyl]propan-2-ol 
• 1065495-75-1 (Z)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine 
• 1065495-55-7 (E)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine 

Relevant academic research and scientific papers

COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY

The present invention relates to chemical entities (for example, a pharmaceutically acceptable compound or salt, and / or a hydrate, and / or a co-crystal, and / or a combination of drug of the compound) which inhibit (for example, antagonize) the stimula

Structure-Activity Relationship Explorations and Discovery of a Potent Antagonist for the Free Fatty Acid Receptor 2

Free fatty acid receptor 2 (FFA2) is a sensor for short-chain fatty acids that has been identified as an interesting potential drug target for treatment of metabolic and inflammatory diseases. Although several ligand series are known for the receptor, the

Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine

The 1,5-benzodiazepines are important skeletons frequently contained in medicinal chemistry. Herein, we described an unexpected tandem cyclization/transfer hydrogenation reaction for obtaining chiral 2,3-disubstituted 1,5-benzodiazepines. The enolizable aryl aldehydes were chosen as substrates to react with symmetric and unsymmetric o-phenylenediamines. The unforeseen tandem reaction occurred among many possible latent side reactions under chiral phosphoric acid catalysis and affords the corresponding products in moderate yields and regioselectivities, good diastereoselectivities, and enantiomeric ratio (up to 99:1).

Manganese and rhenium-catalyzed selective reduction of esters to aldehydes with hydrosilanes

The selective reduction of esters to aldehydes, via the formation of stable alkyl silyl acetals, was, for the first time, achieved with both manganese, -Mn2(CO)10- and rhenium -Re2(CO)10- catalysts in the presence of triethylsilane as reductant. These two methods provide a direct access to a large variety of aliphatic and aromatic alkyl silyl acetals (30 examples) and to the corresponding aldehydes (13 examples) upon hydrolysis. The reactions proceeded in excellent yields and high selectivity at room temperature under photo-irradiation conditions (LED, 365 nm, 40 W, 9 h).

Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding

An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.

α-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease

Increased Gram-negative bacteria resistance to antibiotics is becoming a global problem, and new classes of antibiotics with novel mechanisms of action are required. The caseinolytic protease subunit P (ClpP) is a serine protease conserved among bacteria that is considered as an interesting drug target. ClpP function is involved in protein turnover and homeostasis, stress response, and virulence among other processes. The focus of this study was to identify new inhibitors of Escherichia coli ClpP and to understand their mode of action. A focused library of serine protease inhibitors based on diaryl phosphonate warheads was tested for ClpP inhibition, and a chemical exploration around the hit compounds was conducted. Altogether, 14 new potent inhibitors of E. coli ClpP were identified. Compounds 85 and 92 emerged as most interesting compounds from this study due to their potency and, respectively, to its moderate but consistent antibacterial properties as well as the favorable cytotoxicity profile.

Stereoselective Synthesis of Vinylboronates by Rh-Catalyzed Borylation of Stereoisomeric Mixtures

The stereoselective preparation of vinylboronates via rhodium-catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh-catalyzed borylation-isomerization sequence. The isomerization of (Z)-vinylboronates to (E)-isomers was also demonstrated.

Facile Access to Challenging ortho-Terphenyls via Merging Two Multi-Step Domino Reactions in One-Pot: A Joint Experimental/Theoretical Study

ortho-Terphenyls are of high interest for medicinal chemistry and materials science, but they are difficult to access. Herein, we demonstrate a straightforward and sustainable synthesis of highly functionalized ortho-terphenyls via joining an organocatalyzed two-step domino reaction (Knoevenagel/vinylogous Michael) with a DABCO/CuBr2 co-catalyzed three-step domino reaction (cyclization/tautomerization/aromatization) in a one-pot process. Overcoming necessity to isolate intermediate products leads to a reduction of energy, costs and waste for a broad scope of reactions. DFT calculations have been performed to investigate the thermodynamics of this one-pot process towards ortho-terphenyls and to study the reaction profile of the vinylogous Michael reaction under inclusion of solvent effects. Role of London dispersion forces in this transformation has been elucidated. It is shown that reaction kinetics and thermodynamics are slightly influenced by dispersion interactions. Furthermore, the addition of dispersion energy donors leads to small changes of reaction energies in some cases.

Catalytic Amination of β-(Hetero)arylethyl Ethers by Phosphazene Base t-Bu-P4

We describe the catalytic amination of β-(hetero)arylethyl ethers with amines using the organic superbase t-Bu-P4 to obtain β-(hetero)arylethylamines. The reaction has a broad substrate scope and allows the transformations of electron-deficient and electron-neutral β-(hetero)arylethyl ethers with various amines including pyrrole, N-alkylaniline, diphenylamine, aniline, indole, and indoline derivatives. Mechanistic studies indicate a two-reaction pathway of MeOH elimination from the substrate to form a (hetero)arylalkene followed by the hydroamination of the alkene.

Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols

A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.