115665-96-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Trifluoromethyl-β-nitrostyrene is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Chemical Research:
3-Trifluoromethyl-β-nitrostyrene is used as a research tool in the study of electron-deficient chromenes and styrenes, nitrobenzooxadiazolyl thioethers, and other related compounds. These studies aim to understand the interactions and reactivity of these molecules, which can be crucial for the development of new chemical processes and applications.
Used in Antimicrobial Applications:
3-Trifluoromethyl-β-nitrostyrene is used as a flavodoxin inhibitor in biological studies, with potential applications as an antibacterial agent selective for Helicobacter pylori. This selective targeting could help in the development of more effective treatments for H. pylori infections, which are known to cause various gastrointestinal issues.
Used in Cytotoxicity Testing:
3-Trifluoromethyl-β-nitrostyrene is also used in the evaluation of cytotoxicities, which is essential for assessing the safety and potential side effects of new compounds before they can be considered for therapeutic use. This testing helps ensure that the compounds developed have minimal harmful effects on human cells and tissues.

InChI:InChI=1S/C9H6F3NO2/c10-9(11,12)8-3-1-2-7(6-8)4-5-13(14)15/h1-6H/b5-4+

Upstream product

• 75-52-5 nitromethane 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 2740-83-2 3-(TRIFLUOROMETHYL)BENZYLAMINE 
• 174679-03-9 3-trifluoromethylbenzaldehyde diethyl acetal 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 

Downstream Products

• 1016169-30-4 3-(4-chloro-phenyl)-1-phenyl-4-(3-trifluoromethyl-phenyl)-1H-pyrazole 
• 1186523-50-1 (S)-2-((R)-2-nitro-1-(3-(trifluoromethyl)phenyl)ethyl)cyclohexan-1-one 
• 1262022-87-6 ethyl 2-hydroxy-3-nitro-4-(3-trifluoromethylphenyl)-but-3(E)-enoate 
• 1315313-35-9 diethyl [(3R)-4-nitro-1-oxo-1-phenyl-3-[3-(trifluoromethyl)phenyl]but-2-yl]phosphonate 
• 1329666-66-1 (R)-3-[1-(3-trifluoromethylphenyl)-2-nitroethyl]-1H-indole 
• 1345832-10-1 (1S,2R,4R,E)-tert-butyl 3-(hydroxyimino)-4-(hydroxymethyl)-2'-oxo-2-(3-(trifluoromethyl)phenyl)spiro[cyclopentane-1,3'-indoline]-1'-carboxylate 
• 1370417-72-3 (S)-4-nitro-1-phenyl-3-(3-(trifluoromethyl)phenyl)butan-1-one 
• 1257874-95-5 (S)-5-nitro-4-(3-(trifluoromethyl)phenyl)pentan-2-one 

Relevant academic research and scientific papers

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.

PYRROLIDINONES HERBICIDES

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof: wherein R1, R2, R3, R4, R5, R6, Q1, Q2, Y1, and Y2 /su

Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea

1,3,8-Trihydroxynaphthalene reductase (3HNR) is an essential enzymes that is involved in fungal melanin biosynthesis. Based on the structural informations of active site of 3HNR, a series of β-nitrostyrene compounds were rationally designed and synthesized. The enzymatic activities of these compounds showed that most of them exhibited high inhibitory activities (50 = 0.29 μM). In particular, some of these compounds had moderate fungicidal activity against Magnaporthe grisea. Compound 3-4 showed high in vivo activities against M. grisea (EC50 = 9.5 ppm). Furthermore, compound 3-2 was selected as a representative molecule, and the probable binding mode of this compound and the surrounding residues in the active site of 3HNR was elucidated by using molecular dock. The positive results suggest that β-nitrostyrene derivatives are most likely to be promising leads toward the discovery of novel agent of rice blast.

SUBSTITUTED CYCLIC AMIDES AND THEIR USE AS HERBICIDES

Disclosed are compounds of Formula 1, N-oxides of the compounds and salts of the compounds and N-oxides: wherein R1, R2, R3, R4, R5, R6, Q1, Q2, J, YI and Y

Yolk-shell-structured mesoporous silica: A bifunctional catalyst for nitroaldol-Michael one-pot cascade reaction

Great interest in heterogeneous asymmetric catalysis has focused on obtaining an enantioselective cascade reaction through a controllable active site-isolated heterogeneous catalyst. Herein, we utilize a yolk-shell-structured mesoporous silica and assemble an active site-isolated bifunctional heterogeneous catalyst, where chiral cinchonine-based squaramide molecules are anchored within a silicate channel as an outer shell while amine-functionalities are entrapped onto a silicate yolk as an inner core. Structural analyses and characterizations of the heterogeneous catalyst reveal its well-defined single-site chiral active species within its silicate network. Electron microscopy confirms the yolk-shell-structured mesoporous material. As presented in this study, as a bifunctional heterogeneous catalyst, it enables an efficiently nitroaldol-Michael cascade reaction to conduct the three-component coupling of nitromethane, aldehyde and acetylacetone into various chiral diones with high yields and up to 99% enantioselectivities in a one-pot process. As expected, this active site-isolated catalyst not only enhances the catalytic selectivity of the first-step nitroaldol condensation, but also keeps the enantioselectivity of the second-step Michael addition. Moreover, the heterogeneous catalyst can be also recovered easily and recycled repeatedly, making it an interesting feature in a three-component organic transformation.

PYRROLIDINONES AS HERBICIDES

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof;. whereinRl,R2,R3,R4, R5, R6, Ql, Q2,yl, and Y2are

Copper-catalyzed one-pot oxidation-aldol/henry reaction of benzylic amines to α,β-unsaturated methyl ketone/nitro compounds

A novel one-pot synthesis of α,β-unsaturated methyl ketone/nitro compounds from benzylic amines through an oxidation-aldol/Henry reaction is reported. The reaction proceeded well by using MCPBA as oxidant and CuCl 2·2H2O as catalyst. A variety of functionalized α,β-unsaturated methyl ketone/nitro compounds were assembled in moderate yields by application of this catalytic one-pot reaction. Georg Thieme Verlag Stuttgart New York.

1,4-Conjugate addition of the Reformatsky reagent to α-nitrostyrenes: A new synthesis of γ-nitroesters

α-Nitrostyrenes react with the Reformatsky reagent to yield the corresponding 1,4-addition products. The reaction represents a practical and convenient route to ethyl 3-aryl-4-nitrobutanoates.