76579-44-7

Usage

Type of compound

Ketone

Structure

Contains a phenyl group substituted with a trifluoroethoxy moiety

Common use

Building block in organic synthesis

Applications

Production of pharmaceuticals and agrochemicals

Reactions

Utilized in nucleophilic additions and substitution reactions

Potential applications

Medicinal chemistry and drug discovery

Ability

To modulate biological activity and potential pharmacological properties

Importance

Versatile and significant compound with various industrial and research applications

Upstream product

• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 100-19-6 (4-nitrophenyl)ethanone 
• 99-90-1 para-bromoacetophenone 
• 99-91-2 para-chloroacetophenone 
• 67-56-1 methanol 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 99-93-4 4-Hydroxyacetophenone 
• 75-89-8 2,2,2-trifluoroethanol 
• 149104-90-5 4-acetylphenylboronic acid 
• 25236-64-0 2,2,2-trifluoroethyl methanesulfonate 

Downstream Products

• 129560-99-2 4-(2,2,2-trifluoroethoxy)phenol 
• 128140-39-6 4'-Pentyl-bicyclohexyl-4-carboxylic acid 4-(2,2,2-trifluoro-ethoxy)-phenyl ester 
• 128140-38-5 4-Pentyl-cyclohexanecarboxylic acid 4-(2,2,2-trifluoro-ethoxy)-phenyl ester 

Relevant academic research and scientific papers

CARBAMATE DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.

Synthesis and evaluation of antiplasmodial activity of 2,2,2-trifluoroethoxychalcones and 2-fluoroethoxy chalcones against plasmodium falciparum in culture

A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group and 2-fluoroethoxy groups were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [3H] hypoxanthine incorporation inhibition assay. Chalcones with 2,2,2-trifluoroethoxy groups substituted on the p- and m-positions of the 1-phenyl ring showed weak antiplasmodial activity, while compounds substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity, thus indicating that 2,2,2-trifluoroethoxy groups on the 1-phenyl ring of chalcones show position-dependent antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively. Moreover, these compounds 3a and 3f showed profound antiplasmodial activity in combination with artemisinin in vitro. The most active molecules, 3a, and 3f, were further assessed for their cytotoxicity towards mammalian Vero cells and the selectivity index (SI) values are 8.6, and 8.2 respectively, being considered non-toxic. We also studied the antiplasmodial activity of 2-fluoroethoxychalcones to discern the effect of the number of fluorine atoms in the fluoroethoxy group. Our results showed that chalcones with 2-fluoroethoxy group on the 1-phenyl ring exhibited more enhanced inhibitory effects on the growth of parasites than their trifluoro analogues, which reveals that monofluoroethoxy group is generally more effective than trifluoroethoxy group in the inhibition of parasite growth. Thus o-2,2,2-trifluoroethoxychalcones (Series 3) and 2-fluoroethoxychalcones may serve as good antiplasmodial candidates for future further development.

Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.

Copper-catalyzed oxidative trifluoroethoxylation of aryl boronic acids with CF3CH2OH

A mild and efficient copper-catalyzed oxidative trifluoroethoxylation of aryl and heteroaryl boronic acids with CF3CH2OH has been developed. This protocol tolerates a range of functional groups, allowing access to a variety of aryl and heteroaryl trifluoroethyl ethers.

Well-defined copper(I) fluoroalkoxide complexes for trifluoroethoxylation of aryl and heteroaryl bromides

Copper(I) fluoroalkoxide complexes bearing dinitrogen ligands were synthesized and the structure and reactivity of the complexes toward trifluoroethoxylation, pentafluoropropoxylation, and tetrafluoropropoxylation of aryl and heteroaryl bromides were investigated. Efficiency drive: A series of copper(I) fluoroalkoxide complexes bearing N,N ligands have been prepared and structurally characterized. These well-defined complexes serve as efficient reagents for the fluoroalkoxylation of aryl and heteroaryl bromides to produce a wide range of trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields.

Transition-Metal-Mediated Synthesis of Trifluoroethyl Aryl Ethers

A series of well-defined copper(I) fluoroalkoxide complexes, [(phen)2Cu][OCH2RF], have been shown to undergo trifluoroethoxylation, pentafluoropropoxylation, and tetrafluoropropoxylation with aryl and heteroaryl bromides to generate the corresponding trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields. The reaction tolerates a variety of functional groups and demonstrates efficient scalability and practicality.

Facile synthesis of trifluoroethyl aryl ethers through copper-catalyzed coupling of CF3CH2OH with aryl- and heteroaryl boronic acids

An efficient copper-catalyzed Chan-Lam reaction of trifluoroethanol with a variety of aryl- and heteroaryl boronic acids has been developed. This research provides a practical method to synthesize trifluoroethyl aryl ethers in moderate to good yields under mild conditions.

Aromatic Fluoroalkoxylation via Direct Displacement of a Nitro or Fluoro Group

Nitro- and fluorobenzenes substituted with a range of electron-withdrawing groups readily undergo fluoroalkoxylation via direct displacement of the nitro or fluoro group.A number of compounds, which cannot be usefully prepared by direct displacement of a chloro group and which are otherwise inaccessible, have been synthesized.Yields and reaction conditions are comparable to those reported by other workers for reactions involving strong nucleophiles.