85674-68-6

Upstream product

• 126526-19-0 phenethyl-2 trifluoroacetylacetate d'ethyle 
• 100-42-5 styrene 
• 421-50-1 1,1,1-trifluoro-2-propanone 
• 112298-06-3 5-phenyl-1,1,1-trifluoropentan-2-ol 
• 18496-54-3 phenylbutyric acid chloride 
• 407-25-0 trifluoroacetic anhydride 
• 122983-05-5 1,1,1-trifluoro-5-phenylpentan-2-amine 
• 637-59-2 1-Bromo-3-phenylpropane 
• 4119-41-9 1-iodo-3-phenylpropan 
• 17376-04-4 2-phenethyl iodide 
• 383-63-1 ethyl trifluoroacetate, 
• 104863-67-4 N-methoxy-N-methyltrifluoroacetamide 
• 186001-41-2 4-((E)-4-Phenyl-1-trifluoromethyl-but-1-enyl)-morpholine 
• 1821-12-1 4-Phenylbutyric acid 

Downstream Products

• 112298-38-1 1-(p-methoxyphenyl)-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalene 
• 112298-21-2 2-(p-chlorophenyl)-5-phenyl-1,1,1-trifluoropentan-2-ol 
• 112481-87-5 1-p-Tolyl-1-trifluoromethyl-1,2,3,4-tetrahydro-naphthalene 
• 112298-22-3 2-(m-chlorophenyl)-5-phenyl-1,1,1-trifluoropentane-2-ol 
• 112481-80-8 1-chloro-1-trifluoromethyl-tetralin 
• 112298-33-6 1-phenyl-1-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalene 
• 112298-41-6 (4-(trifluoromethyl)pent-4-en-1-yl)benzene 
• 641618-99-7 C₁₁H₁₁F₃ 
• 1452406-25-5 1,1-difluoro-5-phenylpentan-2-one 

Relevant academic research and scientific papers

Efficient Asymmetric Biomimetic Aldol Reaction of Glycinates and Trifluoromethyl Ketones by Carbonyl Catalysis

The direct asymmetric aldol reaction of glycinates represents an intriguing and straightforward strategy to make biologically significant chiral β-hydroxy-α-amino-acid derivatives. But it is not easy to realize the transformation due to the disruption of the reactive NH2 group of glycinates. Inspired by the enzymatic aldol reaction of glycine, we successfully developed an asymmetric aldol reaction of glycinate 5 and trifluoromethyl ketones 4 with 0.1–0.0033 mol % of chiral N-methyl pyridoxal 7 a as the catalyst, producing chiral β-trifluoromethyl-β-hydroxy-α-amino-acid esters 6 in 55–82 % yields (for the syn-diastereomers) with up to >20:1 dr and 99 % ee under very mild conditions. The reaction proceeds via a catalytic cycle similar to the enzymatic aldol reaction of glycine. Pyridoxal catalyst 7 a activates both reactants at the same time and brings them together in a specific spatial orientation, accounting for the high efficiency as well as excellent diastereo- and enantioselectivities.

Radical C(sp2)-H Trifluoromethylation of Aldehydes in Aqueous Solution

The copper-mediated C(sp2)-H trifluoromethylation of aldehydes is described. The reaction of aldehydes with (bpy)Cu(CF3)3, Et3SiH, and K2S2O8 in aqueous acetone at room temperatu

Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics

Described is a facile, scalable route to access functional-group-rich gem-difluoroalkenes. Using visible-light-activated catalysts in conjunction with an arsenal of carbon-radical precursors, an array of trifluoromethyl-substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two-electron pathways. The process readily extends to other perfluoroalkyl-substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl-substituted alkene starting materials.

High-Pressure-Mediated Asymmetric Organocatalytic Hydroxyalkylation of Indoles with Trifluoromethyl Ketones

An enantioselective hydroxyalkylation of indoles and 7-azaindole with trifluoromethyl ketones was found to be effectively promoted under high-pressure conditions with a low loading of Cinchona alkaloids (e.g., 1–3 mol% of cinchonidine). Chiral tertiary alcohols containing a trifluoromethyl group were obtained at 9 kbar with good yield and enantioselectivity up to 89%, whereas usually merely traces of products were detected at atmospheric pressure. (Figure presented.).

The effect of various zinc binding groups on inhibition of histone deacetylases 1-11

Histone deacetylases (HDACs) have the ability to cleave the acetyl groups of ε-N-acetylated lysine residues in a variety of proteins. Given that human cells contain thousands of different acetylated lysine residues, HDACS may regulate a wide variety of processes including some implicated in conditions such as cancer and neurodegenerative disorders. Herein we report the synthesis and ina vitro biochemical profiling of a series of compounds, including known inhibitors as well as novel chemotypes, that incorporate putative new zinc binding domains. By evaluating the compound collection against all 11 recombinant human HDACs, we found that the trifluoromethyl ketone functionality provides potent inhibition of all four subclasses of the Zn2+- dependent HDACs. Potent inhibition was observed with two different scaffolds, demonstrating the efficiency of the trifluoromethyl ketone moiety as a zinc binding motif. Interestingly, we also identified silanediol as a zinc binding group with potential for future development of non-hydroxamate classa I and classa IIb HDAC inhibitors.

New methodology toward α,β-unsaturated carboxylic acids from saturated acids

A carefully designed three-step unsaturation of carboxylic acids is described. Briefly, carboxylic acids were converted to the trifluoromethyl ketone. Subsequent treatment with selenium dioxide followed by hydrolysis afforded α,β-unsaturated carboxylic acids. The mechanism of the reported transformation was investigated, which led us to propose a novel explanation featuring selenium dioxide assisted enolizaion of a trifluoromethyl ketone followed by β-deprotonation.

MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY

Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.

FATTY ACID AMIDE HYDROLASE INHIBITORS

Disclosed are compounds of formula R-X-Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CBl and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.

A new, practical and efficient sulfone-mediated synthesis of trifluoromethyl ketones from alkyl and alkenyl bromides

We report herein a new and efficient method to prepare trifluoromethyl ketones from the corresponding bromides through sulfones in good yields.

Radical-mediated synthesis of trifluoroethyl amines and trifluoromethyl ketones from alkyl iodides

Radical reaction of alkyl iodides with trifluoromethyl phenylsulfonyl oxime ether 10 and hexamethylditin at 300 nm in benzene afforded the corresponding trifluoromethyl oxime ethers 11 in high yields, which were reduced into the 2,2,2-trifluoroethyl amines with lithium aluminium hydride. The trifluoroethyl amines could be converted into the corresponding trifluoromethyl ketones by treatment with NBS and DBU.