104863-67-4

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C4H6F3NO2/c1-8(10-2)3(9)4(5,6)7/h1-2H3

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 217438-93-2 (S)-3-((S)-1-Cyclohexylmethyl-3,3,3-trifluoro-2-oxo-propyl)-4-phenyl-oxazolidin-2-one 
• 1042391-61-6 C₁₅H₁₄F₃NOS 
• 1042391-59-2 C₁₅H₁₄F₃NOS 
• 1135393-67-7 C₁₅H₁₃F₃O₃S 
• 918514-78-0 2-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine 
• 609806-82-8 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one 
• 886370-42-9 2,2,2-trifluoro-1-(6-methoxynaphthalen-2-yl)ethan-1-one 
• 400-31-7 1,1,1-trifluoro-4-methyl-pent-3-en-2-one 
• 85674-68-6 1,1,1-trifluoro-5-phenyl-pentan-2-one 
• 350-92-5 1,1,1-Trifluoro-3-phenylpropan-2-one 
• 1223445-92-8 1-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2,2,2-trifluoroethanone 
• 1800-42-6 2-naphthyl trifluoromethyl ketone 
• 26902-72-7 1,1,1-Trifluorododecan-2-one 
• 174734-34-0 5-methoxy-2-trifluoromethylindole 

Relevant academic research and scientific papers

Economical and practical strategies for synthesis of α-trifluoromethylated amines

A powerful approach to synthesize α-trifluoromethylated amines has been developed. The method is operationally simple, broad in substrate scope and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize α-trifluoromethylated amines but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.

(Z) -Trifluoromethyl-Trisubstituted Alkenes or Isoxazolines: Divergent Pathways from the Same Allene

Because of a charge-dipole interaction involving nonbonding electron pairs on fluorine, protonation of trifluoromethyl allenes leads to tri- or tetrasubstituted alkenes with high (Z)-selectivity. Treatment of the same allenes with catalytic Au(I) initiates a reaction cascade that produces isoxazolines in high yield.

Synthesis, X-ray Structure Determination, and Comprehensive Photochemical Characterization of (Trifluoromethyl)diazirine-Containing TRPML1 Ligands

Potential (trifluoromethyl)diazirine-based TRPML1 ion channel ligands were designed and synthesized, and their structures were determined by single-crystal X-ray diffraction analysis. Photoactivation studies via 19F NMR spectroscopy and HPLC-MS analysis revealed distinct kinetical characteristics in selected solvents and favorable photochemical properties in an aqueous buffer. These photoactivatable TRPML activators represent useful and valuable tools for TRPML photoaffinity labeling combined with mass spectrometry.

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination

The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)3CuF is described. Under the reaction conditions, different trifluoroacetates, trifluoroketones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity

Methuosis is a form of nonapoptotic cell death characterized by an accumulation of macropinosome-derived vacuoles with eventual loss of membrane integrity. Small molecules inducing methuosis could offer significant advantages compared to more traditional anticancer drug therapies that typically rely on apoptosis. Herein we further define the effects of chemical substitutions at the 2-and 5-indolyl positions on our lead compound 3-(5-methoxy-2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propene-1-one (MOMIPP). We have identified a number of compounds that induce methuosis at similar potencies, including an interesting analogue having a hydroxypropyl substituent at the 2-position. In addition, we have discovered that certain substitutions on the 2-indolyl position redirect the mode of cytotoxicity from methuosis to microtubule disruption. This switch in activity is associated with an increase in potency as large as 2 orders of magnitude. These compounds appear to represent a new class of potent microtubule-active anticancer agents.

Identification of highly efficacious glucocorticoid receptor agonists with a potential for reduced clinical bone side effects

Synthesis and structure-activity relationship (SAR) of a series of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain "diazaindole" moieties and display different transcriptional regulatory profiles in vitro and are

Stereoselective transformations of α-trifluoromethylated ketoximes to optically active amines by enzyme-nanometal cocatalysis: Synthesis of (s)-inhibitor of phenylethanolamine n-methyltransferase

One-pot cascade synthesis of optically active α-trifluoromethylated amines directly from ketoximes was accomplished with the use of Candida antarctica lipase B and catalysts prepared by atomic layer deposition (ALD). Compared to the commercial palladium catalyst, the ALD-prepared catalysts showed much higher activity and afforded various α-trifluoromethylated amides in good yields and with high enantioselectivity. One of the enantiopure amides was further hydrolyzed into the corresponding amine, which was treated as a crucial starting material for total synthesis of (S)-inhibitor of phenylethanolamine N-methyltransferase without loss of chiral information.

Chemoenzymatic dynamic kinetic resolution of α-trifluoromethylated amines: Influence of substitutions on the reversed stereoselectivity

Enzymatic resolution of α-trifluoromethylated amines via kinetic resolution (KR), dynamic kinetic resolution (DKR) employing CALB-Pd/Al 2O3, and a one-pot sequential process of KR/DKR/KR was investigated comparatively for the first time. Although CALB-catalyzed KR of α-trifluoromethylated amines with substituents of methyl (1a), isopropyl (1c), phenyl (1d) and benzyl group (1e) can provide good stereoselectivity factors E from 31 to >200 respectively, DKR and sequential process of KR/DKR/KR possess better practical application potential because of the higher conversion (62%-84%) and the similar enantiomeric excesses (90%-99%). The enantiopreference and inversion for the α-trifluoromethylated amines displayed by CALB were observed and explained by docking modes. Namely, for 1,1,1-trifluoro-2-propylamine (1a), the product amide with R-configuration was obtained, and the enantiopreference was converted to S for the amines (1b-1e) with substituents larger than methyl group. The catalysts recycle, and scale-up experiments were demonstrated successfully. All these results indicated the high efficiency and green feature of this enzymatic process, and its application significance.

Nonsteroidal dissociated glucocorticoid agonists containing azaindoles as steroid A-ring mimetics

Syntheses and structure-activity relationships (SAR) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene trans