51586-24-4

Usage

Uses

Used in Pharmaceutical Industry:
2,2,2-TRIFLUORO-1-PHENYL-ETHYLAMINE serves as a crucial intermediate in the synthesis of a variety of drugs and pharmaceutical products. Its role in this industry is pivotal for the development of new medications and the enhancement of existing ones, contributing to advancements in healthcare and medicine.
Used in Organic Synthesis:
As a reagent, 2,2,2-TRIFLUORO-1-PHENYL-ETHYLAMINE is utilized in organic synthesis processes, facilitating the creation of complex organic molecules and compounds. Its unique properties allow for specific reactions that are otherwise challenging to achieve, thereby expanding the scope of organic chemistry.
Used in Chemical Research:
In the field of chemical research, 2,2,2-TRIFLUORO-1-PHENYL-ETHYLAMINE is employed to explore new chemical reactions, mechanisms, and the development of novel synthetic methodologies. Its application in research aids in uncovering new insights and driving innovation in chemical science.

InChI:InChI=1/C8H8F3N/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5,7H,12H2

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 655-25-4 2,2,2-trifluoroacetophenone oxime 
• 13652-09-0 (RS)-1-phenyl-2,2,2-trifluoroethylamine hydrochloride 
• 134329-15-0 α-Methyl-N-<α-(trifluoromethyl)benzylidene>benzylamine 
• 173668-33-2 N-2,2,2-trifluoro-1-phenylethyl-N-1'-(phenylethyl)amine 
• 53777-08-5 (S)-2-phenyl-butan-2-ol 
• 67655-83-8 2,2,2-trifluoro-1-phenyl-ethanone oxime-O-(4-hydroxyphenylsulfonate) 
• 119561-20-5 N-benzylidene(1-phenyl-2,2,2-trifluoroethyl)amine 
• 119561-19-2 N-(1-phenyl-2,2,2-trifluoroisopropylidene)benzylamine 
• 193202-45-8 2,2,2-Trifluoro-1-phenyl-ethanone O-benzyl-oxime 

Downstream Products

• 1201792-39-3 ethyl (2,2,2-trifluoro-1-phenylethylamino)acetate 
• 1246282-55-2 2,2-ditrifluoromethyl-N-(2,2,2-trifluoro-1-phenylethyl)-propanamide 
• 1429176-15-7 (4S)-4-isopropyl-3-(2-(2,2,2-trifluoro-1-phenylethylamino)pyrimidin-4-yl)oxazolidin-2-one 
• 1589570-35-3 (S)-N-(2,2,2-trifluoro-1-phenylethyl)acetamide 
• 22038-85-3 (R)-(-)-2,2,2-Trifluoro-1-phenylethylamine 
• 61290-83-3 1-(2-Hydroxy-ethyl)-1-methyl-3-(2,2,2-trifluoro-1-phenyl-ethyl)-thiourea 
• 65686-65-9 N-(α-phenyltrifluoroethyl) N'-(β-chloroethyl) Urea 

Relevant academic research and scientific papers

Enantiomeric excess determination of α-amino acids by 19F NMR spectroscopy of their N,N-dimethyl-(2,2,2-trifluoro-1-phenylethyl)amine-C,N)palladium complexes

The synthesis and resolution of the trifluoromethyl-palladacycle, di-μ-chloro-bis(N,N-dimethyl-(2,2,2-trifluoro-1-phenylethyl)amine-2-C,N) palladium(II) are shown. The utility of the complex and its application in the enantiomeric excess determination of α-amino acids by 19F NMR spectroscopy is demonstrated and X-ray diffraction analysis of one of the diastereomeric complexes, trans-{[(R)-phenylglycinato-N,O][(R)-N,N-dimethyl-(2,2,2-trifluoro-1- phenylethyl)amine-C,N]palladium(II)}, is reported.

Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R

Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.

Discovery of N-Cyano-sulfoximineurea Derivatives as Potent and Orally Bioavailable NLRP3 Inflammasome Inhibitors

NLRP3 inflammasome mediated release of interleukin-1β (IL-1β) has been implicated in various diseases. In this study, rationally designed mimics of sulfonylurea moiety were investigated as NLRP3 inhibitors. Our results culminated into discovery of series of unprecedented N-cyano sulfoximineurea derivatives as potent NLRP3 inflammasome inhibitors. Compound 15 (IC50 = 7 nM) and analogues were found to be highly potent and selective NLRP3 inflammasome inhibitor with good pharmacokinetic profile. These effects translate in vivo, as 15, 29, and 34 significantly inhibit NLRP3 dependent IL-1β secretion in mice.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

IDO inhibitors

The invention discloses novel compounds used as indoleeamine-pyrrole-2,3-dioxygenase (IDO) inhibitors, and specifically discloses the compounds represented by a formula (I) shown in the description and pharmaceutically-acceptable salts of the compounds. The invention also discloses an application of the compounds represented by the formula (I) and the pharmaceutically-acceptable salts of the compounds in preparation of a medicament for treating tumors.

Silver-catalyzed formal [3+2]-cycloaddition of α-trifluoromethylated methyl isocyanides: a facile stereoselective synthesis of CF3-substituted heterocycles

An Ag-catalyzed formal [3+2]-cycloaddition of α-trifluoromethylated methyl isocyanides with polar double bonds has been developed for the facile access to trifluoromethylated oxazolines, imidazolines and pyrrolines under mild conditions. The practicality of this chemistry is demonstrated by the gram-scale synthesis of oxazolines with excellent yields and facile transformations of the formed oxazolines to trifluoromethylated β-amino alcohols in quantitative yields.

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.

Structure-activity study leading to identification of a highly active thienopyrimidine based EGFR inhibitor

Based on the thieno[2,3-d]pyrimidine scaffold, a series of new 4-amino-6-aryl thienopyrimidines have been prepared and evaluated as EGFR tyrosine kinase inhibitors. The in vitro activity was found to depend strongly on the substitution pattern in the 6-aryl ring, the stereochemistry, and the basicity at the secondary 4-amino group. A stepwise optimization by combination of active fragments led to the discovery of three structures with EGFR IC 50 50 of 0.3 nM towards EGFR and its mutants L858R and L861Q. Studies using human cancer cell lines and an EGFR-L858R reporter cell system revealed good cellular potency, verifying the identified thienopyrimidines as promising lead structures.

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.