78686-91-6

Upstream product

• 2516-99-6 3,3,3-Trifluoropropionic acid 
• 100-51-6 benzyl alcohol 
• 41463-83-6 3,3,3-trifluoropropanoyl chloride 
• 79594-33-5 benzyltriethylammonium perfluoro-2-methyl-1-ethyl-1-propepenolate 

Downstream Products

• 603039-39-0 C₁₂H₁₃F₃O₃ 
• 1338323-23-1 C₁₇H₁₅F₃O₃ 
• 1374328-83-2 benzyl 2-allyl-2-(trifluoromethyl)pent-4-enoate 
• 787640-48-6 benzyl 3-oxo-1-(trifluoromethyl)cyclopentanecarboxylate 

Relevant academic research and scientific papers

Bis-exo-2-norbornylboron triflate for stereospecific enolization of 3,3,3-trifluoropropionates

The first boron-mediated enolization - aldolization of 3,3,3- trifluoropropionates has been reported. The preparation and application of bis-exo-bicyclo[2.2.1]heptan-2-ylboron triflate as a superior reagent for diastereospecific enolization has also been described.

Three-Component Reactions of α-CF3Carbonyls, NaN3, and Amines for the Synthesis of NH-1,2,3-Triazoles

The development of methods for the assembly of 1,2,3-triazoles is an important topic due to the broad applications of this motif in various scientific fields. In this work, we demonstrate that the three-component assembly of α-CF3 carbonyls, NaN3, and amines was achieved for the selective construction of a variety of 5-amino NH-1,2,3-triazoles under transition-metal-free and open-air conditions. The method provides a general and operationally simple route to functionalized biologically important molecules including carbohydrates, nucleosides, and peptides and exhibits broad substrate scopes. We further demonstrate that the NH-1,2,3-triazoles can be smoothly converted to the regiospecific N-2 alkylated 1,2,3-triazole products. Mechanistic studies based on experiments and density functional theory calculations showed that this transformation proceeds via defluorination-initiated programmed substitution/cyclization/H-transfer to give the 4,5-difunctionalized captodative NH-1,2,3-triazole product.

Formation of α-SF5-enolate enables preparation of 3-SF5-quinolin-2-ones, 3-SF5-Quinolines, and 3-SF5-pyridin-2-ones: Evaluation of their physicochemical properties

This study describes, for the first time, the generation of a SF5-substituted ester enolate from benzyl SF5-acetate under soft enolization conditions, which in turn participates in aldol addition reactions in high yield. The reaction was applied in the synthesis of 3-SF5-quinolin-2-ones, 3-SF5-quinolines, and 3-SF5-pyridin-2-ones, none of which have previously been reported. To provide guidelines for their use in drug discovery, the physicochemical properties of these building blocks were determined and compared with those of their CF3- and t-Bu-analogues.

Synthesis of Small 3-Fluoro- and 3,3-Difluoropyrrolidines Using Azomethine Ylide Chemistry

Here, we report accessing small 3-fluoropyrrolidines and 3,3-difluoropyrrolidines through a 1,3-dipolar cycloaddition with a simple azomethine ylide and a variety of vinyl fluorides and vinyl difluorides. We demonstrate that vinyl fluorides within α,β-unsaturated, styrenyl and even enol ether systems can participate in the cycloaddition reaction. The vinyl fluorides are relatively easy to synthesize through a variety of methods, making the 3-fluoropyrrolidines very accessible.

Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling

The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.

1-(Trifluoromethyl)cyclopent-3-enecarboxylic acid derivatives: Platforms for bifunctional cyclic trifluoromethyl building blocks

We report herein the synthesis and applications of 1-(trifluoromethyl) cyclopent-3-ene-1-carboxylic acid and itsesters, promising new trifluoromethylated cyclic building blocks. Initially prepared starting from a pentafluorodithiopropanoic ester, a more convenient and effective approach has been developed starting from commercially available trifluoropropanoic acid or its methyl ester. The interest in these building blocks is exemplified by their use as platforms for a variety of difunctional trifluoromethylcyclopentane derivatives. We disclose herein a promising new building block, 1-(trifluoromethyl)cyclopent-3-enecarboxylic acid (and its esters), accessible in high yield from commercially available trifluoropropanoic acid derivatives. These building blocks exhibit high synthetic potential, given the reaction diversity offered by the double bond and thecarboxylic function. Copyright

MACROCYCLIC COMPOUNDS USEFUL AS PHARMACEUTICALS

The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of various disorders including inflammatory or autoimmune disorders, and disorders involving malignancy or increased angiogenesis, wherein R1 -R11, t, X, Y, Z, and n are as defined herein.

Reactions of Perfluoro-2-methyl-2-pentene with Carboxylic Acids, Alcohols, and Some Cyclic Amides. A New Fluorinating Reagent

Perfluoro-2-methyl-2-pentene (PMP) reacts with carboxylic acids, alcohols, and 2-pyridone, giving Michael-type addition products, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-acyloxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3-alkoxypentane, 1,1,1,3,4,4,5,5,5-nonafluoro-2-trifluoromethyl-3(2-pyridyloxy)pentane, respectively, in good yields.In the presence of bases, carboxylic acids give acid fluorides, 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-pentanone, and 1,1,1,4,4,5,5,5-octafluoro-2-trifluoromethyl-3-acyloxy-2-pentene (4), the yields changing with base, solvent, phase-transfer catalyst, and their combination.In the presence of triethylamine, fluorination occurs exclusively, producing acid fluorides in good yields.Alcohols and 2-pyridone are converted into alkyl fluorides and 2-fluoropyridine, respectively, with use of triethylamine as a base with an aprotic solvent.The reaction of PMP with 4-pyridone and 6-chloro-2-ethyl-5-methyl-4(3H)-pyrimidone were also examined.The fluorination reactions were rationalized by preferential replacement of the vinylic fluorine of PMP and a good leaving function of the perfluoro enol group of the intermediates such as 4.