96107-02-7

Upstream product

• 367-57-7 1,1,1-Trifluoro-2,4-pentanedione 
• 123-11-5 4-methoxy-benzaldehyde 
• 14774-77-7 p-methoxyphenyllithium 
• 142503-25-1 4-(dimethylamino)-1,1,1-trifluorobut-3-en-2-one 
• 637-69-4 4-Methoxystyrene 
• 407-25-0 trifluoroacetic anhydride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 428842-08-4 (E)-1,1,1-trifluoro-4-morpholinobut-3-en-2-one 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 221915-87-3 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one 
• 243665-13-6 (2E)-N-methoxy-3-(4-methoxyphenyl)-N-methylprop-2-enamide 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 1210825-84-5 2-ethoxy-4-(4-methoxyphenyl)-6-trifluoromethyl-3,4-dihydro-2H-pyran 

Downstream Products

• 251443-11-5 1-(4-aminosulphonylphenyl)-4,5-dihydro-5-(4-methoxyphenyl)-3-trifluoromethyl-1H-pyrazole 
• 1354630-25-3 (Rs,R)-N-((E)-3-hydroxy-5-(4-methoxyphenyl)-1-phenyl-3-(trifluoromethyl)pent-4-enylidene)tert-butanesulfinamide 
• 380905-15-7 5-(4-methoxyphenyl)-3-(trifluoridomethyl)-1H-pyrazole 
• 1537905-30-8 4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-pyran-2-one 

Relevant academic research and scientific papers

Radical Trifluoroacetylation of Alkenes Triggered by a Visible-Light-Promoted C–O Bond Fragmentation of Trifluoroacetic Anhydride

We report a mild and operationally simple trifluoroacylation strategy of olefines, that utilizes trifluoroacetic anhydride as a low-cost and readily available reagent. This light-mediated process is fundamentally different from conventional methodologies and occurs through a trifluoroacyl radical mechanism promoted by a photocatalyst, which triggers a C?O bond fragmentation. Mechanistic studies (kinetic isotope effects, spectroelectrochemistry, optical spectroscopy, theoretical investigations) highlight the evidence of a fleeting CF3CO radical under photoredox conditions. The trifluoroacyl radical can be stabilized under CO atmosphere, delivering the trifluoroacetylation product with higher chemical efficiency. Furthermore, the method can be turned into a trifluoromethylation protocol by simply changing the reaction parameters. Beyond simple alkenes, this method allows for chemo- and regioselective functionalization of small-molecule drugs and common pharmacophores.

SYNTHESIZING METHOD α,β-UNSATURATED KETONE COMPOUND

The present invention relates to a method for preparing an andalpha;,andbeta;-unsaturated ketone compound comprising the step of synthesizing an andalpha;,andbeta;-unsaturated ketone compound represented by Formula 3 below by reacting a styrene compound represented by Formula 1 below with a carboxylic anhydride represented by Formula 2 below. In the Formula 1, R_1 and R_2 are each independently substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted heteroalkyl, and in the Formula 2, A is F, Cl, or F and Cl, and n is 1 to 10.COPYRIGHT KIPO 2021

Catalytic Enantioselective Cloke–Wilson Rearrangement

Racemic cyclopropyl ketones undergo enantioselective rearrangement to deliver the corresponding dihydrofurans in the presence of a chiral phosphoric acid as the catalyst. The reaction involves activation of the donor-acceptor cyclopropane substrate by the

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes - A Short Synthesis of Celebrex (Celecoxib)

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex (celecoxib).

Strong influence of the trifluoromethyl group on the chemoselectivity of [3+2]-cycloadditions of thiocarbonyl S-methanides with α,β-unsaturated ketones

The in situ-generated reactive thiocarbonyl S-methanides were reacted with fluorinated enones. The type of the obtained [3+2]-cycloadduct depends strongly on the location of the activating CF3group. In the case of enones containing the CF3

An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds

A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560.

Highly enantioselective copper(i)-catalyzed conjugate addition of 1,3-diynes to α,β-unsaturated trifluoromethyl ketones

The conjugate diynylation of α,β-unsaturated trifluoromethyl ketones is carried out in the presence of a low catalytic load (2.5 mol%) of a copper(i)-MeOBIPHEP complex, triethylamine and a terminal 1,3-diyne. Pre-metalation of the terminal 1,3-diyne with stoichiometric or higher amounts of dialkylzinc reagent is not required. The corresponding internal diynes bearing a propargylic stereogenic center are obtained with good yields and excellent enantioselectivities. This journal is

Dehydrogenation of perfluoroalkyl ketones by using a recyclable oxoammonium salt

A novel dehydrogenation reaction of perfluoroalkyl ketones by the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+BF4-, Bobbitt's salt, 1) is described. The reaction proceeds under mildly basic conditions and appears to be unique to perfluoroalkyl ketones. A proposed mechanism for this unusual transformation is given. The byproduct of the reaction, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinyloxy (1a), can easily be recovered and used to regenerate the oxoammonium salt. The dehydrogenation of perfluoroalkyl ketones by using an oxoammonium salt is reported. The reaction proceeds under mildly basic conditions and affords α,β-unsaturated products in fair to excellent yields. The reaction likely proceeds through a two-step sequence. The spent oxidant can easily be recovered and used to regenerate the oxoammonium salt. Copyright

A Weinreb amide approach to the synthesis of trifluoromethylketones

A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

A facile synthesis of 4-aryl-1,1,1-trifluorobut-3-en-2-ones via 4-aryl substituted CF3 - containing dihydropyran derivatives: A versatile method for the introduction of fluorine-containing C4- and C6- unit to aromatic compounds

The CF3 - containing dihydropyran derivative (2) reacted easily with various aromatic compounds in trifluoroacetic acid to give novel 4-aryl substituted dihydropyran derivatives (7) in moderate to high yields. Retro hetero Diels-Alder reaction of thus obtained 7 proceeded readily by heating at 300 °C to afford the corresponding 4-aryl-1,1,1-trifluorobut-3-en-2-ones (12) in good to excellent yields. With the use of p-toluenesulfonic acid instead of trifluoroacetic acid together with dihydropyran (2) in acetonitrile, 4-trifluoroacetyl-1,3-butadienylation of 1,3-dimethoxybenzene occurred successfully. The bimolecular reaction of dihydropyran (2) in the presence of p-toluenesulfonic acid was also examined.