76305-00-5

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 101018-39-7 α-ethenyl-α-phenyl-4-methoxybenzenemethanol 
• 2926-29-6 Langlois reagent 
• 611-94-9 4-Methoxybenzophenone 
• 103-80-0 phenylacetyl chloride 
• 100-66-3 methoxybenzene 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 421-06-7 2-bromo-1,1,1-trifluoroethane 

Downstream Products

• 102535-75-1 C₂₄H₂₁F₃O₂ 

Relevant academic research and scientific papers

Cooperative NHC and Photoredox Catalysis for the Synthesis of β-Trifluoromethylated Alkyl Aryl Ketones

Despite the great potential of radical chemistry in organic synthesis, N-heterocyclic carbene (NHC)-catalyzed reactions involving radical intermediates are not well explored. This communication reports the three-component coupling of aroyl fluorides, styrenes and the Langlois reagent (CF3SO2Na) to give various β-trifluoromethylated alkyl aryl ketones with good functional group tolerance in moderate to high yields by cooperative photoredox/NHC catalysis. The alkene acyltrifluoromethylation proceeds via radical/radical cross coupling of ketyl radicals with benzylic C-radicals. The ketyl radicals are generated via SET reduction of in situ formed acylazolium ions whereas the benzylic radicals derive from trifluoromethyl radical addition onto styrenes.

Electrochemical Oxidative Aryl(alkyl)trifluoromethylation of Allyl Alcohols via 1,2-Migration

An electrochemical oxidative difunctionalization of allyl alcohols for the synthesis of β-trifluoromethyl ketones is achieved through a 1,2-migration process. A series of β-trifluoromethyl ketones can be facilely obtained utilizing CF3SO2

Carbotrifluoromethylation of Allylic Alcohols via 1,2-Aryl Migration Promoted by Visible-Light-Induced Photoredox Catalysis

Visible-light-enabled photocatalytic carbotrifluoro-methylations of allylic alcohols and sodium triflinate were explored through 1,2-migration of an aryl group, affording an efficient method for synthesis of β-trifluoromethyl-α-substituted carbonyl compou

Copper-catalyzed trifluoromethylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols

Not only symmetrical, but also unsymmetrical α,α-diaryl allylic alcohols are employed as substrates in the title reaction. A number of arenes and even heteroarenes underwent radical 1,2-aryl migration ("neophyl rearrangement") to produce α-aryl β-trifluoromethyl ketones. The preferential migration of electron-deficient aryl groups over electron-rich ones in unsymmetrical substrates supports the radical mechanism, which was further confirmed by DFT calculations. Copyright

Investigations on estrogen receptor binding. The estrogenic, antiestrogenic, and cytotoxic properties of C2-alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes

C2-Alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes were synthesized and assayed for estrogen receptor binding in a competition experiment with radiolabeled estradiol ([3H]-E2) using calf uterine cytosol. The relative binding affinity decreased with the length of the side chain R = H (3a: 35.2%) > Me (3b: 32.1%) 2CF3 (3d: 5.95%) > n-Pr (3e: 2.09%) > Bu (3f: 0.62%). Agonistic and antagonistic effects were evaluated in the luciferase assay with MCF-7-2a cells stably transfected with the plasmid EREwtcluc. All compounds showed high antiestrogenic activity without significant agonistic potency. The comparison of the IC50 values for the inhibition of E2 (1 nM) documented the dependence of the antagonistic effects on the kind of the side chain: 3a (IC50 = 150 nM), 3b (IC50 = 30 nM), and 3f (IC50 = 500 nM) were weak antagonists, while 3c (IC50 = 15 nM), 3d (IC50 = 9 nM), and 3e (IC50 = 50 nM) were full antiestrogens and antagonized the effect of E2 completely. The most active compound 3d possessed the same antagonistic potency as 4-hydroxytamoxifen (40HT: IC50= 7 nM) without bearing a basic side chain. 3d as well as all other 1,1-bis(4-hydroxyphenyl)-2-phenylalkenes were not able to influence the proliferation of hormone dependent MCF-7 cells despite the antagonistic mode of action. In this assay tamoxifen (TAM) and 40HT reduced the cell growth concentration dependent up to T/Ccorr = 15% and 25%, respectively.