60710-39-6Relevant articles and documents
Synthesis of Polysubstituted Meta-Halophenols by Anion-Accelerated 2π-Electrocyclic Ring Opening
Staudt, Markus,S?lling, Theis,Bunch, Lennart
supporting information, p. 10941 - 10947 (2021/06/16)
Disrotatory – thermally allowed – 2π-electrocyclic ring-opening reactions require high temperatures to proceed. Herein, we report the first anion-accelerated 2π-electrocyclic ring opening of 6,6-dihalobicyclo[3.1.0]hexan-2-ones at low temperature to give the corresponding meta-halophenols in good to high yields (18 examples, 29–92 % yield, average: 65 %). Many of the phenols have unconventional substitution patterns and are reported here for the first time. Furthermore, the strength of the methodology was shown by the total synthesis of the densely functionalized phenolic natural product caramboxin (isolated as the lactam dehydrate). The reaction mechanism underlying the anion-acceleration was investigated in an ab initio study, which concluded that base-mediated proton abstraction anti to the concurrently departing endo-bromine was the initiating step in an overall concerted reaction mechanism leading directly to the meta-halophenol.
Magnolol dimer-derived fragments as PPARγ-selective probes
Dreier, Dominik,Resetar, Mirta,Temml, Veronika,Rycek, Lukas,Kratena, Nicolas,Schnürch, Michael,Schuster, Daniela,Dirsch, Verena M.,Mihovilovic, Marko D.
, p. 7019 - 7028 (2018/10/17)
Partial agonists of the transcription factor PPARγ (peroxisome proliferator-activated receptor γ) have shown potential for the treatment of metabolic and inflammatory conditions and novel activators serve as valuable tool and lead compounds. Based on the
Explorations of the solubilizing effectiveness of CH3OCH2CH2O substituents in the photocyclizations of some 1,2-diarylethylenes to [n]phenacenes
Bohen, Alyssa A.,Mullane, Kimberly C.,Bohen, Joseph M.,Mallory, Clelia W.,Mallory, Frank B.
, p. 3342 - 3345 (2015/03/18)
We have previously published many photocyclizations of 1,2-diarylethylenes to produce zig-zag aromatic ring systems with n = 5, 7, and 11 fused benzene rings. We invented the name [n]phenacenes for these compounds. To increase their solubilities we attach