62224-33-3Relevant academic research and scientific papers
Development of the radical C–O coupling reaction of phenols toward the synthesis of natural products comprising a diaryl ether skeleton
Tanaka, Kumpei,Gotoh, Hiroaki
, p. 3875 - 3885 (2019/06/18)
Compounds comprising a diaryl ether skeleton exist among natural phenols. The diaryl ether skeleton is thought to be biosynthesized through the coupling of two or more phenols. It is an important structural feature in medicines and agrochemicals, and it is imperative to develop methods for constructing such skeletons in organic synthesis. However, by the synthesis method through the coupling of phenols, coupling occurs preferentially at the ortho-substituted carbon atom of phenols. In this study, various radical-generating reagents and conditions were investigated with the aim of developing a short-step construction method of the diaryl ether skeleton by the radical homo-coupling of two phenol molecules. In addition, cross-coupling reactions between radicals of 2,4,6-tri-tert-butylphenol and p-substituted phenol were conducted to synthesize eight C (ortho)–O coupling products. Based on the results, a computational chemical approach was employed to verify the cause of C (ortho)–O bond formation.
Enzymatic oxidative polymerization of p-t-butylphenol and characterization of the product polymer
Mita, Naruyoshi,Maruichi, Naoyuki,Tonami, Hiroyuki,Nagahata, Ritsuko,Tawaki, Shin-ichiro,Uyama, Hiroshi,Kobayashi, Shiro
, p. 375 - 379 (2007/10/03)
For structural control and analysis of an enzymatically synthesized polyphenol, peroxidase-catalyzed polymerization of p-t-butylphenol in a mixture of polar organic solvent and phosphate buffer has been examined in detail. The resulting products were subjected to preparative HPLC. Two dimers and one trimer were isolated and their structures were determined by 1H and 13C NMR. ESI-TOF mass analysis showed the formation of two kinds of dimer and of at least four kinds of trimer. These data clearly showed that the polymer was composed of a mixture of phenylene and oxyphenylene units. The ratio of phenylene and oxyphenylene units in the product could be controlled by changing the solvent composition. The phenylene unit linearly increased as a function of the water content in the mixed solvent.
