129488-49-9Relevant academic research and scientific papers
Metabolically stable tert-butyl replacement
Barnes-Seeman, David,Jain, Monish,Bell, Leslie,Ferreira, Suzie,Cohen, Scott,Chen, Xiao-Hui,Amin, Jakal,Snodgrass, Brad,Hatsis, Panos
supporting information, p. 514 - 516 (2013/07/26)
Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp3 C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.
Oxidation of Aromatic Compounds. V. Oxidation of Substituted Benzonitriles and 2,4,6-Triaryl-1,3,5-Triazines in System HSO3F-PbO2
Rudenko,Salfetnikova,Vasil'ev
, p. 1447 - 1470 (2007/10/03)
Low-temperature oxidation of substituted benzonitriles by the system HSO3F-PbO2 proceeds with intermediate formation of cation-radicals and leads to substitution of hydrogen atoms of the methyl group or benzene ring. This reaction provides a route for preparation of chloromethylsubstituted benzonitriles, diarylmethanes, diaryls, arylfluorosulfonates and substituted benzamides with cyano groups. In the case of methyl derivatives of 2,4,6-triphenyl-1,3,5-triazine substitution of the first and then the second hydrogen atom of the same methyl group transforms it into hydroxy or chloromethyl group, or into the aldehyde function.
