化学
亲脂性
哌啶
构象异构
立体化学
分子
群(周期表)
组合化学
有机化学
作者
Ivan G. Logvinenko,Ivan S. Kondratov,Stanislav O. Pridma,Nataliya A. Tolmachova,Roman N. Morev,Violetta G. Dolovanyuk,Andrii Boretskyi,Roman O. Stepaniuk,Serhii Trofymchuk,Christian Mück‐Lichtenfeld,Constantin G. Daniliuc,Günter Haufe
标识
DOI:10.1016/j.jfluchem.2022.109990
摘要
Conformational and electronic effects of the trifluoromethoxy group make it attractive to be introduced in biorelevant structures. A mini-library of CF3O-substituted piperidines, pyrrolidines and azetidines was synthesized in 4-5 steps from commercial amino alcohols. Comparison of the measured pKa- and log D7.4 values of selected regioisomeric CF3O piperidines with the corresponding CF3- and MeO analogues shows that the effect on the acid/base properties and lipophilicity is rather complex and depends of the substitution position and the conformation of the molecules. For the most stable conformers of β-OCF3 compounds 2-(trifluoromethoxymethyl)piperidine (1c) and 3-trifloromethoxypiperidine (1e), DFT calculations and X-ray data (for 1c) show a favored gauche-arrangement with regard to the amino group.
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