N.N. Vorozhtsov Institute of Organic Chemistry SB RAS, Academician Lavrentiev Ave. 9, 630090 Novosibirsk, Russia.
Voevodsky Institute of Chemical Kinetics and Combustion SB RAS, Institutskaya 3, 630090 Novosibirsk, Russia.
Molecules. 2022 Mar 16;27(6):1922. doi: 10.3390/molecules27061922.
Pyrrolidine nitroxides with four bulky alkyl substituents adjacent to N-O group are known for their high resistance to bioreduction. The 3,4-unsubstituted 2--butyl-2-ethylpyrrolidine-1-oxyls were prepared from the corresponding 2--butyl-1-pyrroline-1-oxides via either the addition of ethinylmagnesium bromide with subsequent hydrogenation or via treatment with ethyllithium. The new nitroxides showed excellent stability to reduction with ascorbate with no evidence for additional large hyperfine couplings in the EPR spectra.
具有四个相邻于 N-O 基团的大体积烷基取代基的吡咯烷氮氧自由基以其对生物还原的高抗性而闻名。通过添加乙炔基溴化镁随后氢化,或者通过用乙基锂处理,可从相应的 2-丁基-1-吡咯啉-1-氧化物制备 3,4-未取代的 2-丁基-2-乙基吡咯烷-1-氧自由基。新的氮氧自由基对抗坏血酸还原具有极好的稳定性,在 EPR 光谱中没有额外的大超精细耦合的证据。