2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties

2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties Научная публикация

Журнал

Molecules
, E-ISSN: 1420-3049

Вых. Данные

Год: 2020, Том: 25, Номер: 4, Номер статьи : 845, Страниц : DOI: 10.3390/molecules25040845

Ключевые слова

nitroxides; nitrones; 1,3-dipolar cycloaddition reaction; organolithium compounds; EPR; spin probes; reduction kinetics

Авторы

Zhurko Irina E. ¹ , Dobrynin Sergey ¹ , Gorodetskii Artem A. ¹ , Glazachev Yuri, I ² , Rybalova Tatyana, V ¹ , Chernyak Elena, I ¹ , Asanbaeva Nargiz ^1,3 , Bagryanskaya Elena G. ¹ , Kirilyuk Igor A. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Inst Chem Kinet & Combust SB RAS, Inst Skaya 3, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova St, Novosibirsk 2, Russia

Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.

Zhurko I.E. , Dobrynin S. , Gorodetskii A.A. , Glazachev Y.I. , Rybalova T.V. , Chernyak E.I. , Asanbaeva N. , Bagryanskaya E.G. , Kirilyuk I.A.
2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties

Molecules. 2020. V.25. N4. 845 . DOI: 10.3390/molecules25040845 WOS Scopus РИНЦ

Полный текст от издателя

Опубликована online:

14 февр. 2020 г.

Web of science	WOS:000522454500081
Scopus	2-s2.0-85079610677
РИНЦ	43241936
OpenAlex	W3006016581