Unexpected synthesis and crystal structure of N-{2-[2-(2-acetylethenyl)phenoxy]ethyl}-N-ethenyl-4-methylbenzenesulfonamide

The title compound, C21H23NO4S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O⋯H - C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-dehydrogenase (85% probability), as well as to act as a mucomembranous protector (73%). © 2020.

Авторы
Издательство
International Union of Crystallography
Язык
Английский
Страницы
1851-1853
Статус
Опубликовано
Том
76
Год
2020
Организации
  • 1 Department of Chemistry, College of Natural and Computational Sciences, University of Gondar, Gondar, 196, Ethiopia
  • 2 Faculty of Chemistry, Vnu University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Hanoi, 100000, Viet Nam
  • 3 Faculty of Science, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya, Moscow, 117198, Russian Federation
  • 4 Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc, Viet, Hanoi, Viet Nam
  • 5 N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Kosygina 4, Moscow, Russian Federation
  • 6 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, 119991, Russian Federation
Ключевые слова
crystal structure; enamine; PASS software; Petrenko-Kristchenko reaction
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