Sciact
  • EN
  • RU

Catalytic synthesis of bioactive 2H-chromene alcohols from (-)-isopulegol and acetone on sulfonated clays Научная публикация

Журнал Reaction Kinetics, Mechanisms and Catalysis
ISSN: 1878-5190 , E-ISSN: 1878-5204
Вых. Данные Год: 2020, Том: 129, Номер: 2, Страницы: 627-644 Страниц : 18 DOI: 10.1007/s11144-020-01740-9
Ключевые слова Chromenol; Sulfonated clay; Isopulegol; Ketones
Авторы Laluc Mathias 1 , Maki-Arvela Paivi 1 , Peixoto Andreia F. 2 , Li-Zhulanov Nikolai 3,4 , Sandberg Thomas 1 , Salakhutdinov Nariman F. 3 , Volcho Konstantin 3,4 , Freire Cristina 2 , Sidorenko Alexander Yu 5 , Murzin Dmitry Yu 1
Организации
1 (Данные Web of science) Abo Akad Univ, Turku 20500, Finland
2 (Данные Web of science) Univ Porto, LAQV REQUIMTE, Fac Ciencias, Dept Quim E Bioquim, Rua Campo Alegre S-N, P-4169007 Porto, Portugal
3 (Данные Web of science) Novosibirsk Inst Organ Chem, Lavrentjev Av 9, Novosibirsk 630090, Russia
4 (Данные Web of science) Novosibirsk State Univ, Pirogova St 1, Novosibirsk 630090, Russia
5 (Данные Web of science) Natl Acad Sci Belarus, Inst Chem New Mat, Skaryna Str 36, Minsk 220141, BELARUS

Реферат: Condensation of (-)-isopulegol with acetone was investigated at 25-40 degrees C over clay based materials (K10, cloisite Na+ and halloysite nanotubes) modified with sulfonic acid groups by one-pot sulfonation with chlorosulfonic acid or via organosilylation with 2-(4-chlrosulfonylphenyl)-ethyltrimethoxysilane. The target product was the R diastereomer of dimethyl-substituted octahydro-2H-chromen-4-ol with exhibits antiviral activity. The catalysts were characterized by a range of physico-chemical methods. The effect of the initial isopulegol concentrations on the yield of ketone-derived chromenols and the R/S isomers ratio was studied for the first time. The best catalyst was a highly acidic, large pore K10-clay modified by sulfonic acid. Varying the initial concentration of the reagents allows to find a balance between dehydration by-products and a side etherification reaction. A high yield (73%) of the desired chromenols was reached using 0.52 mol/l initial (-)-isopulegol concentration after 240 min at 87% substrate conversion and reaction temperature 25 degrees C. The yield exceeded that of other previously reported in the open literature catalysts.
Библиографическая ссылка: Laluc M. , Maki-Arvela P. , Peixoto A.F. , Li-Zhulanov N. , Sandberg T. , Salakhutdinov N.F. , Volcho K. , Freire C. , Sidorenko A.Y. , Murzin D.Y.
Catalytic synthesis of bioactive 2H-chromene alcohols from (-)-isopulegol and acetone on sulfonated clays
Reaction Kinetics, Mechanisms and Catalysis. 2020. V.129. N2. P.627-644. DOI: 10.1007/s11144-020-01740-9 WOS Scopus РИНЦ OpenAlex
Файлы: Полный текст от издателя
Даты:
Опубликована online: 20 февр. 2020 г.
Опубликована в печати: 1 апр. 2020 г.
Идентификаторы БД:
Web of science: WOS:000516301700001
Scopus: 2-s2.0-85079669741
РИНЦ: 43248272
OpenAlex: W3007301671
Цитирование в БД:
БД Цитирований
Web of science 10
Scopus 12
РИНЦ 11
OpenAlex 13
Альметрики: