Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity

Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity Научная публикация

Журнал

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Вых. Данные

Год: 2014, Том: 397, Страницы: 48-55 Страниц : 8 DOI: 10.1016/j.molcata.2014.10.023

Авторы

Torozova Alexandra ¹ , Mäki-Arvela Päivi ¹ , Aho Atte ¹ , Kumar Narendra ¹ , Smeds Annika ¹ , Peurla Markus ² , Sjöholm Rainer ¹ , Heinmaa Ivo ³ , Korchagina Dina V. ⁴ , Volcho Konstantin P. ^4,5 , Salakhutdinov Nariman F. ^4,5 , Murzin Dmitry Yu. ¹

Организации

1	Process Chemistry Centre, Åbo Akademi University, 20500 Turku/Åbo, Finland
2	University of Turku,Turku, Finland
3	Institute of Chemical Physics and Biophysics, Tallinn, Estonia
4	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Russian Academy of Sciences, Novosibirsk 630090, Russia
5	Novosibirsk State University, Novosibirsk 630090, Russia

Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Fe-modified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 °C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.

Torozova A. , Mäki-Arvela P. , Aho A. , Kumar N. , Smeds A. , Peurla M. , Sjöholm R. , Heinmaa I. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F. , Murzin D.Y.
Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity
Journal of Molecular Catalysis A: Chemical. 2014. V.397. P.48-55. DOI: 10.1016/j.molcata.2014.10.023 WOS Scopus РИНЦ OpenAlex

Web of science:	WOS:000349575000005
Scopus:	2-s2.0-84911495619
РИНЦ:	23956948
OpenAlex:	W1994228644

БД	Цитирований
OpenAlex	18
Scopus	19