基于ZSM-5的微孔-中孔催化剂上(-)-异蒲勒醇与苯甲醛Prins环化反应合成药物

doi:10.1016/S1872-2067(19)63305-X

催化学报 ›› 2019, Vol. 40 ›› Issue (11): 1713-1720.DOI: 10.1016/S1872-2067(19)63305-X

基于ZSM-5的微孔-中孔催化剂上(-)-异蒲勒醇与苯甲醛Prins环化反应合成药物

Ekaterina Kholkina^a, Paivi Maki-Arvela^a, Chloe Lozachmeuer^a, Roman Barakov^b, Nataliya Shcherban^b, Dmitry Yu. Murzin^a

a 博阿卡德米大学科学与工程系, 约翰·盖多林过程化学中心, 土尔库 20500, 芬兰;
b 乌克兰国家科学院L. V. Pisarzhevsky物理化学研究所, 基辅 03028, 乌克兰

收稿日期:2018-12-07 修回日期:2019-01-17 出版日期:2019-11-18 发布日期:2019-09-06
通讯作者: Dmitry Yu. Murzin

Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

Ekaterina Kholkina^a, Paivi Maki-Arvela^a, Chloe Lozachmeuer^a, Roman Barakov^b, Nataliya Shcherban^b, Dmitry Yu. Murzin^a

a Johan Gadolin Process Chemistry Centre, Faculty of Science and Engineering, Åbo Akademi University, Turku 20500, Finland;
b L.V. Pisarzhevsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 pr. Nauky, Kiev 03028, Ukraine

Received:2018-12-07 Revised:2019-01-17 Online:2019-11-18 Published:2019-09-06
Contact: Dmitry Yu. Murzin

摘要/Abstract

摘要： 将数个ZSM-5基微孔-中孔催化剂用于（-）-异蒲勒醇与用作反应物和溶剂的苯甲醛进行Prins环化反应，合成杂环含氧2H-色烯衍生物，其包含四氢吡喃结构并表现出生物活性.采用N₂吸附，氨-程序升温还原，吡啶和2，6-二-叔丁基吡啶吸附-脱附的红外光谱表征了所考察的催化剂.当在含适量强酸位和12倍所需产物尺寸的中孔的催化剂上，于70 oC下进行Prins反应，（-）-异蒲勒醇完全转化时所需产物产率最高达67%.

关键词: 微孔-中孔材料, Prins成环反应, 四氢吡喃

Abstract: Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chromene derivatives including the tetrahydropyran structure and exhibiting biological activity. The investigated catalysts were characterized by nitrogen adsorption, ammonia temperature programmed desorption, adsorption-desorption of pyridine and 2,6-di-tert-butylpyridine with Fourier transform infrared spectroscopic control. For the Prins reaction performed at 70℃, the highest yield of the desired product, equal to 67% at complete conversion of (-)-isopulegol, was obtained over a micro-mesoporous catalyst containing an optimum amount of strong acid sites and mesopores, being 12 fold larger than the size of the desired product.

Key words: Micro-mesoporous material, Prins cyclisation, Tetrahydropyran

Ekaterina Kholkina, Paivi Maki-Arvela, Chloe Lozachmeuer, Roman Barakov, Nataliya Shcherban, Dmitry Yu. Murzin. 基于ZSM-5的微孔-中孔催化剂上(-)-异蒲勒醇与苯甲醛Prins环化反应合成药物[J]. 催化学报, 2019, 40(11): 1713-1720.

Ekaterina Kholkina, Paivi Maki-Arvela, Chloe Lozachmeuer, Roman Barakov, Nataliya Shcherban, Dmitry Yu. Murzin. Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals[J]. Chinese Journal of Catalysis, 2019, 40(11): 1713-1720.

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基于ZSM-5的微孔-中孔催化剂上(-)-异蒲勒醇与苯甲醛Prins环化反应合成药物

Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

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