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Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids.
Chemical Communications ( IF 4.9 ) Pub Date : 2020-06-01 , DOI: 10.1039/d0cc02163f
Rui Lu 1 , Huifang Jiang , Xiaoqin Si , Xiaolin Luo , Fang Lu , Jie Xu
Affiliation  

Herein, we report a sustainable route for the synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived muconic acid and fumaric acid. The key Diels–Alder reaction constructed a cyclohexene framework substituted by four ester groups. The isolated yield of tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate was up to 95.5% without any catalyst used. And the hydrogenation reaction of the cycloadduct was catalyzed by commercial RANEY® Ni at room temperature and nearly 100% yield of the cyclohexyl target products was obtained.

中文翻译:

从糖衍生的羧酸可持续合成1,2,3,4-环己烷四羧酸酯。

本文中,我们报道了一种由糖衍生的粘康酸和富马酸合成1,2,3,4-环己烷四羧酸酯的可持续路线。关键的Diels-Alder反应构建了被四个酯基取代的环己烯骨架。在不使用任何催化剂的情况下,5-环己烯-1,2,3,4-四羧酸四甲酯的分离产率高达95.5%。然后在室温下通过商业RANEY®Ni催化环加合物的氢化反应,并获得接近100%的环己基目标产物收率。
更新日期:2020-07-07
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