脂酶介导的酯溶剂和深共晶溶剂中苄基环戊酮的 Baeyer-Villiger 氧化反应。
Lipase-mediated Baeyer-Villiger oxidation of benzylcyclopentanones in ester solvents and deep eutectic solvents.
机构信息
Department of Food Chemistry and Biocatalysis, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland.
出版信息
Sci Rep. 2022 Aug 30;12(1):14795. doi: 10.1038/s41598-022-18913-2.
This work presents the chemo-enzymatic Baeyer-Villiger oxidation of α-benzylcyclopentanones in ester solvents as well as deep eutectic solvents (DES). In the first part of the work the effect of selected reaction conditions on the reaction rate was determined. The oxidation process was most effective in ethyl acetate at 55 °C, with the use of lipase B from Candida antarctica immobilized on acrylic resin and UHP as oxidant. Ultimately, these preliminary studies prompted the development of an effective method for the implementation of lipase-mediated Baeyer-Villiger oxidation of benzylcyclopentanones in DES. The highest conversion was indicated when the oxidizing agent was a component of DESs (minimal DESs). The fastest conversion of ketones to lactones was observed in a mixture of choline chloride with urea hydrogen peroxide. In this case, after 3 days, the conversion of the ketones to lactones products exceeded 92% for all substrates. As a result, two new lactones were obtained and fully characterized by spectroscopic data.
本工作展示了在酯溶剂和深共熔溶剂（DES）中α-苄基环戊酮的化学酶促 Baeyer-Villiger 氧化。在工作的第一部分，确定了所选反应条件对反应速率的影响。在 55°C 的乙酸乙酯中，使用固定在丙烯树脂上的南极假丝酵母脂肪酶 B 和 UHP 作为氧化剂，氧化过程最有效。最终，这些初步研究促使我们开发了一种有效的方法，用于在 DES 中实施脂肪酶介导的苄基环戊酮的 Baeyer-Villiger 氧化。当氧化剂是 DES 的组成部分（最小 DES）时，转化率最高。在氯化胆碱与尿素过氧化氢的混合物中，观察到酮向内酯的最快转化。在这种情况下，经过 3 天，所有底物的酮转化为内酯产物的转化率均超过 92%。结果，得到了两种新的内酯，并通过光谱数据进行了充分表征。
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