丹皮酚单硝化与二硝化衍生物的合成

Synthesis of the mononitrated and dinitrated derivatives of paeonol

文章以浓硝酸/浓硫酸作为硝化剂,对丹皮酚的硝化反应进行研究。在丹皮酚与硝酸的摩尔比为1∶1、1∶3的情况下,分别合成了丹皮酚的单硝基取代、二硝基取代产物,其中单硝基取代产物经过硅胶柱层析分离得到5-硝基丹皮酚、3-硝基丹皮酚单一产物。所得产物经FTIR、1H-NMR、MS测试确认结构,收率分别为58.1%、29.3%和90.0%。文章在成功合成了3种硝化产物的基础上,对硝基引入产生的理化性质变化进行了阐述。

The nitration of paeonol（2 hydroxyl-4-methoxyacetophenone）is studied by using concentrated nitric acid as the nitrating agent in the presence of concentrated sulfuric acid. Under the condition of reacting with equal quantity of HNO3, only mono nitrated derivatives formed. After separating and purifying silica gel column, 5-nitro and 3 nitro derivative of paeonol were obtained with the yield of 58. 1% and 29.3% respectively. When changing the mole ratio to 1 ： 3, the single 3,5 dinitro substituted product was obtained with the yield of 90.0%. The three kinds of structures were characterized by means of IR,^1H NMR, and MS. The change of physicochemical properties caused by the nitro group was discussed on the basis of the synthesis of the three kinds of nitrated products.