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摘要：苯并吡喃具有两种异构体，具有优良生物和药理活性。B-H反应是一种尤其在有机合成方面非常优良的合成方式，但是这种反应也具有比较明显的不足，比如反应时间过长等问题。48682
本论文首先选择邻羟基苯甲醛和丙烯腈在催化剂DABCO的条件下反应作为模型反应来合成苯并吡喃类似物，选择不相同的取代基（五种）、催化剂、反应物比例、反应温度和反应时间来观察其与反应最终收率的关系，以此来选取最优的反应条件。通过对反应的条件的筛选，我们发现催化剂为DABCO时，以邻羟基苯甲醛和丙烯腈为原料且与催化剂DABCO的比例为1:1:0.6，取代基为甲氧基，浴温100℃，反应24小时时得到的产物苯并吡喃类似物的收率最高。经过氢谱、红外光谱分析，推测得到了该化合物的结构。作为合成ROCK抑制剂最终产物的初始步骤，实验条件的改进大大提高了合成最终产物的效率。
毕业论文关键词： 苯并吡喃；贝里斯-希尔曼反应；催化剂；最优条件
Application of B-H Reaction in the Synthesis of Benzopyran Analogs
Abstract:Benzopyran has two isomers, with excellent biological and pharmacological activity. B-H reaction is a very good way of synthesis, especially in organic synthesis, but this reaction also has obvious shortcomings, such as the reaction time is too long and so on.
The first choice of ortho hydroxy benzaldehyde and acrylonitrile in catalyst of DABCO under the condition of reaction was used as a model reaction to synthesis of benzopyran analogs, choose different substituted groups (five), catalyst, reactant ratio, reaction temperature and reaction time to observe the and the final yield of the relationship, in order to select the optimum conditions of the reaction. Through screening of reaction conditions, we found that the catalyst DABCO, ortho hydroxy benzaldehyde and acrylonitrile as raw material and catalyst DABCO and proportion for 1:1:0.6 and substituent for methoxy, bath temperature of 100 DEG C, reaction 24 hours to get the product of benzopyran analogs received the highest rate of. The structure of the compound was obtained by the analysis of the hydrogen spectrum and infrared spectrum. As an initial step in the synthesis of the final product of the ROCK inhibitor, the improvement of the experimental conditions greatly improves the efficiency of the final product.
Keyword: Chromene； Baylis-Hillman reaction； Catalyst； Optimal conditions；
目录
1 绪论 3
1.1 苯并吡喃简介 3
1.2 苯并吡喃的应用 3
1.2.1 抗病毒和抗氧化活性 3
1.2.2 提高免疫能力和降糖活性 4
1.2.3 在天然产物全合成方面的应用 4
1.3 贝里斯-希尔曼反应简介 5
1.3.1 贝里斯-希尔曼反应的应用 6
2 合成苯并吡喃类似物的方法研究 7
2.1 贝里斯-希尔曼反应在苯并吡喃类似物合成的研究 7
2.1.1 反应方法的发展 7
2.1.2 反应条件的发展 8
2.2 knoevenagel反应在苯并吡喃类似物合成的研究 13
2.3 微波辐射法在苯并吡喃类似物合成的研究 13
2.4 一锅法在苯并吡喃类似物合成的研究 14
3 B-H反应合成苯并吡喃类似物的实验部分