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目的轴手性联萘骨架是一类重要的手性结构类型,目前许多具有生理活性的天然产物被证实具有该核心骨架。除此之外,在有机反应中,多种具有轴手性联萘的化合物也被报道具有卓越的催化活性。鉴于该类结构的重要性,本文拟对轴手性1,1’-联萘骨架膦酸酯衍生物7的合成方法进行优化。方法该合成方法的优化以产率为指标,主要包括反应时间、投料顺序以及反应后处理等工艺的调整。结果优化后,减少了大量的反应时间;通过调整格氏试剂的制备方法,提高了反应的成功率;整条合成路线仅3步需经硅胶柱分离纯化;各个步骤均具有较高的收率。结论本文提出的轴手性1,1’-联萘骨架膦酸酯衍生物7合成方法简便高效,对该结构的后续研究具有重要的参考价值。
Purpose Axis Chiral binaphthyl skeletons are an important class of chiral structures and many of the currently physiologically active natural products have been shown to possess this core framework. In addition to this, a variety of compounds having a shaft chiral binaphthyl are reported to have excellent catalytic activity in organic reactions. In view of the importance of this kind of structure, this paper intends to optimize the synthesis method of 7-binaphthyl skeleton phosphonate derivative 7. Methods The optimization of the synthesis method takes the yield as an index, mainly including the adjustment of the reaction time, the sequence of feeding and the reaction post-treatment. After optimization, a large amount of reaction time was reduced; the success rate of the reaction was improved by adjusting the preparation method of Grignard reagent; the whole synthesis route was separated and purified by silica gel column only in three steps; all steps had higher yield . CONCLUSIONS The proposed method for the synthesis of 1 ’- binaphthyl skeleton phosphonate derivative 7 is simple and efficient, and has important reference value for the follow-up study of this structure.