二苯乙烯类化合物的双键有顺、反两种构型,分别在医药、食品保健、化学、光学、电子、材料科学等领域具有很大的应用潜力。本文基于国内外学者对二苯乙烯类化合物合成方法的研究,总结了二苯乙烯类化合物双键顺、反构型的异构化反应,希望为相关研究工作者提供参考。
Two types of stilbenes with cis-trans double bond have great application potential in medicine, food health, chemistry, optics, electronics, and material science and so on. Based on the studies on the synthesis of stilbene compounds at home and abroad, this paper reviews the progress on the cis-trans-isomerization reactions of double bond in the stilbene compounds.
Matthew J等人以顺式二苯乙烯类化合物为原料,双–(乙腈)氯化钯(II)为催化剂,通过双键异构化合成构型单一的反式二苯乙烯(图1) [21] 。该体系以二氯甲烷为溶剂,在室温条件搅拌14小时,将反应混合物用乙醚稀释并通过Florisil过滤,用乙醚洗脱。减压除去溶剂,通过快速硅胶色谱法(二乙醚–己烷2:98,Rf = 0.52)纯化残余物,得到100%反式构型的二苯乙烯。
图1. 钯催化的双键异构化
2.1.2. 二苯二硫醚催化的顺反异构化
Francisco Alonso等人报道了以顺式和反式两种构型的二苯乙烯类混合物为原料,二苯二硫醚为催化剂的双键异构化反应(图2) [22] 。将原料溶于四氢呋喃溶液中,加入催化剂和引发剂偶氮二异丁腈(AIBN),搅拌回流8小时。将反应后的混合物体系用乙酸乙酯萃取有机相,经过水洗、饱和食盐水洗、无水硫酸镁干燥、过滤,再减压除去溶剂,通过快速硅胶色谱法纯化产物,得到100%反式构型的二苯乙烯类化合物。
邵智博,杜文超. 二苯乙烯类化合物的顺反异构化反应研究进展Progress on Cis-Trans Isomerization Reactions of Stilbenes[J]. 有机化学研究, 2019, 07(01): 11-17. https://doi.org/10.12677/JOCR.2019.71002
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