CN112110887A - 一种3位甲酰基取代的2h-色烯衍生物的合成方法及其应用 - Google Patents
一种3位甲酰基取代的2h-色烯衍生物的合成方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种新的在色烯结构中引入醛基的方法，其结构如式Ⅰ所示。通过以相应水杨醛为原料，与丙二腈缩合后，在碱性条件下双键断裂生成醛，该法产量高，反应条件温和，产品纯度高且易于分离。醛基的引入可减弱ACQ效应，增强染料在质子溶剂中的荧光量子产率，可使染料分子的荧光光谱红移，增强了染料分子的荧光性能，还消除了部分荧光探针在生物细胞中易于淬灭的局限性，在荧光探针、生命分析等领域有着广阔的应用前景。
Description
【技术领域】
本发明属于有机化学合成以及荧光染料开发领域，具体涉及一种3位甲酰基取代的2H-色烯衍生物的合成方法及其应用。
【背景技术】
2H-色烯是许多药物和具有生理活性天然产物的重要结构单元，含有这类骨架的化合物在消炎、抗真菌的研究中表现出良好的活性。因此，发展官能化的2H-色烯具有十分重要的意义。然而，目前的方法在3位引入取代基十分具有挑战性，常用丙烯醛与水杨醛进行缩合在色烯母核上引入醛基。然而，丙烯醛是无色透明有恶臭的液体，蒸汽有极强刺激性与催泪性，且极度易燃。目前使用目前已发展的合成方法限制了2H-色烯天然产物的全合成及药物化学的研究。因此，发展新的方法解决相关的合成问题具有重要的研究意义。
【发明内容】
本发明的第一个目的在于克服现有技术的不足，提供一种3位甲酰基取代的2H-色烯衍生物的合成方法，所述2H-色烯衍生物具有式I所示的结构：
其中，R选自C1～C4烷基。
所述方法包括下述步骤：
1)
以取代水杨醛A为原料，碱存在下与3-溴丙炔反应得B；
2)
将B与丙二腈在碘化亚铜催化下反应得C；
3)
中间体C在碱性条件下可反应得到目标产物Ⅰ；
步骤(1)中，所述碱选自叔丁醇钾或碳酸钾，反应溶剂选自乙腈或N,N-二甲基甲酰胺，反应溶剂选自乙腈或N,N-二甲基甲酰胺，取代水杨醛与3-溴丙炔摩尔比为1:1～2，反应温度20～40℃；；
步骤(2)中，溶剂为乙腈，中间体1与丙二腈摩尔比为1:1～1.5，反应时间为1～2h，反
应温度为70～90℃；
步骤(3)中，C溶液的溶剂为甲醇或乙醇，氢氧化钠溶液的pH值需大于11，氢氧化钠与化合物C的用量比为1.2～1.8，回流温度为60～90℃，反应时间2～4h。
本发明的第二个目的是提供一种3位甲酰基取代的2H-色烯衍生物在荧光染料的应用。通过荧光光谱发现3位甲酰基取代的2H-色烯衍生物具有强的荧光发射能力，在荧光染料方面有应用价值。
本发明与现有技术相比具有如下优点：
1、提供的合成方法反应条件温和、合成操作简单，产物易于分离提纯、不使用丙烯醛。
2、本发明制备的3位甲酰基取代的2H-色烯衍生物具有强的荧光发射能力，在荧光染料方面具有应用价值。
【附图说明】
图1是实施例1制备的化合物B1的核磁氢谱。
图2是实施例1制备的化合物C1的核磁氢谱。
图3是实施例1制备的化合物I1的核磁氢谱。
图4是I1的紫外-可见光吸收光谱图。
图5是I1的荧光发射光谱图。
【具体实施方式】
下面通过具体实施例对本发明进行说明，但本发明并不局限于此。
下述实施例所述的实验方法，如无特殊说明，均属常规方法；所述药品和溶剂，均可从商业途径购买。
【实施例1】
制备中间体B1：
1.546g(0.008mol)4-二乙氨基水杨醛A1和2.211g(0.016mol)K2CO3于50mL烧瓶中，再加入30mL乙腈，再向其中加入1.428(0.012mol)3-溴丙炔，常温搅拌6h，溶液变为浅棕色，TLC检测反应至反应完全。加水与二氯甲烷萃取后真空干燥烘干，得到1.68g棕色晶体B1，产率96.78％。1H NMR(500MHz,Chloroform-d)δ8.24(d,J＝9.3Hz,1H),8.01(s,1H),6.37(dd,J＝9.3,2.4Hz,1H),6.18(d,J＝2.4Hz,1H),4.77(d,J＝2.4Hz,2H),3.46(q,J＝7.1Hz,4H),2.59(t,J＝2.4Hz,1H),1.25(t,J＝7.1Hz,6H).
【实施例2】
制备中间体C1：
称取1.52g(0.007mol)中间体B1化合物于50mL干燥的烧瓶，加入0.67g(0.0035mol)碘化亚铜，再加入25mL乙腈升温至80℃后加入0.555g丙二腈，搅拌2h后溶液呈深红色，TLC检测反应至反应完全，冷却后抽滤，用二氯甲烷洗涤，真空干燥烘干，得紫黑色固体1.48g，产率75.66％。1H NMR(500MHz,DMSO-d6)δ＝7.69(s,1H),7.43(s,1H),7.16(d,J＝8.8Hz,1H),6.44(dd,J＝8.9,2.4Hz,1H),6.17(d,J＝2.3Hz,1H),5.26(s,2H),3.45(q,J＝7.0Hz,4H),1.13(t,J＝7.0Hz,6H).
【实施例3】
制备式I1化合物：
称取0.56g(0.002mol)中间体2化合物于25mL烧瓶，将0.8g(0.02mol)氢氧化钠溶于7.5mL乙醇与7.5mL水均匀混合的溶液中，将混合液加入烧瓶，搅拌回流2h，溶液变为橙红色，TLC检测反应至完全。用二氯甲烷萃取后真空干燥，柱层析分离得棕红色固体0.40g，产率86.5％。1H NMR(500MHz,DMSO-d6)δ9.39(s,1H),7.47(s,1H),7.16(d,J＝8.6Hz,1H),6.36(dd,J＝8.8,2.4Hz,1H),6.12(d,J＝2.4Hz,1H),4.85(s,2H),3.37(q,J＝7.0Hz,4H),1.10(t,J＝6.9Hz,6H).
【实施例4】
配制10μmol/L的I1的水溶液，测试其紫外-可见吸收光谱、荧光发射光谱图。
上述实施例中目标分子I1在水溶液中的光物理性质见表1：
表1：I1的光物理性质
Claims (4)
1.一种3位甲酰基取代的2H-色烯衍生物，其特征在于，结构式下：
式Ⅰ中，R为碳原子数小于等于4的烷基。
2.一种如权利要求1所述的化合物的合成方法，其特征在于，合成路线如下：
具体步骤：(1)以4位取代水杨醛A为原料，碱存在下与3-溴丙炔反应得B；
2)将B与丙二腈在碘化亚铜催化下反应得C；
3)化合物C的溶液加入氢氧化钠水溶液，加热得到目标产物Ⅰ。
3.如权利要求2所述的合成步骤(3)，其特征在于：C溶液的溶剂为甲醇或乙醇，氢氧化钠溶液的pH值需大于11，氢氧化钠与化合物C的用量比为1.2～1.8，回流温度为60～90℃，反应时间2～4h。
4.权利要求1所述化合物的应用，具体为：有机发光材料、有机荧光染料、荧光探针及细胞成像类的荧光染料的应用。
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