CN114773259A - 一种吡啶功能化水溶性柱[5]芳烃及其制备方法 - Google Patents
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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Abstract
本发明公开了一种属于有机合成领域，涉及一种吡啶功能化水溶性柱[5]芳烃及其制备方法。所述吡啶功能化水溶性柱[5]芳烃的制备方法包括以下步骤：(1)使用1,1‑二溴代对苯二烷基醚及多聚甲醛制备柱[5]芳烃S‑I或S‑II；(2)使用柱[5]芳烃与吡啶反应制备吡啶功能化水溶性柱[5]芳烃I或II。本发明所涉及的吡啶功能化水溶性柱[5]芳烃的制备方法具有原料成本低、收率高、可操作性强及后处理方便等优点。本发明所涉及的吡啶功能化水溶性柱[5]芳烃在水溶液中具有良好的溶解性，并对线性烷基二酸存在一定的络合作用。
Description
技术领域
本发明公开了属于有机合成技术领域的一种吡啶功能化水溶性柱[5]芳烃及其制备方法。
背景技术
大多数生物过程都发生在水介质中，水溶液中的非共价相互作用对于更好地理解和调控自然界中的很多过程至关重要。由于大多数的有机化合物在水中的溶解性都比较差，如何构筑具有高亲和力和高选择性的水溶性受体，用于与水中的客体分子结合，一直是主-客体化学发展的挑战性课题。
水溶性柱[5]芳烃作为一类新型的超分子大环主体化合物，由于其在水溶液中良好的溶解性及独特的主-客体结合特性而受到广泛关注。水溶性柱[5]芳烃可广泛应用于络合水中的阴、阳离子和在水中溶解性差的中性有机小分子，从而在离子检测及传感，水中有机污染物的处理及分离，药物递送及控释，光捕获，抑制细菌生物膜的形成等方面发挥重要作用，但目前已发展的水溶性柱[5]芳烃的种类较少，制备方法也较为复杂。鉴于水溶性柱[5]芳烃在主-客体化学领域的重要作用，通过一条成本低、反应条件温和、简单高效且易于分离的路线制备一类吡啶功能化的水溶性柱[5]芳烃具有重要的应用价值。
发明内容
本发明的目的是为了克服现有的水溶性柱[5]芳烃种类较少且制备方法较为复杂等问题，提供一类吡啶功能化水溶性柱[5]芳烃。
为了实现上述目的，本发明提供了一种高效便捷且条件温和的合成一类吡啶功能化水溶性柱[5]芳烃的方法，并研究了其在水溶液中对线性烷基二酸的络合作用。所述吡啶功能化水溶性柱[5]芳烃具有式I所示的结构：
其制备方法如式II所示：
下面对本发明进行分步骤说明，即对上式中的各步骤按照顺序进行一步一步地具体说明。
第一步骤是柱[5]芳烃S-I或S-II的制备：
将1,1-二溴代对苯二烷基醚A或B以及磁子加入三口烧瓶中，在氮气环境下加入1,2-二氯乙烷，剧烈搅拌30min后，将三颈烧瓶移至低温反应浴槽中，于0℃下加入三氟化硼·乙醚溶液，10min后将三颈烧瓶移至25℃，反应2h；经TLC(展开剂为V石油醚:V二氯甲烷＝1:1)监测体系，确认原料A或B反应完全后，倒入含有甲醇的烧杯中，用布氏漏斗抽滤后得到固体，柱层析(展开剂V石油醚:V二氯甲烷＝2:1)，得到相应的柱[5]芳烃S-I或S-II。本步骤的反应式如下：
第二步骤是吡啶功能化水溶性柱[5]芳烃I或II的制备：
向圆底烧瓶中加入柱[5]芳烃S-I或S-II与磁子，在氮气环境下加入无水吡啶，120℃下回流反应72h；待柱[5]芳烃S-I或S-II完全转化后将体系移出油浴锅，冷却至室温后有固体析出，用砂芯漏斗抽滤，得到的固体用少量二氯甲烷洗涤，最终得到吡啶功能化水溶性柱[5]芳烃I或II。本步骤的反应式如下：
所述第一步骤中1,1-二溴代对苯二烷基醚、多聚甲醛及三氟化硼乙醚的摩尔比为1.0:(2.0-3.0):1.0。
所述第一步骤中甲醇的用量为：每1.0g 1,1-二溴代对苯二烷基醚A或B，加入20-36mL甲醇。
所述第二步骤中吡啶的用量为：每100.0mg柱[5]芳烃S-I或S-II，加入1.0-3.0mL吡啶。
相较于传统方法，本发明的有益效果为：
(1)本发明设计合成了一类新型的吡啶功能化柱[5]芳烃，其制备方法具有原料成本低、收率高、可操作性强及后处理方便等优点；
(2)本发明所涉及的吡啶功能化水溶性柱[5]芳烃在水溶液中具有良好的溶解性，并对线性烷基二酸存在一定的络合作用。
附图说明
图1为实施例1制备的化合物(I)的NMR图谱；
图2为实施例2制备的化合物(II)的NMR图谱；
图3为吡啶功能化水溶性柱芳烃I(5.0mM)与四种线性烷基二酸(25.0mM)在重水中作用的局部1H NMR图谱；所截取的化学位移范围为7.5-9.2ppm；其中：a)吡啶功能化水溶性柱[5]芳烃I；b)吡啶功能化水溶性柱[5]芳烃I+己二酸；c)吡啶功能化水溶性柱[5]芳烃I+庚二酸；d)吡啶功能化水溶性柱[5]芳烃I+辛二酸；e)吡啶功能化水溶性柱[5]芳烃I+壬二酸；
图4为吡啶功能化水溶性柱芳烃I(5.0mM)与四种线性烷基二酸(25.0mM)在重水中作用的局部1H NMR图谱；所截取的化学位移范围为3.1-7.0ppm；其中：a)吡啶功能化水溶性柱[5]芳烃I；b)吡啶功能化水溶性柱[5]芳烃I+己二酸；c)吡啶功能化水溶性柱[5]芳烃I+庚二酸；d)吡啶功能化水溶性柱[5]芳烃I+辛二酸；e)吡啶功能化水溶性柱[5]芳烃I+壬二酸。
图5为吡啶功能化水溶性柱芳烃I(5.0mM)与四种线性烷基二酸(25.0mM)在重水中作用的局部1H NMR图谱；所截取的化学位移范围为-7.0-4.0ppm；其中：a)吡啶功能化水溶性柱[5]芳烃I+己二酸；b)吡啶功能化水溶性柱[5]芳烃I+庚二酸；c)吡啶功能化水溶性柱[5]芳烃I+辛二酸；d)吡啶功能化水溶性柱[5]芳烃I+壬二酸。
具体实施方式
在本文中通过具体实施例对本发明的方法进行说明，但本发明并不局限于此，在本发明的技术构思范围内，进行任何的修改、等同替换和改进等，均应包括在本发明的保护范围之内。
实施例1：
本发明提供了一种制备吡啶功能化水溶性柱[5]芳烃I的方法，按照以下步骤进行:
第一步骤是柱[5]芳烃S-I的制备：称取5.01g单体A和0.93g(2.0当量)多聚甲醛固体置于250mL三颈烧瓶中，放入磁子，在氮气环境下加入115mL1,2-二氯乙烷溶液，剧烈搅拌30min后，将三颈烧瓶移至低温反应浴槽中，于0℃下加入3.9mL(1.0当量)三氟化硼·乙醚溶液，10min后将三颈烧瓶移至25℃，反应2h。经TLC(展开剂为V石油醚:V二氯甲烷＝1:1)监测体系，确认原料单体A反应完全后，倒入含有100mL甲醇溶液的烧杯中，用布氏漏斗抽滤后得到固体，柱层析(展开剂V石油醚:V二氯甲烷＝2:1)，得到柱[5]芳烃衍生物S-I，产率为91％。该化合物是已知化合物，1H NMR、13C NMR与标准谱图一致。
第二步骤是吡啶功能化水溶性柱[5]芳烃I的制备：称取100mg柱[5]芳烃S-I于25mL圆底烧瓶中，加入磁子，在氮气环境下加入3.0mL无水吡啶，120℃下回流反应72h。待原料柱[5]芳烃S-I完全转化后将体系移出油浴锅，待体系冷却至室温后有固体析出，用砂芯漏斗抽滤，得到的固体用少量二氯甲烷洗涤，最终得到吡啶功能化水溶性柱[5]芳烃I，产率为92％。
I的核磁数据如下：
1H NMR(500MHz,D2O)δ8.68(d,J＝6.0Hz,20H),8.28(t,J＝7.5Hz,10H),7.86(t,J＝7.5Hz,20H),6.50(s,10H),4.90(t,J＝5.0Hz,20H),4.44(t,J＝4.5Hz,20H),3.38(s,10H)ppm.
13C NMR(125MHz,CO3OD)δ150.6,147.4,146.4,130.1,129.4,116.7,68.8,62.3,30.3ppm.
实施例2
本发明还提供了一种制备吡啶功能化水溶性柱[5]芳烃II的方法，按照以下步骤进行:
第一步骤是柱[5]芳烃S-II的制备：称取4.2g单体B和1.07g(3.0当量)多聚甲醛固体置于250mL三颈烧瓶中，放入磁子，在氮气环境下加入90mL 1,2-二氯乙烷溶液，然后剧烈搅拌30min后，将三颈烧瓶移至低温反应浴槽中，于0℃下加入3.0mL(1.0当量)三氟化硼·乙醚溶液，10min后将三颈烧瓶移至室温，反应2h。经TLC(展开剂为V石油醚:V二氯甲烷＝1:1)监测体系，确认原料单体B反应完全后，倒入含有150mL甲醇溶液的烧杯中，用布氏漏斗抽滤后得到固体，柱层析(展开剂V石油醚:V二氯甲烷＝2:1)，得到柱[5]芳烃S-II，产率为78％。该化合物是已知化合物，1H NMR、13C NMR与标准谱图一致。
第二步骤是吡啶功能化水溶性柱[5]芳烃II的制备：称取300mg柱[5]芳烃S-II于25mL圆底烧瓶中，加入磁子，在氮气环境下加入3.0mL无水吡啶，120℃下回流反应72h。待原料柱[5]芳烃S-II完全转化后将体系移出油浴锅，待体系冷却至室温后有固体析出，用砂芯漏斗抽滤，得到的固体用少量二氯甲烷洗涤，最终得到吡啶功能化水溶性柱[5]芳烃II，产率为89％。
II的核磁数据如下：
1H NMR(500MHz,D2O)δ8.68(d,J＝5.5Hz,20H),8.38(t,J＝7.0Hz,12H),7.92(t,J＝7.0Hz,10H),6.65(s,10H),4.76(t,J＝7.0Hz,20H),3.94(t,J＝5.0Hz,20H),3.56(s,10H),2.45(t,J＝5.5Hz,20H)ppm.
13C NMR(125MHz,CD3OD)δ150.9,147.0,146.1,130.2,129.6,116.8,67.2,60.6,32.3,30.6ppm.
发明人对按照上述方法制备的吡啶功能化水溶性柱[5]芳烃I进行了试验。
通过图3、图4对比可以看出，当将线性烷基二酸加入吡啶功能化水溶性柱[5]芳烃I的重水溶液中后，该主体分子上的H(包括柱[5]芳烃骨架和吡啶盐)均发生了相应位移。即己二酸、庚二酸、辛二酸和壬二酸均和主体分子I发生了络合。由此表明了吡啶功能化水溶性柱[5]芳烃I可以络合水中的线性烷基二酸。
通过图5可以看出，将线性烷基二酸加入吡啶功能化水溶性柱[5]芳烃I的重水溶液中后，在高场区域(<0ppm)均观察到了核磁信号峰，说明这些线性二酸的亚甲基H受到了柱[5]芳烃柱状大环的强屏蔽效应。即己二酸、庚二酸、辛二酸和壬二酸均和主体分子I发生了络合作用，这些烷基线性二酸通过疏水相互作用穿入了柱[5]芳烃的空腔。上述试验进一步表明了吡啶功能化水溶性柱[5]芳烃I可以络合水中的线性烷基二酸。
上述实施例中，g代表“克”；mg代表“毫克”，mL代表“毫升”；h代表“小时”；℃代表“摄氏度”；DCE代表1,2-二氯乙烷；TLC代表薄层色谱。
由上述实施例可以看出，按照本发明所述的合成吡啶功能化水溶性柱[5]芳烃的方法，可在温和条件下，高效便捷的获得目标产物。本发明所述的吡啶功能化水溶性柱[5]芳烃在水溶液中具有良好的溶解性，并对线性烷基二酸存在一定的络合作用。
Claims (4)
1.一种吡啶功能化水溶性柱[5]芳烃及其制备方法，所述吡啶功能化水溶性柱[5]芳烃具有式I所示的结构：
其制备方法按照式II所示步骤进行：
第一步骤是柱[5]芳烃S-I及S-II的制备：
将1,1-二溴代对苯二烷基醚A或B以及磁子加入三口烧瓶中，在氮气环境下加入1,2-二氯乙烷，剧烈搅拌30分钟后，将三颈烧瓶移至低温反应浴槽中，于0℃下加入三氟化硼·乙醚溶液，10min后将三颈烧瓶移至25℃，反应2h；经TLC(展开剂为V石油醚:V二氯甲烷＝1:1)监测体系，确认原料A或B反应完全后，倒入含有甲醇的烧杯中，用布氏漏斗抽滤后得到固体，柱层析(展开剂V石油醚:V二氯甲烷＝2:1)，得到相应的柱[5]芳烃S-I或S-II；
第二步骤是吡啶功能化水溶性柱[5]芳烃I或II的制备：
向圆底烧瓶中加入柱[5]芳烃S-I或S-II与磁子，在氮气环境下加入无水吡啶，120℃下回流反应72h；待柱[5]芳烃S-I或S-II完全转化后将体系移出油浴锅，冷却至室温后有固体析出，用砂芯漏斗抽滤，得到的固体用少量二氯甲烷洗涤，最终得到吡啶功能化水溶性柱[5]芳烃I或II。
2.根据权利要求1所述的柱[5]芳烃S-I或S-II的制备方法，其中，所述1,1-二溴代对苯二烷基醚、多聚甲醛及三氟化硼乙醚的摩尔比为1.0:(2.0-3.0):1.0。
3.根据权利要求1所述的柱[5]芳烃S-I或S-II的制备方法，其中，所述甲醇的用量为：每1.0g 1,1-二溴代对苯二烷基醚A或B，加入20-36mL甲醇。
4.根据权利要求1所述的吡啶功能化水溶性柱[5]芳烃I或II的制备方法，其中，所述吡啶的用量为：每100.0mg柱[5]芳烃S-I或S-II，加入1.0-3.0mL吡啶。
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