CN114751831A - 一种脱氢枞胺氯盐及其制备方法和应用 - Google Patents
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Abstract
本发明属于脱氢枞胺衍生物领域，具体涉及一种脱氢枞胺氯盐及其制备方法和应用，所述脱氢枞胺氯盐结构如式Ⅰ所示：
本发明提供的脱氢枞胺氯盐，能制备成超分子水凝胶，且对D‑酒石酸和L‑酒石酸有手性识别能力。而且本发明的脱氢枞胺氯盐成盐简单，无需复杂的有机合成反应，操作简单，廉价易得。
Description
技术领域
本发明属于脱氢枞胺衍生物领域，具体涉及一种脱氢枞胺氯盐及其制备方法和应用。
背景技术
超分子水凝胶是小分子通过非共价键作用而交联的软性材料，其吸水能力来自于凝胶因子的亲水性官能团，分子间通过自组装生成的纳米纤维交联而成的三维网状结构使其能够保持固定形态。分子间氢键、离子键以及配位键等非共价键作用使超分子凝胶具有良好的响应性，可逆性、自愈性和生物相容性等特点，被广泛应用于生物医药、检测和智能材料等领域。超分子水凝胶的凝胶因子来源广泛，有氨基酸类、壳聚糖、海藻酸钠、胶原等天然材料，也有丙烯酰胺、N-异丙烯基丙烯酰胺等人工合成材料。脱氢枞胺是从天然产物松香的改性产品之一，具有一定的生物活性，在杀菌、医药等领域具有着重要用途，但尚未有脱氢枞胺氯盐及其超分子水凝胶对酒石酸有手性识别能力的报道。
发明内容
本发明旨在解决上述技术问题，提供一种脱氢枞胺氯盐及其制备方法。
本发明的技术方案为：
一种脱氢枞胺氯盐，所述脱氢枞胺氯盐结构如式Ⅰ所示：
一种制备上述的脱氢枞胺氯盐的方法，包括以下步骤：
取脱氢枞胺溶于乙醇中，升温至60-70℃，回流冷凝，边搅拌边向其滴加盐酸水溶液直到pH为4，反应20-60min后向其中加入乙酸乙酯，停止加热，待反应液冷却后晶体完全析出，过滤得到脱氢枞胺氯盐粗产品，接着用乙醇和乙酸乙酯混合溶液重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐备用。
进一步地，包括以下步骤：
取0.01mol的脱氢枞胺溶于10-20mL乙醇中，升温至60-70℃，回流冷凝，边搅拌边向其滴加质量百分比为10％的盐酸水溶液直到pH为4，反应20-60min后向其中加入50-80mL乙酸乙酯，停止加热，待反应液冷却后晶体完全析出，过滤得到脱氢枞胺氯盐粗产品，接着用乙醇和乙酸乙酯混合溶液重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐备用。
优选地，所述乙醇和乙酸乙酯混合溶液中，乙醇和乙酸乙酯的体积比为1:10。
本发明所述的脱氢枞胺氯盐在制备超分子水凝胶中的应用，包括以下步骤：将式Ⅰ的脱氢枞胺氯盐溶于70-90℃的去离子水中，配制浓度为2mg/mL至60mg/mL的脱氢枞胺氯盐水溶液，冷却至室温得不同浓度的脱氢枞胺氯盐水凝胶。
本发明所述的脱氢枞胺氯盐在酒石酸的可视化手性识别中的应用，包括以下步骤：将脱氢枞胺氯盐溶于水中，向其中加入D-酒石酸或L-酒石酸，升温至80℃，待其溶解澄清后，置于40℃的水浴锅中；加入D-酒石酸的脱氢枞胺氯盐水溶液在一分钟内形成白色浑浊溶胶态的不透明溶液，随后溶液增稠呈浆糊状；加入L-酒石酸的脱氢枞胺氯盐水溶液在半小时内没有变化，随后有白色沉淀析出。
优选地，包括以下步骤：将0.03g脱氢枞胺氯盐溶于2ml水中，向其中加入D-酒石酸或L-酒石酸，升温至80℃，待其溶解澄清后，置于40℃的水浴锅中；加入D-酒石酸的脱氢枞胺氯盐水溶液在一分钟内形成白色浑浊溶胶态的不透明溶液，随后溶液增稠呈浆糊状；加入L-酒石酸的脱氢枞胺氯盐水溶液在半小时内没有变化，随后有白色沉淀析出。
本发明的有益效果为：
与现有技术比较，本发明的提供的脱氢枞胺氯盐，能制备成超分子水凝胶，且对D-酒石酸和L-酒石酸有手性识别能力。而且本发明的脱氢枞胺氯盐成盐简单，无需复杂的有机合成反应，操作简单，廉价易得。
附图说明
图1是本发明式Ⅰ的脱氢枞胺氯盐的核磁共振C谱图；
图2是本发明式Ⅰ的脱氢枞胺氯盐的核磁共振H谱图；
图3为本发明的脱氢枞胺氯盐水凝胶宏观图；
图4是实施例1中D-酒石酸与[DAA]Cl混合水溶液((a)及其L-酒石酸与[DAA]Cl混合水溶液(b)。
具体实施方式
下面将对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1式Ⅰ的脱氢枞胺氯盐制备
取2.85g脱氢枞胺(0.01mol)溶于15ml乙醇中，连接好回流装置升温至70℃，边磁力搅拌边向其滴加质量百分比为10％的盐酸水溶液直到pH为4，反应30min后向其中加入60mL乙酸乙酯，停止加热待反应液冷却后晶体完全析出，过滤得到的脱氢枞胺氯盐粗产品用乙醇和乙酸乙酯混合溶液(所述乙醇和乙酸乙酯混合溶液中，乙醇和乙酸乙酯的体积比为1:10)重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐固体备用。
核磁共振的结果如图1-2所示，且分析如下：1H NMR(500MHz,Methanol-d4)δ7.15(d,J＝8.2Hz,1H,H-11),6.95(dd,J＝8.3,2.1Hz,1H,H-12),6.86(d,J＝2.0Hz,1H,H-14),2.97–2.88(m,3H,H-18α,H-7),2.85–2.73(m,2H,H-18β,H-15),2.39–2.32(m,1H,H-1α),1.90–1.71(m,3H,H-5,6),1.69–1.29(m,5H,H-2,3,H-1β),1.23(s,3H,H-20),1.18(d,J＝6.9Hz,6H,H-16,17),1.08(s,3H,H-19).13C NMR(126MHz,Methanol-d4)δ146.53(C-9),145.66(C-13),134.07(C-8),126.31(C-14),123.71(C-11),123.55(C-12),50.60(C-18),46.14(C-5),37.85(C-1),37.24(C-10),35.55(C-4),35.05(C-3),33.44(C-15),29.23(C-7),24.17(C-20),23.13(C-16),23.12(C-17),18.64(C-6),17.96(C-2),16.80(C-19).
实施例2
取2.85g脱氢枞胺(0.01mol)溶于10ml乙醇中，连接好回流装置升温至60℃，边磁力搅拌边向其滴加质量百分比为10％的盐酸水溶液直到pH为4，反应20min后向其中加入50mL乙酸乙酯，停止加热待反应液冷却后晶体完全析出，过滤得到的脱氢枞胺氯盐粗产品用乙醇和乙酸乙酯混合溶液(所述乙醇和乙酸乙酯混合溶液中，乙醇和乙酸乙酯的体积比为1:10)重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐固体备用。
实施例3
取2.85g脱氢枞胺(0.01mol)溶于20ml乙醇中，连接好回流装置升温至65℃，边磁力搅拌边向其滴加质量百分比为10％的盐酸水溶液直到pH为4，反应60min后向其中加入80mL乙酸乙酯，停止加热待反应液冷却后晶体完全析出，过滤得到的脱氢枞胺氯盐粗产品用乙醇和乙酸乙酯混合溶液(所述乙醇和乙酸乙酯混合溶液中，乙醇和乙酸乙酯的体积比为1:10)重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐固体备用。
实施例4脱氢枞胺氯盐水凝胶的制备
将一定量的脱氢枞胺氯盐溶于80℃的去离子水中，配制浓度为2mg/mL的脱氢枞胺氯盐水溶液，冷却至室温得脱氢枞胺氯盐水凝胶。
该凝胶加热溶解为液体，冷却至室温重新形成水凝胶，具有良好的可重复性。
实施例5脱氢枞胺氯盐水凝胶的制备
将一定量的脱氢枞胺氯盐溶于80℃的去离子水中，配制浓度为60mg/mL的脱氢枞胺氯盐水溶液，冷却至室温得脱氢枞胺氯盐水凝胶(如图3所示)。
该凝胶加热溶解为液体，冷却至室温重新形成水凝胶，具有良好的可重复性。
实施例6酒石酸的可视化手性识别的方法
将0.03g脱氢枞胺氯盐([DAA]Cl)溶于2ml水中，向其中分别加入0.01gD-酒石酸和L-酒石酸，升温至80℃，待其溶解澄清后，将两者置于40℃的水浴锅中。加入D-酒石酸的脱氢枞胺氯盐水溶液在一分钟内形成白色浑浊溶胶态的不透明溶液，随后溶液增稠呈浆糊状；加入L-酒石酸的脱氢枞胺氯盐水溶液在半小时内没有变化，随后有白色沉淀析出(如图4所示)。两者析出方式的不同表明[DAA]Cl对D-酒石酸和L-酒石酸有手性识别能力。
上述说明是针对发明较佳可行实施例的详细说明，但实施例并非用以限定本发明的专利申请范围，凡本发明所提示的技术精神下所完成的同等变化或修饰变更，均应属于本发明所涵盖专利范围。
Claims (7)
1.一种脱氢枞胺氯盐，其特征在于，所述脱氢枞胺氯盐结构如式Ⅰ所示：
2.一种权利要求1所述的脱氢枞胺氯盐的制备方法，其特征在于，包括以下步骤：
取脱氢枞胺溶于乙醇中，升温至60-70℃，回流冷凝，边搅拌边向其滴加盐酸水溶液直到pH为4，反应20-60min后向其中加入乙酸乙酯，停止加热，待反应液冷却后晶体完全析出，过滤得到脱氢枞胺氯盐粗产品，接着用乙醇和乙酸乙酯混合溶液重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐备用。
3.如权利要求2所述的脱氢枞胺氯盐的制备方法，其特征在于，包括以下步骤：
取0.01mol的脱氢枞胺溶于10-20mL乙醇中，升温至60-70℃，回流冷凝，边搅拌边向其滴加质量百分比为10％的盐酸水溶液直到pH为4，反应20-60min后向其中加入50-80mL乙酸乙酯，停止加热，待反应液冷却后晶体完全析出，过滤得到脱氢枞胺氯盐粗产品，接着用乙醇和乙酸乙酯混合溶液重结晶，过滤干燥得到式Ⅰ的脱氢枞胺氯盐备用。
4.如权利要求2或3所述的脱氢枞胺氯盐的制备方法，其特征在于，所述乙醇和乙酸乙酯混合溶液中，乙醇和乙酸乙酯的体积比为1:10。
5.权利要求1所述的脱氢枞胺氯盐在制备超分子水凝胶中的应用，其特征在于，包括以下步骤：将式Ⅰ的脱氢枞胺氯盐溶于70-90℃的去离子水中，配制浓度为2mg/mL至60mg/mL的脱氢枞胺氯盐水溶液，冷却至室温得不同浓度的脱氢枞胺氯盐水凝胶。
6.权利要求1所述的脱氢枞胺氯盐在酒石酸的可视化手性识别中的应用，其特征在于，包括以下步骤：将脱氢枞胺氯盐溶于水中，向其中加入D-酒石酸或L-酒石酸，升温至80℃，待其溶解澄清后，置于40℃的水浴锅中；加入D-酒石酸的脱氢枞胺氯盐水溶液在一分钟内形成白色浑浊溶胶态的不透明溶液，随后溶液增稠呈浆糊状；加入L-酒石酸的脱氢枞胺氯盐水溶液在半小时内没有变化，随后有白色沉淀析出。
7.如权利要求6所述的应用，其特征在于，包括以下步骤：将0.03g脱氢枞胺氯盐溶于2ml水中，向其中加入D-酒石酸或L-酒石酸，升温至80℃，待其溶解澄清后，置于40℃的水浴锅中；加入D-酒石酸的脱氢枞胺氯盐水溶液在一分钟内形成白色浑浊溶胶态的不透明溶液，随后溶液增稠呈浆糊状；加入L-酒石酸的脱氢枞胺氯盐水溶液在半小时内没有变化，随后有白色沉淀析出。
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