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CN115057832A - 酰腙衍生物及其制备方法和应用 - Google Patents

酰腙衍生物及其制备方法和应用 Download PDF

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CN115057832A
CN115057832A CN202210521275.4A CN202210521275A CN115057832A CN 115057832 A CN115057832 A CN 115057832A CN 202210521275 A CN202210521275 A CN 202210521275A CN 115057832 A CN115057832 A CN 115057832A
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赵圣铭
韦珏
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Abstract

本发明酰腙衍生物结构如式Ⅰ所示，其制备方法具体包括以下步骤：（1）将式Ⅱ化合物溶于醇中，滴加浓硫酸后加热至90‑120℃，反应3‑6小时，得到式Ⅲ化合物；（2）将式Ⅲ化合物溶于乙醇，加入水合肼，加热至回流反应12‑16小时，得到式Ⅳ化合物；（3）将等摩尔量的式Ⅳ化合物和式Ⅴ化合物溶解于乙醇，加热至回流反应3小时，得到式Ⅰ化合物；本发明材料可以对多种外部刺激做出响应，而表现出宏观相态或者颜色的变化，同时具有抗菌效果。

Description

酰腙衍生物及其制备方法和应用
技术领域
本发明属于有机合成技术领域，具体涉及一种酰腙衍生物及其制备方法和应用。
背景技术
腙类类化合物具有多种多样的生物活性，如具有抗肿瘤、抗菌、抗炎、抗糖尿病和抗结核等广谱的生物活性。一些腙类类化合物已经发展成为商品化的农药，如日本武田药品工业公司开发的嘧啶腙杀菌剂 (Blasin)，主要防治水稻上的稻尾孢，稻长孺孢和稻梨孢等病原菌引起的病害如稻瘟病
酰腙类化合物还具有离子识别性能，具有与金属离子形成络合物的优异能力；近年来研究发现, 酰腙类化合物可作为识别阴离子的探针，并具有高选择性和灵敏度。设计并开发出系列以酰腙基团为基本单元的智能响应发光材料并同时具有抗菌效果，包括苯基上含有不同取代基的酰腙衍生物和含有不同荧光基团的酰腙衍生物，通过调控分子结构、分子间相互作用、环境条件，系统研究分子结构与性能的关系，获得具有智能响应性的发光材料，其中具有多刺激响应性质多重刺激响应发光材料由于它们的结构可调性和功能可控性而备受关注。
发明内容
为解决上述问题，本发明公开了一种酰腙衍生物及其制备方法和应用。这些材料可以对多种外部刺激做出响应，而表现出宏观相态或者颜色的变化，同时具有抗菌效果。本发明以酰腙为基本构筑基元，含有不同类型荧光基元、不同类型取代基的酰腙衍生物。
为达到上述目的，本发明的技术方案如下：
本发明提供一种酰腙衍生物，结构如式Ⅰ所示；
Figure RE-491536DEST_PATH_IMAGE001
式Ⅰ
其中，R1为H、OH、OR8或NO2；R8为C1-C6的烷基；
R3为H或OH；
R7为OH或H；
R4为H或OH；
R5为H、OH、
Figure RE-417904DEST_PATH_IMAGE002
或
Figure RE-DEST_PATH_IMAGE003
；
R6为H或OH。
本发明提供一种如上述的酰腙衍生物的制备方法，包括以下步骤：
（1）将式Ⅱ化合物溶于醇中，滴加浓硫酸后加热至90-120℃，反应3-6小时，得到式Ⅲ化合物；其中式Ⅲ化合物中R2为OCH3、OC2H5或OC3H7；
Figure RE-169959DEST_PATH_IMAGE004
式Ⅱ 式Ⅲ；
（2）将式Ⅲ化合物溶于乙醇，加入水合肼，加热至回流反应12-16小时，得到式Ⅳ化合物；
Figure RE-195684DEST_PATH_IMAGE005
式Ⅲ 式Ⅳ；
（3）将等摩尔量的式Ⅳ化合物和式Ⅴ化合物溶解于乙醇，加热至回流反应3小时，得到式Ⅰ化合物；
Figure RE-869242DEST_PATH_IMAGE006
式Ⅳ 式Ⅴ 式Ⅰ。
进一步地，步骤（1）中，式Ⅱ化合物与醇的摩尔体积比为1～2mol/L。
进一步地，步骤（2）中，式Ⅲ化合物与乙醇的摩尔体积比为2～3 mol/L。
进一步地，步骤（3）中，式Ⅳ化合物与乙醇的摩尔体积比为为0.1-0.5mol/L。
本发明还提供一种如上所述的酰腙衍生物在制备抗菌药物中的应用。
本发明还提供一种如上所述的酰腙衍生物在制备发光材料中的应用。
本发明还提供一种如上所述制备方法制备的酰腙衍生物在制备抗菌药物中的应用。
本发明还提供一种如上所述制备方法制备的酰腙衍生物在制备发光材料中的应用
本发明的有益效果为：
本发明一种酰腙衍生物及其制备方法和应用，这些材料可以对多种外部刺激做出响应，而表现出宏观相态或者颜色的变化，同时具有抗菌效果。本发明以酰腙为基本构筑基元，含有不同类型荧光基元、不同类型取代基的酰腙衍生物。
具体实施方式
下面结合具体实施方式，进一步阐明本发明，应理解下述具体实施方式仅用于说明本发明而不用于限制本发明的范围。
实施例1
（1）将0.2mol式Ⅱ化合物溶于100mL醇中，滴加浓硫酸后加热至90-120℃，反应3-6小时，得到式Ⅲ化合物；
（2）将0.1mol式Ⅲ化合物溶于50mL乙醇，加入水合肼（60%）60mL，加热至回流反应12-16小时，得到式Ⅳ化合物；
（3）将等摩尔量的0.1mol式Ⅳ化合物和0.1mol式Ⅴ化合物溶解于1L乙醇，加热至回流反应3小时，得到式Ⅰ化合物。
其中，其中，R1为H；R2为OC2H5，R3为H；R7为OH；R4为H；R5为
Figure RE-599301DEST_PATH_IMAGE002
；
R6为H。
实施例2
（1）将0.1mol式Ⅱ化合物溶于100mL醇中，滴加浓硫酸后加热至90-120℃，反应3-6小时，得到式Ⅲ化合物；
（2）将0.1mol式Ⅲ化合物溶于50mL乙醇，加入水合肼（60%）60mL，加热至回流反应12-16小时，得到式Ⅳ化合物；
（3）将等摩尔量的0.3mol式Ⅳ化合物和0.3mol式Ⅴ化合物溶解于1L乙醇，加热至回流反应3小时，得到式Ⅰ化合物。
其中，R1为H；R2为OCH3；R3为OH；R7为H；R4为H；R5
Figure RE-674704DEST_PATH_IMAGE003
；R6为H。
实施例3
（1）将0.1mol式Ⅱ化合物溶于100mL醇中，滴加浓硫酸后加热至90-120℃，反应3-6小时，得到式Ⅲ化合物；
（2）将0.15mol式Ⅲ化合物溶于50mL乙醇，加入水合肼（80%）60mL，加热至回流反应12-16小时，得到式Ⅳ化合物；
（3）将等摩尔量的0.5mol式Ⅳ化合物和0.5mol式Ⅴ化合物溶解于1L乙醇，加热至回流反应3小时，得到式Ⅰ化合物。
其中，R1为OH；R2为OCH3；R3为H或OH；R7为OH；R4为H；R5为H；R6为H。
需要说明的是，以上内容仅仅说明了本发明的技术思想，不能以此限定本发明的保护范围，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以做出若干改进和润饰，这些改进和润饰均落入本发明权利要求书的保护范围之内。

Claims (9)

1.一种酰腙衍生物，其特征在于，结构如式Ⅰ所示；
Figure DEST_PATH_IMAGE002
式Ⅰ
其中，R1为H、OH、OR8或NO2；R8为C1-C6的烷基；
R3为H或OH；
R7为OH或H；
R4为H或OH；
R5为H、OH、
Figure DEST_PATH_IMAGE004
或
Figure DEST_PATH_IMAGE006
；
R6为H或OH。
2.一种如权利要求1所述的酰腙衍生物的制备方法，其特征在于，包括以下步骤：
（1）将式Ⅱ化合物溶于醇中，滴加浓硫酸后加热至90-120℃，反应3-6小时，得到式Ⅲ化合物；其中式Ⅲ化合物中R2为OCH3、OC2H5或OC3H7；
Figure DEST_PATH_IMAGE008
式Ⅱ 式Ⅲ；
（2）将式Ⅲ化合物溶于乙醇，加入水合肼，加热至回流反应12-16小时，得到式Ⅳ化合物；
Figure DEST_PATH_IMAGE010
式Ⅲ 式Ⅳ；
（3）将等摩尔量的式Ⅳ化合物和式Ⅴ化合物溶解于乙醇，加热至回流反应3小时，得到式Ⅰ化合物；
Figure DEST_PATH_IMAGE012
式Ⅳ 式Ⅴ 式Ⅰ。
3.根据权利要求2所述的一种酰腙衍生物的制备方法，其特征在于，步骤（1）中，式Ⅱ化合物与醇的摩尔体积比为1～2mol/L。
4.根据权利要求2所述的一种酰腙衍生物的制备方法，其特征在于，步骤（2）中，式Ⅲ化合物与乙醇的摩尔体积比为2～3 mol/L。
5.根据权利要求2所述的一种酰腙衍生物的制备方法，其特征在于，步骤（3）中，式Ⅳ化合物与乙醇的摩尔体积比为为0.1-0.5mol/L。
6.权利要求1所述的酰腙衍生物在制备抗菌药物中的应用。
7.权利要求1所述的酰腙衍生物在制备发光材料中的应用。
8.权利要求2-5所述制备方法制备的酰腙衍生物在制备抗菌药物中的应用。
9.权利要求2-5所述制备方法制备的酰腙衍生物在制备发光材料中的应用。
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