CN113912592B - 一种和厚朴酚并二氢呋喃酯类衍生物、制备方法及其应用 - Google Patents
一种和厚朴酚并二氢呋喃酯类衍生物、制备方法及其应用 Download PDFInfo
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- CN113912592B CN113912592B CN202111294111.4A CN202111294111A CN113912592B CN 113912592 B CN113912592 B CN 113912592B CN 202111294111 A CN202111294111 A CN 202111294111A CN 113912592 B CN113912592 B CN 113912592B
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- honokiol
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- dihydrofuran
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- VVOAZFWZEDHOOU-UHFFFAOYSA-N honokiol Natural products OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 title claims abstract description 58
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 title claims abstract description 56
- -1 Honokiol dihydrofuran ester Chemical class 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 16
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 12
- 241000273311 Aphis spiraecola Species 0.000 claims abstract description 8
- 239000000642 acaricide Substances 0.000 claims abstract description 7
- 239000002917 insecticide Substances 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 22
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
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- 238000000034 method Methods 0.000 claims description 9
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 7
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 5
- 241000238631 Hexapoda Species 0.000 claims description 4
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Abstract
本发明公开了一种和厚朴酚并二氢呋喃酯类衍生物、制备方法及其应用，所述和厚朴酚并二氢呋喃酯类衍生物的化学结构式如式(I)所示：其中：R1、R2选自氢、烷酰基、取代或非取代苯酰基、取代或非取代苄酰基、取代或非取代吡啶酰基或二茂铁酰基的一种。实验表明，部分和厚朴酚并二氢呋喃酯类衍生物72h杀螨活性较和厚朴酚有显著性提高，且部分衍生物72h杀螨活性与螺螨酯相当，有望用于制备高效、环保、低毒的植物源杀螨剂。此外本发明的化合物对苹果黄蚜具有较好杀虫活性，有望用于制备环保、低毒的植物源杀虫剂。
Description
技术领域
本发明属于有机合成技术领域，具体涉及一种和厚朴酚并二氢呋喃酯类衍生物、制备方法及其应用。
背景技术
和厚朴酚(Honokiol)是从传统中药厚朴当中提取得到的含有连苯酚结构的化合物，因其具有广泛的生物学活性而成为研究的热点。
和厚朴酚类衍生物在医药和农药方面具有多种生物活性。在医药方面，具有抗癌【Life Sci，2019，221，204-211】、抗氧化【Molecules，2010，15，6452-6465】、抗病毒【Bioorganic&Medicinal Chemistry Letters，2007，17，4428-4431】、抗微生物【Researchin Microbiology，2017，168，626-635】和抗炎【Journal of Neuroimmunology，2018，323，78-86】等活性。在农药方面，具有杀虫活性【Industrial Crops and Products，2015，76，761-767】。
发明内容
针对上述现有技术不足与缺陷，本发明的目的在于，提供一种和厚朴酚并二氢呋喃酯类衍生物、制备方法及其应用。
为了达到上述目的，本申请采用如下技术方案予以实现：本发明提供一种和厚朴酚并二氢呋喃酯类衍生物，化学结构式如下式所示：
其中：R1、R2选自氢、烷酰基、取代或非取代苯酰基、取代或非取代苄酰基、取代或非取代吡啶酰基或二茂铁酰基的一种。
所述的和厚朴酚并二氢呋喃酯类衍生物具有以下结构之一：
(1)R1＝COPh；R2＝H
(2)R1＝CO(4-F)-Ph；R2＝H
(3)R1＝CO(4-Cl)-Ph；R2＝H
(4)R1＝CO(4-Br)-Ph；R2＝H
(5)R1＝CO(4-NO2)-Ph；R2＝H
(6)R1＝CO(4-OCH3)-Ph；R2＝H
(7)R1＝CO(4-CH3)-Ph；R2＝H
(8)R1＝COCH2Ph；R2＝H
(9)R1＝COCH2-(4-F)-Ph；R2＝H
(10)R1＝COCH2-(4-Cl)-Ph；R2＝H
(11)R1＝CO(2-Cl)-Py；R2＝H
(12)R1＝CO(2-OCH3)-Py；R2＝H
(13)R1＝COFerrocene；R2＝H
(14)R1＝COCH3；R2＝H
(15)R1＝CO(CH2)2CH3；R2＝H
(16)R1＝CO(CH2)4CH3；R2＝H
(17)R1＝CO(CH2)6CH3；R2＝H
(18)R1＝CO(CH2)10CH3；R2＝H
(19)R1＝CO(CH2)12CH3；R2＝H
(20)R1＝CO(CH2)14CH3；R2＝H
(21)R1＝CO(CH2)16CH3；R2＝H
(22)R1＝CO(CH2)11CH3；R2＝H
(23)R1＝CO(CH2)13CH3；R2＝H
(24)R1＝COPh；R2＝COPh
(25)R1＝CO(4-F)-Ph；R2＝CO(4-F)-Ph
(26)R1＝CO(4-Cl)-Ph；R2＝CO(4-Cl)-Ph
(27)R1＝CO(3-Cl)-Ph；R2＝CO(3-Cl)-Ph
(28)R1＝CO(4-Br)-Ph；R2＝CO(4-Br)-Ph
(29)R1＝CO(4-NO2)-Ph；R2＝CO(4-NO2)-Ph
(30)R1＝CO(4-OCH3)-Ph；R2＝CO(4-OCH3)-Ph
(31)R1＝CO(4-CH3)-Ph；R2＝CO(4-CH3)-Ph
(32)R1＝COCH2Ph；R2＝COCH2Ph
(33)R1＝COCH2-(4-F)-Ph；R2＝COCH2-(4-F)-Ph
(34)R1＝COCH2-(4-Cl)-Ph；R2＝COCH2-(4-Cl)-Ph
(35)R1＝COCH2-(4-OCH3)-Ph；R2＝COCH2-(4-OCH3)-Ph
(36)R1＝COPy；R2＝COPy
(37)R1＝CO(2-F)-Py；R2＝CO(2-F)-Py
(38)R1＝CO(6-F)-Py；R2＝CO(6-F)-Py
(39)R1＝CO(6-Cl)-Py；R2＝CO(6-Cl)-Py
(40)R1＝CO(2-OCH3)-Py；R2＝CO(2-OCH3)-Py
(41)R1＝CO(6-OCH3)-Py；R2＝CO(6-OCH3)-Py
(42)R1＝COFerrocene；R2＝COFerrocene
(43)R1＝COCH3；R2＝COCH3
(44)R1＝CO(CH2)2CH3；R2＝CO(CH2)2CH3
(45)R1＝CO(CH2)4CH3；R2＝CO(CH2)4CH3
(46)R1＝CO(CH2)6CH3；R2＝CO(CH2)6CH3
(47)R1＝CO(CH2)10CH3；R2＝CO(CH2)10CH3
(48)R1＝CO(CH2)12CH3；R2＝CO(CH2)12CH3
(49)R1＝CO(CH2)14CH3；R2＝CO(CH2)14CH3
(50)R1＝CO(CH2)16CH3；R2＝CO(CH2)16CH3
(51)R1＝CO(CH2)11CH3；R2＝CO(CH2)11CH3
(52)R1＝CO(CH2)13CH3；R2＝CO(CH2)13CH3
本发明的另一目的是提供上述和厚朴酚并二氢呋喃酯类衍生物的制备方法，包括如下步骤：
步骤1：向和厚朴酚中加入间氯过氧苯甲酸和碳酸钾反应制得中间体b；
步骤2：将步骤1制得的中间体b与取代羧酸反应，得到式(I)所示化合物。
具体的，步骤1包括将和厚朴酚和间氯过氧苯甲酸在二氯甲烷中进行反应后除去二氯甲烷，然后加入碳酸钾并在甲醇中反应，反应温度为20～30℃。
可选的，步骤2包括将中间体b与取代羧酸在无水二氯甲烷中反应，同时加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和4-二甲氨基吡啶，反应温度为20～30℃。
进一步的，步骤2中取代羧酸选自PhCOOH、(4-F)-PhCOOH、(3-Cl)-PhCOOH、(4-Cl)-PhCOOH、(4-Br)-PhCOOH、(4-NO2)-PhCOOH、(4-OCH3)-PhCOOH、(4-CH3)-PhCOOH、PhCH2COOH、(4-F)-Ph-CH2COOH、(4-Cl)-Ph-CH2COOH、(4-OCH3)-Ph-CH2COOH、2-氯烟酸、烟酸、2-氟烟酸、6-氟烟酸、6-氯烟酸、2-甲氧烟酸、6-甲氧烟酸、二茂铁甲酸、CH3COOH、CH3(CH2)2COOH、CH3(CH2)4COOH、CH3(CH2)6COOH、CH3(CH2)10COOH、CH3(CH2)12COOH、CH3(CH2)14COOH、CH3(CH2)16COOH、CH3(CH2)11COOH、CH3(CH2)13COOH中的一种。
本发明所述的和厚朴酚并二氢呋喃酯类衍生物用于制备杀虫剂的应用。
本发明所述的和厚朴酚并二氢呋喃酯类衍生物用于制备杀螨剂的应用
本发明所述和厚朴酚并二氢呋喃酯类衍生物的制备方法制备的和厚朴酚并二氢呋喃酯类衍生物用于制备杀虫剂的应用。
本发明所述和厚朴酚并二氢呋喃酯类衍生物的制备方法制备的和厚朴酚并二氢呋喃酯类衍生物用于制备杀螨剂的应用。
本发明与现有技术相比，有益的技术效果是：
本发明的和厚朴酚并二氢呋喃酯类衍生物制备方法简单，可以用于制备杀虫剂，其中杀虫剂包括杀螨剂，害虫包括农业上常见的蚜虫，比如常见的苹果黄蚜。所述的螨指农业常见的螨，例如的朱砂叶螨、二斑叶螨等。该系列厚朴酚并二氢呋喃酯类衍生物的结构通式(I)所示，R1、R2选自氢、烷酰基、取代或非取代苯酰基、取代或非取代苄酰基、取代或非取代吡啶酰基或二茂铁酰基的一种。经实验表明：该系列和厚朴酚并二氢呋喃酯类衍生物中部分衍生物对苹果黄蚜和朱砂叶螨具有较好的毒杀活性，相对母体和厚朴酚，活性显著提高，故有望用于制备高效、环保、低毒的植物源杀虫/螨剂。
附图说明
图1为化合物17的核磁共振氢谱谱图；
图2为化合物17的红外谱图；
图3为化合物31的核磁共振氢谱谱图；
图4为化合物31的红外谱图；
以下结合附图和实施例对本发明的具体内容作进一步详细解释说明。
具体实施方式
以下给出本发明的具体实施例，需要说明的是本发明并不局限于以下具体实施例，凡在本申请技术方案基础上做的等同变换均落入本发明的保护范围。
本发明的和厚朴酚并二氢呋喃酯类衍生物的制备方法，包括如下步骤：
步骤1：向和厚朴酚中加入间氯过氧苯甲酸和碳酸钾反应制得中间体b；
步骤2：将步骤1制得的中间体b与取代羧酸反应，得到式(I)所示化合物。
其中，步骤1包括将和厚朴酚和间氯过氧苯甲酸在二氯甲烷中进行反应后除去二氯甲烷，然后加入碳酸钾并在甲醇中反应，反应温度为20～30℃。
步骤2包括将中间体b与取代羧酸在无水二氯甲烷中反应，同时加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和4-二甲氨基吡啶，反应温度为20～30℃。
因此，本发明和厚朴酚并二氢呋喃酯类衍生物的合成路线可以如下：
依据上述合成路线：
首先将适量和厚朴酚溶于DCM中，加入m-CPBA，待和厚朴酚消耗完，除去DCM，加入甲醇和碳酸钾反应制得中间体b；
接着将适量中间体b与取代羧酸在合适反应体系(如存在1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC)、4-二甲氨基吡啶(DMAP)和无水二氯甲烷的反应体系)和反应条件(如反应温度为20-30℃)下反应制得本发明的衍生物。
在本发明中，m-CPBA是指间氯过氧苯甲酸；DCM是指二氯甲烷；EDC是指1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐；DMAP是指4-二甲氨基吡啶；
所述取代羧酸选自PhCOOH、(4-F)-PhCOOH、(3-Cl)-PhCOOH、(4-Cl)-PhCOOH、(4-Br)-PhCOOH、(4-NO2)-PhCOOH、(4-OCH3)-PhCOOH、(4-CH3)-PhCOOH、PhCH2COOH、(4-F)-Ph-CH2COOH、(4-Cl)-Ph-CH2COOH、(4-OCH3)-Ph-CH2COOH、2-氯烟酸、烟酸、2-氟烟酸、6-氟烟酸、6-氯烟酸、2-甲氧烟酸、6-甲氧烟酸、二茂铁甲酸、CH3COOH、CH3(CH2)2COOH、CH3(CH2)4COOH、CH3(CH2)6COOH、CH3(CH2)10COOH、CH3(CH2)12COOH、CH3(CH2)14COOH、CH3(CH2)16COOH、CH3(CH2)11COOH、CH3(CH2)13COOH中的一种。
以下给出制备和厚朴酚并二氢呋喃酯类衍生物1-52化合物的实施例。
实施例1：化合物17的制备方法：
结合图1化合物17的核磁共振氢谱谱图和图2化合物17的红外谱图；本实施例给出化合物17的制备方法：
步骤1：称取1mmol和厚朴酚，2.5mmol m-CPBA溶于10mL DCM中，在室温下搅拌6小时，待和厚朴酚消耗完后除去DCM，加入20mL甲醇和3mmol碳酸钾，室温搅拌12小时，TLC检测；反应完全后除去甲醇，用DCM(20mL×3)萃取，合并有机相，干燥，浓缩，柱层析分离，得中间体b，产率37％；
步骤2：将中间体b(0.5mmol)、对正辛酸(0.6mmol)，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC,0.6mmol)和4-二甲氨基吡啶(DMAP,0.06mmol)在5mL无水二氯甲烷中，室温搅拌8h；反应完全后加入30mL乙酸乙酯稀释，再依次加入15mL 0.1M盐酸水溶液，5％碳酸氢钠水溶液和饱和食盐水洗涤，有机相干燥浓缩，薄层层析分离得化合物17(138.0mg白色固体，产率65％)。
实施例2：化合物31的制备方法：
结合图3化合物31的核磁共振氢谱谱图和图4化合物31的红外谱图；本实施例给出化合物31的制备方法：
步骤1实施例1相同；
步骤2：将中间体b(0.5mmol)、对甲基苯甲酸(1.25mmol)，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC,1.25mmol)和4-二甲氨基吡啶(DMAP,0.125mmol)在5mL无水二氯甲烷中，室温搅拌8h；反应完全后加入30mL乙酸乙酯稀释，再依次加入15mL 0.1M盐酸水溶液，5％碳酸氢钠水溶液和饱和食盐水洗涤，有机相干燥浓缩，薄层层析分离得化合物31(61.5mg白色固体，产率23％)。
实施例3：化合物1-16、18-30、32-52的制备方法：
遵循本发明的制备路线，参考上述化合物17和31的制备方法，采取合适的制备条件制备化合物1-16、18-30、32-52。具体制备方法为本领域技术人员在本发明公开范围内可获得，此处不再赘述。
上述制备方法制备得到的化合物1～化合物52具有以下通式，且分别对应具有(1)～(52)的结构的化合物：
其中：R1、R2选自氢、烷酰基、取代或非取代苯酰基、取代或非取代苄酰基、取代或非取代吡啶酰基或二茂铁酰基的一种。
(1)R1＝COPh；R2＝H
(2)R1＝CO(4-F)-Ph；R2＝H
(3)R1＝CO(4-Cl)-Ph；R2＝H
(4)R1＝CO(4-Br)-Ph；R2＝H
(5)R1＝CO(4-NO2)-Ph；R2＝H
(6)R1＝CO(4-OCH3)-Ph；R2＝H
(7)R1＝CO(4-CH3)-Ph；R2＝H
(8)R1＝COCH2Ph；R2＝H
(9)R1＝COCH2-(4-F)-Ph；R2＝H
(10)R1＝COCH2-(4-Cl)-Ph；R2＝H
(11)R1＝CO(2-Cl)-Py；R2＝H
(12)R1＝CO(2-OCH3)-Py；R2＝H
(13)R1＝COFerrocene；R2＝H
(14)R1＝COCH3；R2＝H
(15)R1＝CO(CH2)2CH3；R2＝H
(16)R1＝CO(CH2)4CH3；R2＝H
(17)R1＝CO(CH2)6CH3；R2＝H
(18)R1＝CO(CH2)10CH3；R2＝H
(19)R1＝CO(CH2)12CH3；R2＝H
(20)R1＝CO(CH2)14CH3；R2＝H
(21)R1＝CO(CH2)16CH3；R2＝H
(22)R1＝CO(CH2)11CH3；R2＝H
(23)R1＝CO(CH2)13CH3；R2＝H
(24)R1＝COPh；R2＝COPh
(25)R1＝CO(4-F)-Ph；R2＝CO(4-F)-Ph
(26)R1＝CO(4-Cl)-Ph；R2＝CO(4-Cl)-Ph
(27)R1＝CO(3-Cl)-Ph；R2＝CO(3-Cl)-Ph
(28)R1＝CO(4-Br)-Ph；R2＝CO(4-Br)-Ph
(29)R1＝CO(4-NO2)-Ph；R2＝CO(4-NO2)-Ph
(30)R1＝CO(4-OCH3)-Ph；R2＝CO(4-OCH3)-Ph
(31)R1＝CO(4-CH3)-Ph；R2＝CO(4-CH3)-Ph
(32)R1＝COCH2Ph；R2＝COCH2Ph
(33)R1＝COCH2-(4-F)-Ph；R2＝COCH2-(4-F)-Ph
(34)R1＝COCH2-(4-Cl)-Ph；R2＝COCH2-(4-Cl)-Ph
(35)R1＝COCH2-(4-OCH3)-Ph；R2＝COCH2-(4-OCH3)-Ph
(36)R1＝COPy；R2＝COPy
(37)R1＝CO(2-F)-Py；R2＝CO(2-F)-Py
(38)R1＝CO(6-F)-Py；R2＝CO(6-F)-Py
(39)R1＝CO(6-Cl)-Py；R2＝CO(6-Cl)-Py
(40)R1＝CO(2-OCH3)-Py；R2＝CO(2-OCH3)-Py
(41)R1＝CO(6-OCH3)-Py；R2＝CO(6-OCH3)-Py
(42)R1＝COFerrocene；R2＝COFerrocene
(43)R1＝COCH3；R2＝COCH3
(44)R1＝CO(CH2)2CH3；R2＝CO(CH2)2CH3
(45)R1＝CO(CH2)4CH3；R2＝CO(CH2)4CH3
(46)R1＝CO(CH2)6CH3；R2＝CO(CH2)6CH3
(47)R1＝CO(CH2)10CH3；R2＝CO(CH2)10CH3
(48)R1＝CO(CH2)12CH3；R2＝CO(CH2)12CH3
(49)R1＝CO(CH2)14CH3；R2＝CO(CH2)14CH3
(50)R1＝CO(CH2)16CH3；R2＝CO(CH2)16CH3
(51)R1＝CO(CH2)11CH3；R2＝CO(CH2)11CH3
(52)R1＝CO(CH2)13CH3；R2＝CO(CH2)13CH3
在本发明的一种实施例中，所述的中间体b的理化性质如下：
1)淡黄色液体，收率76％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1718,1233,1197,819.1H NMR(500MHz,CDCl3)δ:7.26(s,1H,Ph-H),7.21(d,J＝8.0Hz,1H,Ph-H),7.11–7.09(m,1H,Ph-H),7.07(s,1H,Ph-H),6.92(dd,J＝13.0,8.0Hz,2H,Ph-H),5.12(s,1H,OH),5.00–4.95(m,1H,OCH),3.91–3.89(m,1H,COOCH2),3.80–3.75(m,1H,COOCH2),3.33–3.28(m,1H),3.16–3.07(m,2H),2.88–2.84(m,1H),2.80–2.75(m,2H),2.56(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C18H18O4Na([M+Na]+),321.1097；found,321.1097.
化合物1的理化性质如下：
1)淡黄色液体，收率66％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1729,1261,1188,749.1H NMR(500MHz,CDCl3)δ:8.05–8.03(m,2H,Ph-H),7.60–7.57(m,1H,Ph-H),7.46(t,J＝8.0Hz,2H,Ph-H),7.31(d,J＝2.0Hz,1H,Ph-H),7.28(d,J＝2.0Hz,2H,Ph-H),7.24–7.22(m,1H,Ph-H),7.21(d,J＝8.5Hz,1H,Ph-H),6.73(d,J＝8.5Hz,1H,Ph-H),4.90–4.85(m,1H,OCH),3.81–3.78(m,1H,OCH2),3.70–3.66(m,1H,OCH2),3.22–3.14(m,2H),2.98–2.86(m,3H),2.84(t,J＝5.0Hz,1H),2.61(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C25H22O5Na([M+Na]+),425.1359；found,425.1352.
化合物2的理化性质如下：
1)白色固体，熔点46-48℃，收率56％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1732,1264,1190,750.1H NMR(500MHz,CDCl3)δ:8.07–8.04(m,2H,Ph-H),7.31(d,J＝2.0Hz,1H,Ph-H),7.28–7.27(m,1H,Ph-H),7.24(s,1H,Ph-H),7.22–7.18(m,2H,Ph-H),7.13–7.10(m,2H,Ph-H),6.73(d,J＝8.0Hz,1H,Ph-H),4.91–4.86(m,1H,OCH),3.83–3.80(m,1H,OCH2),3.71–3.67(m,1H,OCH2),3.24–3.14(m,2H),2.97–2.87(m,3H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC25H21FO5Na([M+Na]+),443.1265；found,443.1254.
化合物3的理化性质如下：
1)淡黄色液体，收率47％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1732,1260,1188,745.1H NMR(500MHz,CDCl3)δ:7.98(d,J＝8.5Hz,2H,Ph-H),7.43(d,J＝8.5Hz,2H,Ph-H),7.31(d,J＝2.0Hz,1H,Ph-H),7.28(d,J＝2.0Hz,1H,Ph-H),7.24(s,1H,Ph-H),7.21(t,J＝8.5Hz,2H,Ph-H),6.73(d,J＝8.0Hz,1H,Ph-H),4.92–4.87(m,1H,OCH),3.84–3.80(m,1H,OCH2),3.72–3.67(m,1H,OCH2),3.22–3.15(m,2H),2.97–2.87(m,3H),2.85(t,J＝4.5Hz,1H),2.61(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcdfor C25H21ClO5Na([M+Na]+),459.0970；found,459.0957.
化合物4的理化性质如下：
1)白色固体，熔点48-51℃，收率33％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1731,1260,1187,742.1H NMR(500MHz,CDCl3)δ:7.90(d,J＝8.0Hz,2H,Ph-H),7.59(d,J＝8.0Hz,2H,Ph-H),7.30–7.27(m,2H,Ph-H),7.23–7.18(m,3H,Ph-H),6.72(d,J＝8.5Hz,1H,Ph-H),4.92–4.86(m,1H,OCH),3.82–3.80(m,1H,OCH2),3.71–3.67(m,1H,OCH2),3.20–3.15(m,2H),2.97–2.87(m,3H),2.84(t,J＝4.0Hz,1H),2.60–2.59(m,1H)；HRMS(ESI):calcd for C25H21BrO5Na([M+Na]+),503.0465；found,503.0445.
化合物5的理化性质如下：
1)淡黄色液体，收率25％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1737,1263,1188,819.1H NMR(400MHz,CDCl3)δ:8.31(d,J＝8.8Hz,2H,Ph-H),8.21(d,J＝8.8Hz,2H,Ph-H),7.33–7.28(m,2H,Ph-H),7.23–7.18(m,3H,Ph-H),6.73(d,J＝8.0Hz,1H,Ph-H),4.92–4.86(m,1H,OCH),3.85–3.81(m,1H,OCH2),3.71–3.67(m,1H,OCH2),3.23–3.15(m,2H),3.00–2.92(m,3H),2.85–2.83(m,1H),2.61(dd,J＝4.8,2.4Hz,1H)；HRMS(ESI):calcd for C25H21NO7Na([M+Na]+),470.1210；found,470.1212.
化合物6的理化性质如下：
1)白色固体，熔点47-50℃，收率12％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1725,1259,1190,755.1H NMR(500MHz,CDCl3)δ:8.00(d,J＝8.5Hz,2H,Ph-H),7.30–7.28(m,1H,Ph-H),7.26–7.22(m,3H,Ph-H),7.20–7.18(m,1H,Ph-H),6.92(d,J＝8.5Hz,2H,Ph-H),6.73(d,J＝8.5Hz,1H,Ph-H),4.91–4.85(m,1H,OCH),3.87(s,3H,Ph-CH3),3.81–3.79(m,1H,OCH2),3.71–3.67(m,1H,OCH2),3.22–3.14(m,2H),2.97–2.85(m,3H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C26H24O6Na([M+Na]+),455.1465；found,455.1472.
化合物7的理化性质如下：
1)淡黄色液体，收率38％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1729,1263,1186,741.1H NMR(500MHz,CDCl3)δ:7.93(d,J＝7.5Hz,2H,Ph-H),7.30(s,1H,Ph-H),7.26(s,1H,Ph-H),7.24–7.22(m,4H,Ph-H),7.20(d,J＝8.0Hz,1H,Ph-H),6.72(d,J＝8.5Hz,1H,Ph-H),4.90–4.85(m,1H,OCH),3.81–3.78(m,1H,OCH2),3.70–3.66(m,1H,OCH2),3.20–3.14(m,2H),2.97–2.85(m,3H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H),2.42(s,3H,Ph-CH3)；HRMS(ESI):calcd for C26H24O5Na([M+Na]+),439.1516；found,439.1508.
化合物8的理化性质如下：
1)淡黄色液体，收率27％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1751,1233,1191,826.1H NMR(500MHz,CDCl3)δ:7.28–7.27(m,3H,Ph-H),7.21–7.15(m,4H,Ph-H),7.12(s,1H,Ph-H),7.07(d,J＝8.0Hz,1H,Ph-H),7.02(d,J＝8.0Hz,1H,Ph-H),6.71(d,J＝8.5Hz,1H,Ph-H),4.96–4.91(m,1H,OCH),3.88–3.86(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.67(s,2H,CH2Ph),3.21–3.16(m,2H),2.99–2.95(m,1H),2.92–2.88(m,1H),2.85–2.79(m,2H),2.56(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC26H24O5Na([M+Na]+),439.1516；found,439.1512.
化合物9的理化性质如下：
1)淡黄色液体，收率26％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1752,1229,1193,826.1H NMR(500MHz,CDCl3)δ:7.21–7.19(m,2H,Ph-H),7.12–7.10(m,3H,Ph-H),7.06(dd,J＝18.0,8.0Hz,2H,Ph-H),6.98(t,J＝8.5Hz,2H,Ph-H),6.71(d,J＝8.5Hz,1H,Ph-H),4.97–4.92(m,1H,OCH),3.90–3.88(m,1H,OCH2),3.80–3.74(m,1H,OCH2),3.64(s,2H,CH2Ph),3.21–3.14(m,2H),3.01–2.96(m,1H),2.92–2.82(m,2H),2.81(t,J＝4.5Hz,1H),2.57(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC26H23FO5Na([M+Na]+),457.1422；found,457.1430.
化合物10的理化性质如下：
1)淡黄色液体，收率66％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1752,1233,1190,747.1H NMR(500MHz,CDCl3)δ:7.25–7.19(m,4H,Ph-H),7.08–7.00(m,5H,Ph-H),6.71(d,J＝8.5Hz,1H,Ph-H),4.98–4.93(m,1H,OCH),3.90–3.87(m,1H,OCH2),3.79–3.74(m,1H,OCH2),3.63(s,2H,CH2Ph),3.19–3.14(m,2H),2.99–2.95(m,1H),2.92–2.82(m,2H),2.81(t,J＝4.5Hz,1H),2.56(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C26H23ClO5Na([M+Na]+),473.1126；found,473.1135.
化合物11的理化性质如下：
1)白色固体，熔点59-61℃，收率16％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1746,1235,1186,751.1H NMR(500MHz,CDCl3)δ:8.53(dd,J＝4.5,2.0Hz,1H,Ar-H),8.02(dd,J＝7.5,2.0Hz,1H,Ar-H),7.32–7.28(m,3H,Ar-H),7.24–7.21(m,2H,Ar-H),7.20–7.18(m,1H,Ar-H),6.78(d,J＝8.5Hz,1H,Ar-H),4.95–4.90(m,1H,OCH),3.87–3.85(m,1H,OCH2),3.74–3.71(m,1H,OCH2),3.24–3.19(m,2H),3.02–2.98(m,1H),2.96–2.89(m,2H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C24H20ClNO5Na([M+Na]+),460.0922；found,460.0915.
化合物12的理化性质如下：
1)白色固体，熔点54-56℃，收率26％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1715,1235,1186,773.1H NMR(500MHz,CDCl3)δ:8.34(dd,J＝5.0,2.0Hz,1H,Ar-H),8.09(dd,J＝7.5,2.0Hz,1H,Ar-H),7.30–7.27(m,2H,Ar-H),7.25–7.23(m,2H,Ar-H),7.20(d,J＝8.0Hz,1H,Ar-H),6.94(dd,J＝7.5,5.0Hz,1H,Ar-H),6.76(d,J＝8.5Hz,1H,Ar-H),4.93–4.88(m,1H,OCH),4.03(s,3H,Ar-OCH3),3.85–3.82(m,1H,OCH2),3.73–3.69(m,1H,OCH2),3.22–3.17(m,2H),2.99–2.93(m,2H),2.90–2.86(m,1H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C25H23NO6Na([M+Na]+),456.1418；found,456.1421.
化合物13的理化性质如下：
1)黄色固体，熔点64-66℃，收率59％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1718,1234,1189,820.1H NMR(500MHz,CDCl3)δ:7.31–7.29(m,2H,Ph-H),7.25–7.23(m,2H,Ph-H),7.18(d,J＝8.0Hz,1H,Ph-H),6.86(d,J＝8.0Hz,1H,Ph-H),4.95–4.90(m,1H,OCH),4.81(s,2H,Ferrocene-H),4.42(s,2H,Ferrocene-H),4.03(s,5H,Ferrocene-H),3.85–3.82(m,1H,COOCH2),3.72–3.69(m,1H,COOCH2),3.30–3.25(m,1H),3.21–3.18(m,1H),3.08–3.03(m,1H),2.97–2.93(m,1H),2.88–2.82(m,2H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C29H26FeO5Na([M+Na]+),533.1022；found,533.1028.
化合物14的理化性质如下：
1)淡黄色液体，收率55％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1748,1225,1194,826.1H NMR(400MHz,CDCl3)δ:7.25(d,J＝2.4Hz,1H,Ph-H),7.23–7.20(m,2H,Ph-H),7.19–7.17(m,1H,Ph-H),7.05(d,J＝8.0Hz,1H,Ph-H),6.82(d,J＝8.4Hz,1H,Ph-H),4.99–4.93(m,1H,OCH),3.90–3.87(m,1H,OCH2),3.79–3.74(m,1H,OCH2),3.31–3.25(m,1H),3.20–3.15(m,1H),3.08–3.02(m,1H),2.94–2.89(m,1H),2.87–2.81(m,2H),2.59(dd,J＝4.8,2.4Hz,1H),2.11(s,3H,COOCH3)；HRMS(ESI):calcdfor C20H20O5Na([M+Na]+),363.1203；found,363.1211.
化合物15的理化性质如下：
1)淡黄色液体，收率45％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1751,1237,1187,828.1H NMR(400MHz,CDCl3)δ:7.24–7.20(m,3H,Ph-H),7.17–7.14(m,1H,Ph-H),7.04(d,J＝8.4Hz,1H,Ph-H),6.81(d,J＝8.4Hz,1H,Ph-H),4.99–4.92(m,1H,OCH),3.89–3.86(m,1H,OCH2),3.78–3.73(m,1H,OCH2),3.30–3.24(m,1H),3.20–3.15(m,1H),3.07–3.01(m,1H),2.95–2.89(m,1H),2.87–2.80(m,2H),2.58(dd,J＝4.8,2.8Hz,1H),2.36(t,J＝7.2Hz,2H,OCOCH2),1.64–1.55(m,2H,CH2),0.88(t,J＝7.6Hz,3H,CH3)；HRMS(ESI):calcd for C22H24O5Na([M+Na]+),391.1516；found,391.1526.
化合物16的理化性质如下：
1)淡黄色液体，收率78％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1752,1234,1192,827.1H NMR(400MHz,CDCl3)δ:7.24–7.15(m,4H,Ph-H),7.04(d,J＝7.2Hz,1H,Ph-H),6.80(d,J＝7.6Hz,1H,Ph-H),4.97–4.91(m,1H,OCH),3.88–3.74(m,2H,OCH2),3.29–3.17(m,2H),3.06–3.01(m,1H),2.94–2.81(m,3H),2.58–2.57(m,1H),2.37(t,J＝6.8Hz,2H,OCOCH2),1.57–1.54(m,2H,CH2),1.28–1.20(m,4H,2CH2),0.88(t,J＝6.0Hz,3H,CH3)；HRMS(ESI):calcd for C24H28O5Na([M+Na]+),419.1829；found,419.1838.
化合物17的理化性质如下：
1)淡黄色液体，收率65％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1752,1234,1192,828.1H NMR(400MHz,CDCl3)δ:7.24–7.20(m,3H,Ph-H),7.17(dd,J＝8.4,1.6Hz,1H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.4Hz,1H,Ph-H),4.98–4.92(m,1H,OCH),3.89–3.85(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.30–3.23(m,1H),3.20–3.15(m,1H),3.07–3.01(m,1H),2.94–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝4.8,2.8Hz,1H),2.38(t,J＝7.6Hz,2H,OCOCH2),1.59–1.51(m,2H,CH2),1.30–1.24(m,8H,4CH2),0.89(t,J＝6.8Hz,3H,CH3)；HRMS(ESI):calcd for C26H32O5Na([M+Na]+),447.2142；found,447.2152.
化合物18的理化性质如下：
1)淡黄色液体，收率55％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1754,1234,1191,827.1H NMR(400MHz,CDCl3)δ:7.24–7.20(m,3H,Ph-H),7.17(dd,J＝8.0,1.6Hz,1H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.4Hz,1H,Ph-H),4.98–4.92(m,1H,OCH),3.89–3.86(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.30–3.24(m,1H),3.20–3.15(m,1H),3.07–3.01(m,1H),2.95–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝4.8,2.8Hz,1H),2.37(t,J＝7.6Hz,2H,OCOCH2),1.58–1.53(m,2H,CH2),1.31–1.24(m,16H,8CH2),0.89(t,J＝6.4Hz,3H,CH3)；HRMS(ESI):calcd for C30H40O5Na([M+Na]+),503.2768；found,503.2776.
化合物19的理化性质如下：
1)淡黄色液体，收率53％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1754,1234,1191,827.1H NMR(400MHz,CDCl3)δ:7.24(m,1H,Ph-H),7.22–7.20(m,2H,Ph-H),7.17(dd,J＝8.0,1.6Hz,1H,Ph-H),7.04(d,J＝8.4Hz,1H,Ph-H),6.80(d,J＝8.4Hz,1H,Ph-H),4.98–4.92(m,1H,OCH),3.89–3.86(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.30–3.23(m,1H),3.20–3.15(m,1H),3.07–3.01(m,1H),2.95–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝4.8,2.8Hz,1H),2.37(t,J＝7.6Hz,2H,OCOCH2),1.57–1.53(m,2H,CH2),1.31–1.24(m,20H,10CH2),0.89(t,J＝6.8Hz,3H,CH3)；HRMS(ESI):calcd forC32H44O5Na([M+Na]+),531.3081；found,531.3090.
化合物20的理化性质如下：
1)淡黄色液体，收率76％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1755,1234,1191,827.1H NMR(500MHz,CDCl3)δ:7.39–7.20(m,3H,Ph-H),7.16(d,J＝8.0Hz,1H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.80(d,J＝8.5Hz,1H,Ph-H),4.97–4.92(m,1H,OCH),3.88–3.86(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.29–3.24(m,1H),3.17(s,1H),3.06–3.02(m,1H),2.94–2.81(m,3H),2.57(s,1H),2.36(t,J＝7.0Hz,2H,OCOCH2),1.56–1.55(m,2H,CH2),1.31–1.24(m,24H,12CH2),0.89(t,J＝6.0Hz,3H,CH3)；HRMS(ESI):calcd for C34H48O5Na([M+Na]+),559.3394；found,559.3389.
化合物21的理化性质如下：
1)白色固体，熔点34-35℃，收率44％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1750,1228,1197,836.1H NMR(500MHz,CDCl3)δ:7.23–7.20(m,3H,Ph-H),7.16(d,J＝8.0Hz,1H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.80(d,J＝8.0Hz,1H,Ph-H),4.97–4.92(t,J＝9.3Hz,1H,OCH),3.88–3.86(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.29–3.24(m,1H),3.17(s,1H),3.06–3.02(m,1H),2.94–2.90(m,1H),2.86–2.81(m,2H),2.58–2.57(m,1H),2.36(t,J＝7.0Hz,2H,OCOCH2),1.56–1.54(m,2H,CH2),1.31–1.25(s,28H,14CH2),0.89(t,J＝6.0Hz,3H,CH3)；HRMS(ESI):calcd for C36H52O5Na([M+Na]+),587.3707；found,587.3701.
化合物22的理化性质如下：
1)淡黄色液体，收率54％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1754,1234,1191,827.1H NMR(500MHz,CDCl3)δ:7.24–7.15(m,4H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.80(d,J＝8.0Hz,1H,Ph-H),4.97–4.92(m,1H,OCH),3.88–3.85(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.29–3.24(m,1H),3.19–3.25(m,1H),3.06–3.02(m,1H),2.94–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝5.0,2.5Hz,1H),2.37(t,J＝7.5Hz,2H,OCOCH2),1.56–1.53(m,2H,CH2),1.30–1.21(m,18H,9CH2),0.89(t,J＝6.0Hz,3H,CH3)；HRMS(ESI):calcd for C31H42O5Na([M+Na]+),517.2924；found,517.2937.
化合物23的理化性质如下：
1)淡黄色液体，收率48％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1754,1234,1191,827.1H NMR(500MHz,CDCl3)δ:7.23–7.15(m,4H,Ph-H),7.03(d,J＝8.5Hz,1H,Ph-H),6.80(d,J＝8.5Hz,1H,Ph-H),4.97–4.92(m,1H,OCH),3.88–3.85(m,1H,OCH2),3.78–3.74(m,1H,OCH2),3.29–3.24(m,1H),3.19–3.15(m,1H),3.06–3.00(m,1H),2.93–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝5.0,2.5Hz,1H),2.37(t,J＝7.5Hz,2H,OCOCH2),1.56–1.53(m,2H,CH2),1.31–1.20(m,22H,11CH2),0.89(t,J＝6.0Hz,3H,CH3)；HRMS(ESI):calcd for C33H46O5Na([M+Na]+)545.3237,；found,545.3262.
化合物24的理化性质如下：
1)淡黄色液体，收率40％；
2)该化合物的红外光谱图、核磁共振谱图特征：
IR cm-1(KBr):1725,1275,1190,737.1H NMR(500MHz,CDCl3)δ:7.83(m,2H,Ph-H),7.74–7.71(m,2H,Ph-H),7.37–7.27(m,10H,Ph-H),7.21(m,Ph-H),6.77(d,J＝8.0Hz,1H,Ph-H),5.13–5.07(m,1H,OCH),4.49–4.46(m 1H,COOCH2),4.43–4.40(m,1H,COOCH2),3.35–3.30(m,1H),3.22–3.19(m,1H),3.02–2.94(m,2H),2.90–2.83(m,2H),2.60(dd,J＝5.0,2.5Hz,1H).
化合物25的理化性质如下：
1)白色固体，熔点104-106℃，收率28％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1728,1270,1191,755.1H NMR(500MHz,CDCl3)δ:8.06(dd,J＝9.0,5.5Hz,2H,Ph-H),7.93(dd,J＝8.5,5.5Hz,2H,Ph-H),7.32(d,J＝2.0Hz,1H,Ph-H),7.29–7.26(m,2H,Ph-H),7.25–7.23(m,1H,Ph-H),7.20–7.19(m,1H,Ph-H),7.10–7.03(m,4H,Ph-H),6.76(d,J＝8.5Hz,1H,Ph-H),5.13–5.08(m,1H,OCH),4.52–4.49(m,1H,COOCH2),4.43–4.40(m,1H,COOCH2),3.36–3.31(m,1H),3.23–3.19(m,1H),3.03–2.98(m,1H),2.97–2.89(m,2H),2.85(t,J＝5.0Hz,1H),2.61(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC32H24F2O6Na([M+Na]+),565.1433；found,565.1426.
化合物26的理化性质如下：
1)白色固体，熔点92-94℃，收率28％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1727,1268,1187,748.1H NMR(500MHz,CDCl3)δ:7.96(d,J＝8.5Hz,2H,Ph-H),7.83(d,J＝8.0Hz,2H,Ph-H),7.40(d,J＝8.5Hz,2H,Ph-H),7.36(d,J＝8.5Hz,2H,Ph-H),7.31(d,J＝2.0Hz,1H,Ph-H),7.29–7.27(m,2H,Ph-H),7.25–7.23(m,1H,Ph-H),7.20(d,J＝8.5Hz,1H,Ph-H),6.76(d,J＝8.0Hz,1H,Ph-H),5.13–5.08(m,1H,OCH),4.52–4.49(m,1H,COOCH2),4.44–4.40(m,1H,COOCH2),3.36–3.31(m,1H),3.23–3.19(m,1H),3.03–2.99(m,1H),2.97–2.89(m,2H),2.85(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC32H24Cl2O6Na([M+Na]+),597.0842；found,597.0838.
化合物27的理化性质如下：
1)淡黄色液体，收率38％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1729,1247,1189,740.1H NMR(500MHz,CDCl3)δ:7.99(s,1H,Ph-H),7.89–7.88(m,2H,Ph-H),7.78(d,J＝8.0Hz,1H,Ph-H),7.53–7.49(m,2H,Ph-H),7.37–7.28(m,4H,Ph-H),7.27–7.26(m,1H,Ph-H),7.23–7.20(m,2H,Ph-H),6.78(d,J＝8.5Hz,1H,Ph-H),5.14–5.09(m,1H,OCH),4.52–4.49(m,1H,COOCH2),4.45–4.42(m,1H,COOCH2),3.39–3.34(m,1H),3.22–3.19(m,1H),3.05–3.01(m,1H),2.97–2.88(m,2H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C32H24Cl2O6Na([M+Na]+),597.0842；found,597.0829.
化合物28的理化性质如下：
1)白色固体，熔点65-67℃，收率19％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1725,1266,1185,745.1H NMR(500MHz,CDCl3)δ:7.89(d,J＝8.5
Hz,2H,Ph-H),7.75(d,J＝8.0Hz,2H,Ph-H),7.57(d,J＝8.5Hz,2H,Ph-H),7.53(d,J＝8.5Hz,2H,Ph-H),7.31(d,J＝2.0Hz,1H,Ph-H),7.29–7.27(m,2H,Ph-H),7.24–7.22(m,1H,Ph-H),7.20(d,J＝8.0Hz,1H,Ph-H),6.75(d,J＝8.5Hz,1H,Ph-H),5.13–5.08(m,1H,OCH),4.52–4.49(m,1H,COOCH2),4.44–4.40(m,1H,COOCH2),3.37–3.31(m,1H),3.23–3.20(m,1H),3.03–2.99(m,1H),2.97–2.89(m,2H),2.85(t,J＝4.5Hz,1H),2.61(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C32H24Br2O6Na([M+Na]+),684.9832；found,684.9806.
化合物29的理化性质如下：
1)淡黄色液体，收率75％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1733,1269,1188,839.1H NMR(400MHz,CDCl3)δ:8.29–8.18(m,6H,Ph-H),8.07(d,J＝9.6Hz,2H,Ph-H),7.34–7.28(m,3H,Ph-H),7.24–7.21(m,2H,Ph-H),6.76(d,J＝8.0Hz,1H,Ph-H),5.17–5.10(m,1H,OCH),4.58–4.54(m,1H,COOCH2),4.49–4.45(m,1H,COOCH2),3.40–3.34(m,1H),3.24–3.20(m,1H),3.05–2.88(m,3H),2.86(t,J＝4.8Hz,1H),2.61(dd,J＝4.8,2.8Hz,1H)；HRMS(ESI):calcd for C32H24N2O10Na([M+Na]+),619.1323；found,619.1313.
化合物30的理化性质如下：
1)白色固体，熔点57-59℃，收率32％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1719,1255,1165,758.1H NMR(500MHz,CDCl3)δ:7.98(d,J＝9.0Hz,
2H,Ph-H),7.87(d,J＝8.5Hz,2H,Ph-H),7.31–7.29(m,2H,Ph-H),7.27–7.26(m,1H,Ph-H),7.25–7.24(m,1H,Ph-H),7.21(d,J＝8.0Hz,1H,Ph-H),6.89–6.85(m,4H,Ph-H),6.76(d,J＝8.5Hz,1H,Ph-H),5.12–5.06(m,1H,OCH),4.48–4.45(m,1H,COOCH2),4.41–4.38(m,1H,COOCH2),3.84(d,J＝3.5Hz,6H,2Ph-OCH3),3.34–3.29(m,1H),3.22–3.19(m,1H),3.03–2.94(m,2H),2.89–2.85(m,1H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C34H30O8Na([M+Na]+),589.1833；found,589.1812.
化合物31的理化性质如下：
1)白色固体，熔点87-89℃，收率23％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1725,1268,1183,744.1H NMR(500MHz,CDCl3)δ:7.92(d,J＝8.0Hz,2H,Ph-H),7.82(d,J＝8.0Hz,2H,Ph-H),7.31(d,J＝12.0Hz,2H,Ph-H),7.27–7.26(m,1H,Ph-H),7.24(s,1H,Ph-H),7.21–7.17(m,5H,Ph-H),6.76(d,J＝8.0Hz,1H,Ph-H),5.12–5.07(m,1H,OCH),4.49–4.46(m,1H,COOCH2),4.42–4.39(m,1H,COOCH2),3.34–3.29(m,1H),3.21(s,1H),3.02–2.94(m,2H),2.90–2.82(m,2H),2.60(dd,J＝4.0,2.5Hz,1H),2.39(d,J＝4.5Hz,6H,2Ph-CH3)；HRMS(ESI):calcd for C34H30O6Na([M+Na]+),557.1935；found,557.1935.
化合物32的理化性质如下：
1)淡黄色液体，收率20％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1743,1231,1193,707.1H NMR(500MHz,CDCl3)δ:7.32–7.27(m,8H,Ph-H),7.22–7.19(m,2H,Ph-H),7.16–7.14(m,2H,Ph-H),7.10–7.07(m,2H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.73(d,J＝8.5Hz,1H,Ph-H),5.04–4.99(m,1H,OCH),4.38–4.35(m,1H,COOCH2),4.28–4.25(m,1H,COOCH2),3.68(d,J＝6.0Hz,4H,CH2Ph),3.23–3.15(m,2H),2.92–2.83(m,3H),2.82(t,J＝4.5Hz,1H),2.57(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC34H30O6Na([M+Na]+),557.1935；found,557.1937.
化合物33的理化性质如下：
1)淡黄色液体，收率47％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1744,1227,1191,725.1H NMR(500MHz,CDCl3)δ:7.24–7.20(m,4H,Ph-H),7.11–7.06(m,4H,Ph-H),7.02–6.94(m,5H,Ph-H),6.73(d,J＝8.5Hz,1H,Ph-H),5.04–4.99(m,1H,OCH),4.39–4.36(m,1H,COOCH2),4.29–4.25(m,1H,COOCH2),3.65(d,J＝6.0Hz,4H,2CH2Ph),3.23–3.15(m,2H),2.92–2.84(m,3H),2.82(t,J＝4.5Hz,1H),2.57(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C34H28F2O6Na([M+Na]+),593.1746；found,593.1747.
化合物34的理化性质如下：
1)淡黄色液体，收率34％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1743,1231,1187,748.1H NMR(500MHz,CDCl3)δ:7.28–7.27(m,1H,Ph-H),7.24–7.22(m,4H,Ph-H),7.21–7.18(m,3H,Ph-H),7.07–7.05(m,4H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.73(d,J＝8.5Hz,1H,Ph-H),5.05–5.00(m,1H,OCH),4.40–4.37(m,1H,COOCH2),4.29–4.25(m,1H,COOCH2),3.64(d,J＝5.0Hz,4H,2CH2Ph),3.22–3.15(m,2H),2.92–2.84(m,3H),2.82(t,J＝4.5Hz,1H),2.57(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcdfor C34H28Cl2O6Na([M+Na]+),625.1155；found,625.1149.
化合物35的理化性质如下：
1)淡黄色液体，收率28％；
2)该化合物的红外光谱图、核磁共振谱图特征：
IR cm-1(KBr):1739,1244,1185,759.1H NMR(500MHz,CDCl3)δ:7.16–7.15(m,4H,Ph-H),7.08–7.00(m,5H,Ph-H),6.83–6.97(m,4H,Ph-H),6.72(d,J＝8.0Hz,1H,Ph-H),5.02–4.97(m,1H,OCH),4.37–4.34(m,1H,COOCH2),4.29–4.25(m,1H,COOCH2),3.78(d,J＝8.0Hz,6H,2Ph-OCH3),3.60(s,4H,2CH2Ph),3.22–3.14(m,2H),2.92–2.82(m,3H),2.80(t,J＝4.5Hz,1H),2.56(dd,J＝5.0,2.5Hz,1H).
化合物36的理化性质如下：
1)淡黄色液体，收率56％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1731,1279,1188,739.1H NMR(500MHz,CDCl3)δ:9.24(s,1H,Ar-H),9.14(s,1H,Ar-H),8.79(dd,J＝12.5,3.5Hz,2H,Ar-H),8.27(d,J＝8.0Hz,1H,Ar-H),8.17(d,J＝7.5Hz,1H,Ar-H),7.40–7.33(m,3H,Ar-H),7.30–7.29(m,2H,Ar-H),7.23–7.21(m,2H,Ar-H),6.77(d,J＝7.5Hz,1H,Ar-H),5.15–5.10(m,1H,OCH),4.56–4.53(m,1H,COOCH2),4.48–4.45(m,1H,COOCH2),3.38–3.33(m,1H),3.24–3.20(m,1H),3.05–3.01(m,1H),2.97–2.90(m,2H),2.86(t,J＝4.5Hz,1H),2.62(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd forC30H25N2O6([M+H]+),509.1707；found,509.1717.
化合物37的理化性质如下：
1)白色固体，熔点55-57℃，收率45％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1734,1223,1187,769.1H NMR(500MHz,CDCl3)δ:8.41–8.37(m,2H,Ar-H),8.32–8.28(m,1H,Ar-H),8.24–8.21(m,1H,Ar-H),7.33–7.32(m,2H,Ar-H),7.29–7.27(m,2H,Ar-H),7.24(d,J＝1.5Hz,2H,Ar-H),7.20(d,J＝8.0Hz,1H,Ar-H),6.77(d,J＝8.5Hz,1H,Ar-H),5.15–5.10(m,1H,OCH),4.56–4.53(m,1H,COOCH2),4.50–4.47(m,1H,COOCH2),3.40–3.35(m,1H),3.23–3.19(m,1H),3.09–3.05(m,1H),2.93(d,J＝5.0Hz,2H),2.85(t,J＝5.0Hz,1H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C30H22F2N2O6Na([M+Na]+),567.1338；found,567.1340.
化合物38的理化性质如下：
1)白色固体，熔点53-55℃，收率62％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1732,1259,1187,766.1H NMR(500MHz,CDCl3)δ:8.89(s,1H,Ar-H),8.74(s,1H,Ar-H),8.39(t,J＝8.0Hz,1H,Ar-H),8.29(t,J＝8.0Hz,1H,Ar-H),7.32–7.28(m,2H,Ar-H),7.27(s,1H,Ar-H),7.22(d,J＝8.0Hz,2H,Ar-H),7.01–6.96(m,2H,Ar-H),6.76(d,J＝8.0Hz,1H,Ar-H),5.14–5.09(m,1H,OCH),4.56–4.53(m,1H,COOCH2),4.48–4.45(m,1H,COOCH2),3.39–3.34(m,1H),3.23–3.20(m,1H),3.05–3.00(m,1H),2.94(d,J＝5.5Hz,2H),2.85(t,J＝4.0Hz,1H),2.61(t,J＝4.5Hz,1H)；HRMS(ESI):calcd forC30H22F2N2O6Na([M+Na]+),567.1338；found,567.1333.
化合物39的理化性质如下：
1)白色固体，熔点60-62℃，收率9％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1733,1280,1189,756.1H NMR(500MHz,CDCl3)δ:9.00(d,J＝3.0Hz,1H,Ar-H),8.85(d,J＝2.0Hz,1H,Ar-H),8.22(dd,J＝8.0,2.5Hz,1H,Ar-H),8.11–8.08(m,1H,Ar-H),7.42–7.28(m,5H,Ar-H),7.22(d,J＝8.5Hz,2H,Ar-H),6.76(d,J＝8.5Hz,1H,Ar-H),5.15–5.10(m,1H,OCH),4.57–4.54(m,1H,COOCH2),4.49–4.45(m,1H,COOCH2),3.40–3.35(m,1H),3.24–3.20(m,1H),3.05–3.00(m,1H),2.94(d,J＝5.0Hz,2H),2.85(t,J＝4.5Hz,1H),2.61(dd,J＝5.0,3.0Hz,1H)；HRMS(ESI):calcd for C30H22Cl2N2O6Na([M+Na]+),599.0747；found,599.0733.
化合物40的理化性质如下：
1)白色固体，熔点49-51℃，收率52％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1736,1234,1186,774.1H NMR(500MHz,CDCl3)δ:8.31(dd,J＝5.0,2.0Hz,1H,Ar-H),8.28(dd,J＝4.5,2.0Hz,1H,Ar-H),8.07(dd,J＝7.5,2.0Hz,1H,Ar-H),7.99–7.97(m,1H,Ar-H),7.30–7.29(m,2H,Ar-H),7.28–7.27(m,1H,Ar-H),7.25(s,1H,Ar-H),7.21(d,J＝8.5Hz,1H,Ar-H),6.90–6.86(m,2H,Ar-H),6.79(d,J＝8.0Hz,1H,Ar-H),5.14–5.09(m,1H,OCH),4.54–4.51(m,1H,COOCH2),4.46–4.42(m,1H,COOCH2),4.03(s,3H,Ar-OCH3),3.94(s,3H,Ar-OCH3),3.36–3.31(m,1H),3.22–3.19(m,1H),3.10–3.05(m,1H),2.97–2.88(m,2H),2.84(t,J＝4.5Hz,1H),2.60(dd,J＝4.5,2.5Hz,1H)；HRMS(ESI):calcdfor C32H28N2O8Na([M+Na]+),591.1738；found,591.1732.
化合物41的理化性质如下：
1)白色固体，熔点48-50℃，收率66％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1726,1267,1190,771.1H NMR(500MHz,CDCl3)δ:8.85(d,J＝2.0Hz,1H,Ar-H),8.76(d,J＝2.5Hz,1H,Ar-H),8.12(dd,J＝8.5,2.5Hz,1H,Ar-H),8.01(dd,J＝8.5,2.5Hz,1H,Ar-H),7.31(d,J＝2.5Hz,1H,Ar-H),7.28–7.27(m,2H,Ar-H),7.24–7.22(m,1H,Ar-H),7.21(d,J＝8.5Hz,1H,Ar-H),6.76–6.70(m,3H,Ar-H),5.13–5.08(m,1H,OCH),4.52–4.49(m,1H,COOCH2),4.45–4.42(m,1H,COOCH2),3.99(d,J＝6.0Hz,6H,2Ar-OCH3),3.36–3.31(m,1H),3.23–3.19(m,1H),3.05–3.01(m,1H),2.98–2.87(m,2H),2.85(t,J＝5.0Hz,1H),2.61(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C32H28N2O8Na([M+Na]+),591.1738；found,591.1728.
化合物42的理化性质如下：
1)黄色固体，熔点64-66℃，收率66％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1715,1270,1191,821.1H NMR(500MHz,CDCl3)δ:7.35(s,1H,Ph-H),7.33(d,J＝8.5Hz,1H,Ph-H),7.27(s,1H,Ph-H),7.25–7.24(m,1H,Ph-H),7.20(d,J＝8.0Hz,1H,Ph-H),6.89(d,J＝8.0Hz,1H,Ph-H),5.13–5.08(m,1H,OCH),4.82(s,2H,Ferrocene-H),4.76(d,J＝29.5Hz,2H,Ferrocene-H),4.46–4.42(m,3H,Ferrocene-H,COOCH2),4.37–4.33(m,3H,Ferrocene-H,COOCH2),4.17(s,5H,Ferrocene-H),4.07(s,5H,Ferrocene-H),3.42–3.37(m,1H),3.22–3.18(m,1H),3.13–3.09(m,1H),2.97–2.93(m,1H),2.89–2.82(m,2H),2.60(dd,J＝5.0,2.5Hz,1H)；HRMS(ESI):calcd for C40H34Fe2O6Na([M+Na]+),745.0948；found,745.0940.
化合物43的理化性质如下：
1)淡黄色液体，收率92％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1747,1225,1190,830.1H NMR(400MHz,CDCl3)δ:7.26(d,J＝2.8Hz,1H,Ph-H),7.23–7.18(m,3H,Ph-H),7.06(d,J＝8.0Hz,1H,Ph-H),6.84(d,J＝8.4Hz,1H,Ph-H),5.08–5.01(m,1H,OCH),4.38–4.34(m 1H,COOCH2),4.26–4.21(m,1H,COOCH2),3.38–3.31(m,1H),3.20–3.15(m,1H),3.03–2.98(m,1H),2.94–2.80(m,3H),2.59(dd,J＝4.8,2.8Hz,1H),2.12(d,J＝4.4Hz,6H,2COOCH3)；HRMS(ESI):calcd for C22H22O6Na([M+Na]+),405.1309；found,405.1317.
化合物44的理化性质如下：
1)淡黄色液体，收率85％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1745,1241,1183,830.1H NMR(400MHz,CDCl3)δ:7.24–7.15(m,4H,Ph-H),7.04(d,J＝8.4Hz,1H,Ph-H),6.82(d,J＝8.0Hz,1H,Ph-H),5.07–5.00(m,1H,OCH),4.38–4.34(m,1H,COOCH2),4.26–4.21(m,1H,COOCH2),3.36–3.30(m,1H),3.20–3.15(m,1H),3.03–2.97(m,1H),2.94–2.80(m,3H),2.58(dd,J＝4.8,2.4Hz,1H),2.36(t,J＝7.6Hz,4H,2OCOCH2),1.70–1.55(m,4H,2CH2),0.96(t,J＝7.2Hz,3H,CH3),0.88(t,J＝7.2Hz,3H,CH3)；HRMS(ESI):calcd for C26H30O6Na([M+Na]+),461.1935；found,461.1941.
化合物45的理化性质如下：
1)淡黄色液体，收率97％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1749,1232,1159,830.1H NMR(400MHz,CDCl3)δ:7.24–7.16(m,4H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.82(d,J＝8.0Hz,1H,Ph-H),5.07–4.99(m,1H,OCH),4.38–4.34(m,1H,COOCH2),4.26–4.21(m,1H,COOCH2),3.36–3.30(m,1H),3.18–3.15(m,1H),3.03–2.80(m,4H),2.58–2.56(m,1H),2.38(t,J＝7.2Hz,4H,2OCOCH2),1.64–1.54(m,4H,2CH2),1.32–1.18(m,8H,4CH2),0.90–0.85(m,6H,2CH3)；HRMS(ESI):calcd for C30H38O6Na([M+Na]+),517.2561；found,517.2557.
化合物46的理化性质如下：
1)淡黄色液体，收率93％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1747,1230,1190,830.1H NMR(400MHz,CDCl3)δ:7.24–7.20(m,3H,Ph-H),7.18–7.15(m,1H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.82(d,J＝8.0Hz,1H,Ph-H),5.06–4.99(m,1H,OCH),4.38–4.34(m,1H,COOCH2),4.26–4.21(m,1H,COOCH2),3.36–3.30(m,1H),3.20–3.15(m,1H),3.02–2.97(m,1H),2.94–2.89(m,1H),2.87–2.80(m,2H),2.58(dd,J＝5.2,2.8Hz,1H),2.38–2.34(m,4H,2OCOCH2),1.64–1.53(m,4H,2CH2),1.29–1.24(m,16H,8CH2),0.89–0.86(m,6H,2CH3)；HRMS(ESI):calcd for C34H46O6Na([M+Na]+),573.3187；found,573.3185.
化合物47的理化性质如下：
1)淡黄色液体，收率96％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1747,1236,1154,837.1H NMR(400MHz,CDCl3)δ:7.24–7.20(m,3H,Ph-H),7.18–7.15(dd,J＝8.4,2.0Hz,1H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.82(d,J＝8.0Hz,1H,Ph-H),5.06–4.99(m,1H,OCH),4.38–4.34(m,1H,COOCH2),4.25–4.21(m,1H,COOCH2),3.36–3.30(m,1H),3.20–3.15(m,1H),3.02–2.97(m,1H),2.94–2.89(m,1H),2.87–2.80(m,2H),2.58–2.56(m,1H),2.37–2.33(m,4H,2OCOCH2),1.65–1.53(m,4H,2CH2),1.28–1.24(m,32H,16CH2),0.89–0.86(m,6H,2CH3)；HRMS(ESI):calcd for C42H62O6Na([M+Na]+),685.4439；found,685.4436.
化合物48的理化性质如下：
1)淡黄色液体，收率96％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1747,1236,1197,837.1H NMR(400MHz,CDCl3)δ:7.24–7.23(d,J＝2.0Hz,1H,Ph-H),7.22–7.20(m,2H,Ph-H),7.18(dd,J＝8.4,1.6Hz,1H,Ph-H),7.04(d,J＝8.0Hz,1H,Ph-H),6.82(d,J＝8.4Hz,1H,Ph-H),5.06–4.99(m,1H,OCH),4.38–4.34(m,1H,COOCH2),4.25–4.21(m,1H,COOCH2),3.36–3.29(m,1H),3.20–3.15(m,1H),3.02–2.97(m,1H),2.94–2.89(m,1H),2.87–2.80(m,2H),2.58(dd,J＝4.8,2.4Hz,1H),2.37–2.33(m,4H,2OCOCH2),1.65–1.55(m,4H,2CH2),1.31–1.25(m,40H,20CH2),0.89(t,J＝6.4Hz,6H,2CH3)；HRMS(ESI):calcd for C46H70O6Na([M+Na]+),741.5065；found,741.5046.
化合物49的理化性质如下：
1)白色固体，熔点42-44℃，收率67％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1747,1231,1200,837.1H NMR(500MHz,CDCl3)δ:7.23–7.15(m,4H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.5Hz,1H,Ph-H),5.05–4.99(m,1H,OCH),4.36–4.34(m,1H,OCH2),4.25–4.22(m,1H,OCH2),3.35–3.30(m,1H),3.17(s,1H),3.02–2.97(m,1H),2.94–2.81(m,3H),2.58–2.57(m,1H),2.36(t,J＝7.5Hz,4H,2OCOCH2),1.63–1.54(m,4H,2CH2),1.31–1.25(m,48H,24CH2),0.89(t,J＝6.0Hz,6H,2CH3)；HRMS(ESI):calcd for C50H78O6Na([M+Na]+),797.5691；found,797.5677.
化合物50的理化性质如下：
1)白色固体，熔点49-51℃，收率50％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1744,1225,1189,834.1H NMR(500MHz,CDCl3)δ:7.23–7.20(m,3H,Ph-H),7.17(d,J＝8.5Hz,1H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.5Hz,1H,Ph-H),5.05–4.99(m,1H,OCH),4.37–4.34(m,1H,OCH2),4.25–4.21(m,1H,OCH2),3.35–3.30(m,1H),3.17(s,1H),3.02–2.97(m,1H),2.93–2.89(m,1H),2.86–2.81(m,2H),2.57–2.56(m,1H),2.36(t,J＝7.5Hz,4H,2OCOCH2),1.63–1.55(m,4H,2CH2),1.31–1.25(m,56H,28CH2),0.89(t,J＝6.5Hz,6H,2CH3)；HRMS(ESI):calcd for C54H86O6Na([M+Na]+),853.6317；found,853.6300.
化合物51的理化性质如下：
1)淡黄色液体，收率48％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：
IR cm-1(KBr):1747,1231,1187,829.1H NMR(500MHz,CDCl3)δ:7.23–7.15(m,4H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.0Hz,1H,Ph-H),5.05–4.99(m,1H,OCH),4.37–4.34(m,1H,OCH2),4.25–4.22(m,1H,OCH2),3.35–3.30(m,1H),3.19–3.15(m,1H),3.02–2.97(m,1H),2.93–2.89(m,1H),2.86–2.80(m,2H),2.58(dd,J＝5.0,2.5Hz,1H),2.37(t,J＝7.5Hz,4H,2OCOCH2),1.63–1.54(m,4H,2CH2),1.32–1.25(s,36H,18CH2),0.89(t,J＝6.0Hz,6H,2CH3)；HRMS(ESI):calcd for C44H66O6Na([M+Na]+),713.4752；found,713.4737.
化合物52的理化性质如下：
1)淡黄色液体，收率53％；
2)该化合物的红外光谱图、核磁共振谱图、高分辨质谱特征：IR cm-1(KBr):1745,1233,1195,838.1H NMR(500MHz,CDCl3)δ:7.23–7.15(m,4H,Ph-H),7.03(d,J＝8.0Hz,1H,Ph-H),6.81(d,J＝8.0Hz,1H,Ph-H),5.02–4.99(m,1H,OCH),4.37–4.34(m,1H,OCH2),4.25–4.21(m,1H,OCH2),3.35–3.30(m,1H),3.19–3.15(m,1H),3.02–2.97(m,1H),2.93–2.80(m,3H),2.58(dd,J＝5.0,2.5Hz,1H),2.37(t,J＝7.5Hz,4H,2OCOCH2),1.63–1.55(m,4H,2CH2),1.32–1.24(s,44H,22CH2),0.89(t,J＝6.0Hz,6H,2CH3)；HRMS(ESI):calcd for C48H74O6Na([M+Na]+),769.5378；found,769.5361.
实施例4：朱砂叶螨生测实验：
1、供试昆虫：朱砂叶螨(TetranychuscinnabarinusBois.)，由本实验室传代饲养。
2、样品及试剂：样品为：98.32％螺螨酯原药(陕西美邦农药有限公司提供)(阳性对照)，和厚朴酚，中间体b及实施例1制备的化合物1-52，丙酮(溶剂，成都市科龙化工试剂厂，分析纯)、水。
3、生测方法：采用FAO推荐的玻片浸渍法：
①0.1‰吐温80母液配制：称取25mg吐温80溶于5mL丙酮溶液中，用蒸馏水定溶至250mL待用。
②初筛药液配制：分别称取3.0mg供试化合物，用120微升丙酮(目标体积的2％)溶解，再用配好的0.1‰吐温80定容至6.0mL，即配置成500mg/L药液，供初筛使用。
③供试螨的准备：将1cm宽的双面胶的贴在载玻片的一端，用0号毛笔挑选健康活泼、螨龄一致的朱砂叶螨雌成螨，小心整齐地将其背部粘在双面胶上，每块玻片粘约35头，排成2行，将粘有供试螨的玻片放在垫有湿润海绵的铁盘中，并将铁盘置于26±1℃、相对湿度60％～80％、光照L∶D＝14h∶10h条件下的光照培养箱中，放置4小时后，用体视显微镜检查，剔除死亡和不活泼的个体，记录每块玻片上的活螨数量。
④浸药：将载玻片粘有螨的一端在供试药液中振荡浸渍5s后取出，用小滤纸条小心吸去多余药液(注意不能触碰到螨体)后放回铁盘，置于相同饲养条件下光照培养箱中，一块玻片为一个处理，每处理重复3次，以0.1‰吐温80溶液为空白对照。
⑤结果统计：浸药处理24小时后将玻片取出在体视显微镜下检查结果，检查时用毛笔尖轻触螨体，以其螯肢不动者为死亡，记录死亡个体数；连续观察记录72小时，结果见表1。
表1.本发明和厚朴酚、中间体b及其衍生物1～52的杀螨活性
结果表明，上述部分和厚朴酚并二氢呋喃酯类衍生物72h杀螨活性较和厚朴酚有显著性提高，且部分衍生物72h杀螨活性与螺螨酯相当，故有望用于制备高效、环保、低毒的植物源杀螨剂。
实施例5：苹果黄蚜生测实验
1、供试昆虫：苹果黄蚜(Aphis citricola van der Goot)(采自西北农林科技大学试验农场)；
2、样品及试剂：样品为：和厚朴酚，中间体b及实施例1制备的化合物1-52，丙酮(溶剂，成都市科龙化工试剂厂，分析纯)、水。
3、生测方法
采用FAO推荐的微量点滴法：
①用丙酮将供试化合物及对照药剂配制成浓度为1mg/mL的溶液备用(灭多威浓度为100mg/L)，以丙酮作为空白对照，灭多威为阳性对照。
②将挑好的蚜虫(大小一致、健康的无翅成蚜)在虫体前胸背板处点滴约0.04μL供试药液，然后将试虫转入直径为9cm的底部垫有滤纸保湿的培养皿中，每皿30头，每个培养皿为一个重复，每个处理重复3次，饲喂新鲜叶片，用湿脱脂棉缠住叶柄处，然后用纱布(或卫生纸)覆盖，置于光周期L:D＝14h:10h、温度(25±1)℃、相对湿度(50±7)％条件下饲养。
③分别于24h、48h后观察并记录试虫的死亡情况，蚜虫的死亡判断以毛笔触足和触角时完全不动为死亡，结果见表2。
表2 本发明和厚朴酚、中间体b及其衍生物1～52的杀蚜虫活性
结果表明，部分和厚朴酚并二氢呋喃酯类衍生物对苹果黄蚜的最终死亡率高于其母体和厚朴酚。说明本发明的化合物对苹果黄蚜具有较好杀虫活性，故有望用于制备环保、低毒的植物源杀虫剂。
最后说明的是，以上实施例仅用以说明本发明的技术方案而非限制，本领域普通技术人员对本发明的技术方案所做的其他修改或者等同替换，只要不脱离本发明技术方案的精神和原理，均应涵盖在本发明的权利要求范围当中。
Claims (6)
1.一种和厚朴酚并二氢呋喃酯类衍生物，其特征在于，所述和厚朴酚并二氢呋喃酯类衍生物的化学结构式如式（I）所示：
其中，所述的和厚朴酚并二氢呋喃酯类衍生物具有以下结构之一：
（1）R1=COPh；R2=H
（2）R1=CO(4-F)-Ph；R2=H
（3）R1=CO(4-Cl)-Ph；R2=H
（4）R1=CO(4-Br)-Ph；R2=H
（7）R1=CO(4-CH3)-Ph；R2=H
（9）R1=COCH2-(4-F)-Ph；R2=H
（10）R1=COCH2-(4-Cl)-Ph；R2=H
（13）R1=COFerrocene；R2=H
（15）R1=CO(CH2)2CH3；R2=H
（16）R1=CO(CH2)4CH3；R2=H
（17）R1=CO(CH2)6CH3；R2=H
（19）R1=CO(CH2)12CH3；R2=H
（20）R1=CO(CH2)14CH3；R2=H
（21）R1=CO(CH2)16CH3；R2=H
（22）R1=CO(CH2)11CH3；R2=H
（23）R1=CO(CH2)13CH3；R2=H
（24）R1=COPh；R2=COPh
（25）R1=CO(4-F)-Ph；R2=CO(4-F)-Ph
（27）R1=CO(3-Cl)-Ph；R2=CO(3-Cl)-Ph
（28）R1=CO(4-Br)-Ph；R2=CO(4-Br)-Ph
（29）R1=CO(4-NO2)-Ph；R2=CO(4-NO2)-Ph
（30）R1=CO(4-OCH3)-Ph；R2=CO(4-OCH3)-Ph
（31）R1=CO(4-CH3)-Ph；R2=CO(4-CH3)-Ph
（33）R1=COCH2-(4-F)-Ph；R2=COCH2-(4-F)-Ph
（36）R1=COPy；R2=COPy
（38）R1=CO(6-F)-Py；R2=CO(6-F)-Py
（39）R1=CO(6-Cl)-Py；R2=CO(6-Cl)-Py
（40）R1=CO(2-OCH3)-Py；R2=CO(2-OCH3)-Py
（43）R1=COCH3；R2=COCH3
（44）R1=CO(CH2)2CH3；R2=CO(CH2)2CH3
（45）R1=CO(CH2)4CH3；R2=CO(CH2)4CH3
（46）R1=CO(CH2)6CH3；R2=CO(CH2)6CH3
（47）R1=CO(CH2)10CH3；R2=CO(CH2)10CH3
（48）R1=CO(CH2)12CH3；R2=CO(CH2)12CH3
（49）R1=CO(CH2)14CH3；R2=CO(CH2)14CH3
（50）R1=CO(CH2)16CH3；R2=CO(CH2)16CH3
（51）R1=CO(CH2)11CH3；R2=CO(CH2)11CH3
（52）R1=CO(CH2)13CH3；R2=CO(CH2)13CH3。
2.如权利要求1所述的和厚朴酚并二氢呋喃酯类衍生物的制备方法，其特征在于，包括如下步骤：
步骤1：向和厚朴酚中加入间氯过氧苯甲酸和碳酸钾反应制得中间体b；
步骤2：将步骤1制得的中间体b与取代羧酸反应，得到式（I）所示化合物；
所述步骤2中取代羧酸选自PhCOOH、(4-F)-PhCOOH、(3-Cl)-PhCOOH、(4-Cl)-PhCOOH、(4-Br)-PhCOOH、(4-NO2)-PhCOOH、(4-OCH3)-PhCOOH、(4-CH3)-PhCOOH、(4-F)-Ph-CH2COOH、(4-Cl)-Ph-CH2COOH、烟酸、6-氟烟酸、6-氯烟酸、2-甲氧烟酸、二茂铁甲酸、CH3COOH、CH3(CH2)2COOH、CH3(CH2)4COOH、CH3(CH2)6COOH、CH3(CH2)10COOH、CH3(CH2)12COOH、CH3(CH2)14COOH、CH3(CH2)16COOH、CH3(CH2)11COOH、CH3(CH2)13COOH中的一种。
3.如权利要求2所述的和厚朴酚并二氢呋喃酯类衍生物的制备方法，其特征在于，步骤1包括将和厚朴酚和间氯过氧苯甲酸在二氯甲烷中进行反应后除去二氯甲烷，然后加入碳酸钾并在甲醇中反应，反应温度为20~30℃。
4.如权利要求2所述的和厚朴酚并二氢呋喃酯类衍生物的制备方法，其特征在于，步骤2包括将中间体b与取代羧酸在无水二氯甲烷中反应，同时加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和4-二甲氨基吡啶，反应温度为20~30℃。
5.一种和厚朴酚并二氢呋喃酯类衍生物用于制备杀虫剂的应用，所述虫为苹果黄蚜，所述和厚朴酚并二氢呋喃酯类衍生物的化学结构式如式（I）所示：
其中，所述的和厚朴酚并二氢呋喃酯类衍生物具有以下结构之一：
（1）R1=COPh；R2=H
（2）R1=CO(4-F)-Ph；R2=H
（3）R1=CO(4-Cl)-Ph；R2=H
（4）R1=CO(4-Br)-Ph；R2=H
（7）R1=CO(4-CH3)-Ph；R2=H
（9）R1=COCH2-(4-F)-Ph；R2=H
（10）R1=COCH2-(4-Cl)-Ph；R2=H
（15）R1=CO(CH2)2CH3；R2=H
（16）R1=CO(CH2)4CH3；R2=H
（17）R1=CO(CH2)6CH3；R2=H
（19）R1=CO(CH2)12CH3；R2=H
（21）R1=CO(CH2)16CH3；R2=H
（24）R1=COPh；R2=COPh
（25）R1=CO(4-F)-Ph；R2=CO(4-F)-Ph
（28）R1=CO(4-Br)-Ph；R2=CO(4-Br)-Ph
（29）R1=CO(4-NO2)-Ph；R2=CO(4-NO2)-Ph
（31）R1=CO(4-CH3)-Ph；R2=CO(4-CH3)-Ph
（33）R1=COCH2-(4-F)-Ph；R2=COCH2-(4-F)-Ph
（36）R1=COPy；R2=COPy
（38）R1=CO(6-F)-Py；R2=CO(6-F)-Py
（39）R1=CO(6-Cl)-Py；R2=CO(6-Cl)-Py
（40）R1=CO(2-OCH3)-Py；R2=CO(2-OCH3)-Py
（43）R1=COCH3；R2=COCH3
（45）R1=CO(CH2)4CH3；R2=CO(CH2)4CH3
（46）R1=CO(CH2)6CH3；R2=CO(CH2)6CH3
（47）R1=CO(CH2)10CH3；R2=CO(CH2)10CH3
（48）R1=CO(CH2)12CH3；R2=CO(CH2)12CH3
（49）R1=CO(CH2)14CH3；R2=CO(CH2)14CH3。
6.一种和厚朴酚并二氢呋喃酯类衍生物用于制备杀螨剂的应用，所述和厚朴酚并二氢呋喃酯类衍生物的化学结构式如式（I）所示：
其中，所述的和厚朴酚并二氢呋喃酯类衍生物具有以下结构之一：
（13）R1=COFerrocene；R2=H
（19）R1=CO(CH2)12CH3；R2=H
（20）R1=CO(CH2)14CH3；R2=H
（21）R1=CO(CH2)16CH3；R2=H
（22）R1=CO(CH2)11CH3；R2=H
（23）R1=CO(CH2)13CH3；R2=H
（27）R1=CO(3-Cl)-Ph；R2=CO(3-Cl)-Ph
（28）R1=CO(4-Br)-Ph；R2=CO(4-Br)-Ph
（29）R1=CO(4-NO2)-Ph；R2=CO(4-NO2)-Ph
（30）R1=CO(4-OCH3)-Ph；R2=CO(4-OCH3)-Ph
（31）R1=CO(4-CH3)-Ph；R2=CO(4-CH3)-Ph
（43）R1=COCH3；R2=COCH3
（44）R1=CO(CH2)2CH3；R2=CO(CH2)2CH3
（45）R1=CO(CH2)4CH3；R2=CO(CH2)4CH3
（46）R1=CO(CH2)6CH3；R2=CO(CH2)6CH3
（47）R1=CO(CH2)10CH3；R2=CO(CH2)10CH3
（48）R1=CO(CH2)12CH3；R2=CO(CH2)12CH3
（49）R1=CO(CH2)14CH3；R2=CO(CH2)14CH3
（50）R1=CO(CH2)16CH3；R2=CO(CH2)16CH3
（51）R1=CO(CH2)11CH3；R2=CO(CH2)11CH3
（52）R1=CO(CH2)13CH3；R2=CO(CH2)13CH3。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1780825A (zh) * | 2003-04-30 | 2006-05-31 | Fmc有限公司 | 杀虫剂(二卤代丙烯基)苯基烷基取代的二氢苯并呋喃和二氢苯并吡喃衍生物 |
| CN103724223A (zh) * | 2013-12-23 | 2014-04-16 | 西北农林科技大学 | 偶氮厚朴酚/和厚朴酚及硝化厚朴酚类衍生物及制备植物源杀虫剂的应用 |
| CN108864007A (zh) * | 2018-09-10 | 2018-11-23 | 湖南大学 | 2-氨甲基-6-(苯并呋喃-5-基)苯酚及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586627B2 (en) * | 2007-05-03 | 2013-11-19 | Jack L. Arbiser | Honokiol analogs and their use in treating cancers |
| PT2995604T (pt) * | 2013-05-09 | 2019-10-11 | Sichuan Haisco Pharmaceutical Co Ltd | Derivado de fenol e seu processo de preparação e utilização em medicina |
| CN104870429B (zh) * | 2013-05-22 | 2017-05-03 | 四川海思科制药有限公司 | 苯并呋喃衍生物、其制备方法及其在医药上的应用 |
| US10730872B2 (en) * | 2015-11-16 | 2020-08-04 | Syngenta Participations Ag | Pesticidally active heterocyclic derivatives with sulphur containing sustitutents |
| US20160376263A1 (en) * | 2016-07-26 | 2016-12-29 | Senomyx, Inc. | Bitter taste modifiers including substituted 1-benzyl-3-(1-(isoxazol-4-ylmethyl)-1h-pyrazol-4-yl)imidazolidine-2,4-diones and compositions thereof |
| CN111533715B (zh) * | 2020-04-22 | 2021-04-06 | 南京农业大学 | 2(5h)-呋喃-2-酮衍生物及其制备方法以及在抑制水稻分蘖的应用 |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1780825A (zh) * | 2003-04-30 | 2006-05-31 | Fmc有限公司 | 杀虫剂(二卤代丙烯基)苯基烷基取代的二氢苯并呋喃和二氢苯并吡喃衍生物 |
| CN103724223A (zh) * | 2013-12-23 | 2014-04-16 | 西北农林科技大学 | 偶氮厚朴酚/和厚朴酚及硝化厚朴酚类衍生物及制备植物源杀虫剂的应用 |
| CN108864007A (zh) * | 2018-09-10 | 2018-11-23 | 湖南大学 | 2-氨甲基-6-(苯并呋喃-5-基)苯酚及其制备方法与应用 |
Non-Patent Citations (2)
| Title |
|---|
| Natural products-based insecticidal agents 20. Design, synthesis and insecticidal activity of novel honokiol/magnolol azo derivatives;Chun Yang，et al.;《Industrial Crops and Products》;20150814;第76卷;第761-767页 * |
| 代表性木脂素类化合物的结构修饰研究概况;金鑫 等;《中草药》;20181231;第49卷(第23期);第5724-5732页 * |
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