CN111233692A - 一种香茅酸酰胺类衍生物及其制备方法与应用 - Google Patents
一种香茅酸酰胺类衍生物及其制备方法与应用 Download PDFInfo
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- CN111233692A CN111233692A CN202010063047.8A CN202010063047A CN111233692A CN 111233692 A CN111233692 A CN 111233692A CN 202010063047 A CN202010063047 A CN 202010063047A CN 111233692 A CN111233692 A CN 111233692A
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Classifications
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- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
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- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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Abstract
本发明公开了一种香茅酸酰胺类衍生物及其制备方法与应用，制备方法为：将香茅酸溶于有机溶剂中，冰浴滴加由有机溶剂溶解的酰氯化试剂，滴加完毕后，升温至30～60℃，反应结束后减压蒸馏除溶剂，得香茅酰氯；将香茅酸酰氯溶于有机溶剂中，冰水浴条件下搅拌，搅拌后缓慢滴加到盛有芳胺、三乙胺和有机溶剂的容器中，滴加完毕后，升温至50～80℃进行反应，反应结束后，减压蒸馏除溶剂，柱层析得香茅酸酰胺类衍生物纯品。该衍生物作为抗菌剂对植物病原真菌表现出良好的抗菌活性，在制备抗菌剂中将具有广泛的应用。
Description
技术领域
本发明属于有机化合物技术领域，具体涉及一种香茅酸酰胺类衍生物及其制备方法与应用。
背景技术
目前已经知道多种酰胺类抗菌剂类型，包括磺酰胺类、单环β-内酰胺类、林可酰胺类、苯基酰胺类，但已长期使用商品抗菌剂使得植物病原菌产生一定的耐受性，且对环境造成很大影响。因此，持续需要安全、绿色、高效的新型抗菌剂，去克服现有抗菌剂所遇到的问题。
在植物病原菌中，已经产生许多种耐药菌株。如稻瘟病对春雷霉素和稻瘟散的抗性，我国南方双季稻稻瘟病对异稻瘟净的抗药亚群体形成并逐渐扩大，如广西平南地区抗药菌株出现频率达91.67％，另外，稻瘟病菌对停用10年左右的异稻瘟净的抗药性频率仍高达79.1％。苯来特对甜菜、花生、芹菜叶斑病也产生了抗药性，抗性菌株可耐浓度比敏感菌株高出10倍。多菌灵对蔬菜灰霉病也产生很高的抗药性，且抗性频率普遍很高。一些严重的地区，多菌灵对菌核病已失去活性。水稻恶苗病对多菌灵的抗药性在部分水稻产区抗性菌株出现频率高达55％～95％。甲基硫菌灵对芦笋茎枯病的抗性频率高达50％～88.9％，另外甲基硫菌灵对小麦赤霉病、梨黑星病、柑橘绿霉病及柑橘青霉病都产生了不同程度的抗药性。致病疫霉对甲霜灵的抗药性高达12495倍，黄瓜霜霉病对甲霜灵的抗药性高达2404倍。优于卵菌对甲霜灵严重抗性的出现，使得高效杀毒矾(恶霜灵+代森锰锌)防治失效。白粉病对三唑酮的抗性也很强，每公顷施药量由原来75～100g(有效成分)增加到450g，持效期由42～56d降至5～7d。三唑酮对于防治沿海地区葫芦科作物和新疆地区哈密瓜几乎无效。
发明内容
本发明提出了一种香茅酸酰胺类衍生物及其制备方法与应用，以解决上述背景技术中提出的问题。本发明的技术方案是这样实现的：
一种香茅酸酰胺类衍生物，化学结构通式为：
在本发明的香茅酸酰胺类衍生物中，R1表示任选被取代的C6芳基时，化学式为：
一种香茅酸酰胺类衍生物的制备方法，步骤如下：
步骤一：将香茅酸溶于有机溶剂中，冰浴滴加由有机溶剂溶解的酰氯化试剂，滴加完毕后，升温至30～60℃，反应结束后减压蒸馏除溶剂，得香茅酰氯；
步骤二：将香茅酸酰氯溶于有机溶剂中，冰水浴条件下搅拌，搅拌后缓慢滴加到盛有芳胺、三乙胺和有机溶剂的容器中，滴加完毕后，升温至50～80℃进行反应，反应结束后，减压蒸馏除溶剂，柱层析得香茅酸酰胺类衍生物纯品，反应式如下：
式中，R1表示任选被取代的C6芳基、杂芳基或杂环基。
在本发明的香茅酸酰胺类衍生物的制备方法中，步骤一中，香茅酸与酰氯化试剂的摩尔比为1:1.5～1:2。
在本发明的香茅酸酰胺类衍生物的制备方法中，步骤一中，酰氯化试剂为草酰氯和二甲亚砜中任意一种。
在本发明的香茅酸酰胺类衍生物的制备方法中，步骤一中，以GC跟踪反应，显示至少一种原料消失，为反应结束。
在本发明的香茅酸酰胺类衍生物的制备方法中，步骤二中，香茅酰氯与芳胺的摩尔比为1:1.5～1:2。
在本发明的香茅酸酰胺类衍生物的制备方法中，步骤一和步骤二中，所述溶剂为二氯甲烷、三氯甲烷、四氯化碳或乙腈中任意一种。
在本发明的香茅酸酰胺类衍生物的制备方法中，以TLC跟踪反应，显示至少一种原料消失，为反应结束。
一种香茅酸酰胺类衍生物的应用，所述香茅酸酰胺类衍生物用作抗菌剂，所述抗菌剂适用于各种植物病原真菌，例如，子囊菌亚门，包括油菜菌核病菌(Sclerotiniasclerotirum)、莴苣菌核病病原菌(Lettuce sclerotinia)、辣椒菌核病病原菌(Sclerotinia sclerotiorum(Libert)de Bery)、小麦白粉病菌(Erysiphegraminis)、黄瓜白粉病菌(Sphaerothecafuligenea)、小麦赤霉病菌(Gibberella zea)、苹果轮纹病菌(Botryosphaeria berengeriana)、小麦全蚀病菌(Gaeumanomyces graminis var)、层出镰刀菌(Fusariumproliferatum)、毛竹枯梢病病原菌(Ceratosphaeriaphyllostachydissp.nov.)等；担子菌亚门，包括水稻纹枯病菌(Rhizoctonia solani)、小麦纹枯病菌(Rhizoctonia solani)等；鞭毛菌亚门，包括烟草黑胫病菌(Phytophthora parasitica)、辣椒疫霉病菌(Phytophthora capsici)、黄瓜霜霉病菌(Pseudoperonospora cubensis)、马铃薯晚疫病菌(Phytophthora infestans)等；半知菌亚门，包括油茶炭疽病菌(Colletotrichum gloeosporioides)、黄瓜炭疽病菌(Colletotrichum lagenarium)、辣椒炭疽病菌(Colletotrichum capsici)、枇杷炭疽病病原菌(Colletotrichum acutatum)、蕃茄早疫病菌(Alternaria solani)、玉米小斑病菌(Helminthosporum maydis)、柑桔青霉病菌(Penicillium italicum)柑桔蒂腐病菌(Diaporthemedusae)、烟草赤星病菌(Alternaria alternata)、棉花枯萎病菌(Fusarium)、香蕉叶斑病菌(Helminthosporiumtorulosum)、小麦根腐病菌(Bipolaris sorokiniana)、水稻稻瘟病菌(Pyriculariaoryzae)、花生褐斑病菌(Cercospora arachidicola)、稻曲病菌(Ustilaginoideavirens)、黄瓜灰霉病菌(Botrytis cinerea oxysporum)、棉花红腐病菌(Fusariummoniliforme)、梨链格孢菌(Alternaria kikuchiana)、猕猴桃果实拟茎点霉(Phomopsissp.)、七叶树壳梭孢菌(Fusicoccum aesculi)等。
本发明这种香茅酸酰胺类衍生物及其制备方法与应用，具有以下优点：
本发明的香茅酸酰胺类衍生物，制备方法简单，步骤少，损耗小，低成本，对植物病原真菌具有良好抗菌活性,例如：采用菌丝生长速率法显示，大部分衍生物对于油茶炭疽病菌(Colletotrichum gloeosporioides)的半抑制浓度IC50值与市售农药百菌清相当，其中一部分化合物的抑菌作用显著优于百菌清，分别是化合物6、7、8、11、16、17、20、26、29,在这些化合物中，化合物6对油茶炭疽病菌(Colletotrichum gloeosporioides)的抑制效果最好，其半抑制浓度IC50值为21.177mg/L,此类化合物在制备抗菌剂中将具有广泛的应用。
具体实施方式
下面结合具体实施例对本发明作进一步说明，但不作为对本发明保护范围的限定。
一种香茅酸酰胺类衍生物，化学结构通式为：
该香茅酸酰胺类衍生物的制备方法为：将香茅酸溶于有机溶剂中，冰浴滴加由有机溶剂溶解的酰氯化试剂，滴加完毕后，升温至30～60℃，以GC跟踪反应，显示至少一种原料消失，为反应结束，反应结束后减压蒸馏除溶剂，得香茅酰氯；再将香茅酸酰氯溶于有机溶剂中，冰水浴条件下搅拌，搅拌后缓慢滴加到盛有芳胺、三乙胺和有机溶剂的容器中，滴加完毕后，升温至50～80℃进行反应，以TLC跟踪反应，显示至少一种原料消失，为反应结束，反应结束后，减压蒸馏除溶剂，柱层析得香茅酸酰胺类衍生物纯品，其中，香茅酸与酰氯化试剂的摩尔比为1:1.5～1:2，香茅酰氯与芳胺的摩尔比为1:1.5～1:2，酰氯化试剂为草酰氯和二甲亚砜中任意一种，溶剂为二氯甲烷、三氯甲烷、四氯化碳或乙腈中任意一种。
反应式如下：
式中，R1表示任选被取代的C6芳基、杂芳基及杂环基。
该香茅酸酰胺类衍生物用作抗菌剂，抗菌剂可以适用于各种植物病原真菌，例如，子囊菌亚门，包括油菜菌核病菌(Sclerotinia sclerotirum)、莴苣菌核病病原菌(Lettucesclerotinia)、辣椒菌核病病原菌(Sclerotinia sclerotiorum(Libert)de Bery)、小麦白粉病菌(Erysiphe graminis)、黄瓜白粉病菌(Sphaerothecafuligenea)、小麦赤霉病菌(Gibberella zea)、苹果轮纹病菌(Botryosphaeria berengeriana)、小麦全蚀病菌(Gaeumanomyces graminis var)、层出镰刀菌(Fusariumproliferatum)、毛竹枯梢病病原菌(Ceratosphaeriaphyllostachydis sp.nov.)等；担子菌亚门，包括水稻纹枯病菌(Rhizoctonia solani)、小麦纹枯病菌(Rhizoctonia solani)等；鞭毛菌亚门，包括烟草黑胫病菌(Phytophthoraparasitica)、辣椒疫霉病菌(Phytophthora capsici)、黄瓜霜霉病菌(Pseudoperonospora cubensis)、马铃薯晚疫病菌(Phytophthora infestans)等；半知菌亚门，包括油茶炭疽病菌(Colletotrichum gloeosporioides)、黄瓜炭疽病菌(Colletotrichum lagenarium)、辣椒炭疽病菌(Colletotrichum capsici)、枇杷炭疽病病原菌(Colletotrichum acutatum)、蕃茄早疫病菌(Alternaria solani)、玉米小斑病菌(Helminthosporum maydis)、柑桔青霉病菌(Penicillium italicum)柑桔蒂腐病菌(Diaporthe medusae)、烟草赤星病菌(Alternaria alternata)、棉花枯萎病菌(Fusarium)、香蕉叶斑病菌(Helminthosporium torulosum)、小麦根腐病菌(Bipolarissorokiniana)、水稻稻瘟病菌(Pyricularia oryzae)、花生褐斑病菌(Cercosporaarachidicola)、稻曲病菌(Ustilaginoidea virens)、黄瓜灰霉病菌(Botrytis cinereaoxysporum)、棉花红腐病菌(Fusarium moniliforme)、梨链格孢菌(Alternariakikuchiana)、猕猴桃果实拟茎点霉(Phomopsis sp.)、七叶树壳梭孢菌(Fusicoccumaesculi)等。
实施例1
化合物1：3,7-二甲基-N-苯基辛-6-烯酰胺(C16H23NO)；结构式为：
制备方法为：在配有磁力搅拌装置的三口烧瓶中加入10mmol香茅酸和10ml二氯甲烷，冰浴滴加由10ml二氯甲烷溶解的20mmol草酰氯，滴加完毕后，升温至40℃，反应结束后减压蒸馏除溶剂，得香茅酰氯。再用10ml二氯甲烷溶解10mmol香茅酸酰氯，搅拌和冰水浴条件下缓慢滴加到盛有15mmol苯胺、15mmol三乙胺和10ml二氯甲烷中，滴加完毕后，无水条件下反应。反应结束后，减压蒸馏除溶剂，柱层析得香茅酸酰胺类衍生物纯品。产物表征，数据如下：
得率60.1％；FT-IR v(cm-1):3295(N-H),3200,3137,3058(Ar-H),2960,2914,2866,2846(C-H),1656(C＝O),1599,1541,1498,1441(苯环骨架),753,691(苯环单取代)；1H NMR(400MHz,CDCl3)δ7.53(d,J＝7.9Hz,2H),7.32(t,J＝7.7Hz,2H),7.11(t,J＝7.3Hz,1H),5.11(t,J＝6.6Hz,1H),2.38(dd,J＝12.7,4.6Hz,1H),2.08(d,J＝19.3Hz,3H),1.71(d,J＝13.7Hz,3H),1.61(s,2H),1.57(s,1H),1.44(d,J＝7.4Hz,1H),1.27(t,J＝7.1Hz,2H),1.01(d,J＝6.0Hz,3H).13C NMR(400MHz,CDCl3)δ171.03,138.09,131.72,129.08,124.35(d,J＝7.4Hz),120.00,45.65,37.01,30.55,25.61,22.60,19.71,17.78.HRMScalculated for C16H23NO[M+H]+246.3660,found 246.1853。
实施例2
化合物2：N-(2-氯苯基)-3,7-二甲基辛-6-烯酰胺(C16H22ClNO)，结构式为：
制备方法同实施例1，其中用2-氯苯胺替换苯胺，产物表征，数据如下：
得率65.61％，m.p.42.3～43.7℃；FT-IR v(cm-1):3283(N-H),3104,(Ar-H),2965,2904,2869,2832(C-H),1656(C＝O),1585,1527,1471,1439(苯环骨架),746(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ8.39(d,J＝8.0Hz,1H),7.37(d,J＝7.8Hz,1H),7.29(d,J＝8.2Hz,1H),7.04(t,J＝7.5Hz,1H),5.12(t,J＝6.8Hz,1H),2.46(dd,J＝14.0,5.7Hz,1H),2.27–2.17(m,1H),2.15–1.95(m,3H),1.75–1.66(m,3H),1.62(s,2H),1.58(s,1H),1.50–1.42(m,1H),1.30(dd,J＝14.4,5.8Hz,1H),1.04(d,J＝6.5Hz,3H).13C NMR(400MHz,CDCl3)δ170.94,134.76,131.80,129.06,127.84,124.63,124.28,122.70,121.82,45.81,36.93,30.69,25.82,25.59,19.75,17.80.HRMS calculated for C16H22ClNO[M+H]+280.1390,found 280.1461。
实施例3
化合物3：N-(3-氯苯基)-3,7-二甲基辛-6-烯酰胺(C16H22ClNO)，结构式为：
制备方法同实施例1，其中用3-氯苯胺替换苯胺，产物表征，数据如下：
得率53.4％；FT-IR v(cm-1):3296(N-H),3188,3122(Ar-H),2961,2914,2869,2846(C-H),1660(C＝O),1592,1533,1481,1422(苯环骨架),777,681(苯环间位取代)；1H NMR(400MHz,CDCl3)δ7.66(s,1H),7.37(d,J＝8.1Hz,1H),7.22(t,J＝8.1Hz,1H),7.07(d,J＝7.9Hz,1H),5.09(t,J＝6.6Hz,1H),2.38(dd,J＝13.5,5.3Hz,1H),2.17–1.96(m,4H),1.69(s,3H),1.58(d,J＝15.4Hz,3H),1.42(dd,J＝14.4,7.9Hz,1H),1.26(dd,J＝7.8,5.2Hz,1H),1.00(d,J＝6.3Hz,3H).13C NMR(400MHz,CDCl3)δ171.26,139.20,134.73,131.81,130.05,124.32,120.10,117.93,45.54,36.96,30.66,25.81,25.58,19.68,17.79.HRMScalculated for C16H22ClNO[M+H]+280.1390,found 280.1468。
实施例4
化合物4：N-(4-氯苯基)-3,7-二甲基辛-6-烯酰胺(C16H22ClNO)，结构式为：
制备方法同实施例1，其中用4-氯苯胺替换苯胺，产物表征，数据如下：
得率52.8％，m.p.58.5～60.9℃；FT-IR v(cm-1):3286(N-H),3182,3113,3042(Ar-H),2966,2926,2909,2848(C-H),1652(C＝O),1593,1567,1492,1451(苯环骨架),820(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.48(d,J＝8.6Hz,2H),7.29–7.26(m,2H),5.10(t,J＝6.5Hz,1H),2.37(dd,J＝13.2,5.0Hz,1H),2.14–1.99(m,4H),1.69(s,3H),1.61(s,3H),1.42(dd,J＝14.3,8.1Hz,1H),1.30–1.24(m,1H),1.00(d,J＝6.2Hz,3H).；13C NMR(400MHz,CDCl3)δ171.05,136.61,131.83,129.19,124.29,121.21,45.57,36.98,30.66,25.81,25.58,19.71,17.79.HRMS calculated for C16H22ClNO[M+H]+280.1390,found 280.1468。
实施例5
化合物5：N-(2-氟苯基)-3,7-二甲基辛-6-烯酰胺(C16H22FNO)，结构式为：
制备方法同实施例1，其中用2-氟苯胺替换苯胺，产物表征，数据如下：
得率63.86％；FT-IR v(cm-1):3277(N-H),3194,3128(Ar-H),2963,2915,2869,2852(C-H),1665(C＝O),1617,1598,1530,1489(苯环骨架),749(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ8.34(t,J＝7.8Hz,1H),7.39(s,1H),7.13–7.05(m,2H),5.11(t,J＝6.9Hz,1H),2.43(dd,J＝14.0,5.6Hz,1H),2.26–1.94(m,4H),1.82–1.66(m,3H),1.59(d,J＝16.4Hz,3H),1.49–1.40(m,1H),1.28(dd,J＝15.7,8.6Hz,1H),1.02(d,J＝6.4Hz,3H).13CNMR(400MHz,CDCl3)δ170.97,153.67,131.77,124.69,124.31,121.96,114.92,45.60,36.93,30.64,25.68,25.34,19.69,17.76.HRMS calculated for C16H22FNO[M+H]+264.1685,found 264.1747。
实施例6
化合物6：N-(3-氟苯基)-3,7-二甲基辛-6-烯酰胺(C16H22FNO)，结构式为：
制备方法同实施例1，其中用3-氟苯胺替换苯胺，产物表征，数据如下：
得率66.15％，m.p.42.1～44.5℃；FT-IR v(cm-1):3289(N-H),3200,3137(Ar-H),2953,2910,2869,2852(C-H),1654(C＝O),1603,1535,1489,1441(苯环骨架),766,681(苯环间位取代)；1H NMR(400MHz,DMSO)δ7.51(d,J＝10.9Hz,1H),7.26–7.21(m,1H),7.16(d,J＝8.0Hz,1H),6.80(t,J＝8.2Hz,1H),5.09(t,J＝6.9Hz,1H),2.38(dd,J＝13.5,5.4Hz,1H),2.18–2.00(m,4H),1.68(s,3H),1.60(s,3H),1.42(dd,J＝13.9,8.2Hz,1H),1.28–1.22(m,1H),1.00(d,J＝6.3Hz,3H).13C NMR(400MHz,CDCl3)δ171.31,164.32,139.56,130.11(d,J＝9.3Hz),124.28,115.16,111.10,110.88,45.57,36.96,30.66,25.80,25.58,19.67,17.77.HRMS calculated for C16H22FNO[M+H]+264.1685,found 264.1748。
实施例7
化合物7：N-(4-氟苯基)-3,7-二甲基辛-6-烯酰胺(C16H22FNO)，结构式为：
制备方法同实施例1，其中用4-氟苯胺替换苯胺，产物表征，数据如下：
得率66.35％，m.p.62.5～64.6℃；FT-IR v(cm-1):3274(N-H),3146,3066(Ar-H),2968,2905,2847(C-H),1654(C＝O),1612,1523,1507,1452(苯环骨架,830(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.48(dd,J＝8.7,4.7Hz,2H),7.00(t,J＝8.5Hz,2H),5.10(t,J＝6.4Hz,1H),2.37(dd,J＝12.6,4.5Hz,1H),2.16–1.97(m,4H),1.69(s,3H),1.61(s,3H),1.43(dd,J＝13.7,8.5Hz,1H),1.27(dt,J＝13.4,6.8Hz,1H),1.00(d,J＝6.0Hz,3H).13CNMR(400MHz,CDCl3)δ171.01,160.67,134.04,131.78,124.32,121.89(d,J＝7.7Hz),115.79,115.57,45.45,37.00,30.69,25.69,25.58–25.35,19.70,17.77.HRMS calculatedfor C16H22FNO[M+H]+264.1685,found 264.1753。
实施例8
化合物8：N-(2-溴苯基)-3,7-二甲基辛-6-烯酰胺(C16H22BrNO)，结构式为：
制备方法同实施例1，其中用2-溴苯胺替换苯胺，产物表征，数据如下：
得率54.47％，m.p.41.2～42.9℃；FT-IR v(cm-1):3274(N-H),3188,3104,3036(Ar-H),2967,2904,2869,2845(C-H),1656(C＝O),1580,1528,1469,1436(苯环骨架),741(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ8.38(d,J＝8.1Hz,1H),7.61(s,1H),7.55(d,J＝8.0Hz,1H),7.33(t,J＝7.8Hz,1H),6.99(t,J＝7.6Hz,1H),5.12(t,J＝6.5Hz,1H),2.46(dd,J＝14.0,5.7Hz,1H),2.28–1.99(m,4H),1.71(d,J＝10.3Hz,3H),1.62(s,3H),1.50–1.42(m,1H),1.31(dd,J＝14.1,5.7Hz,1H),1.08–1.01(m,3H).13C NMR(400MHz,CDCl3)δ170.90,135.86,132.28,131.81,128.50,125.17,124.27,122.08,113.36,45.85,36.94,30.72,25.81,25.59,19.78,17.81.HRMS calculated for C16H22BrNO[M+H]+324.0885,found 324.0954.
实施例9
化合物9：N-(3-溴苯基)-3,7-二甲基辛-6-烯酰胺(C16H22BrNO)，结构式为：
制备方法同实施例1，其中用3-溴苯胺替换苯胺，产物表征，数据如下：
得率63.75％；FT-IR v(cm-1):3292(N-H),3179,3114,3075(Ar-H),2961,2913,2872,2849(C-H),1659(C＝O),1587,1530,1476,1418(苯环骨架),776,680(苯环间位取代)；1H NMR(400MHz,CDCl3)δ7.80(s,1H),7.44(d,J＝7.9Hz,1H),7.19(dd,J＝22.8,7.9Hz,2H),5.09(t,J＝6.6Hz,1H),2.38(dd,J＝13.6,5.5Hz,1H),2.17–1.99(m,4H),1.68(s,3H),1.60(s,3H),1.41(dd,J＝14.3,8.3Hz,1H),1.28–1.22(m,1H),0.99(d,J＝6.3Hz,3H).13CNMR(400MHz,CDCl3)δ171.34,139.35,131.80,130.34,127.29,124.29,122.98,122.69,118.49,77.48,77.17,76.85,45.51,36.96,30.68,25.82,25.59,19.68,17.80.HRMScalculated for C16H22BrNO[M+H]+324.0885,found 324.0958.
实施例10
化合物10：N-(4-溴苯基)-3,7-二甲基辛-6-烯酰胺(C16H22BrNO)，结构式为：
制备方法同实施例1，其中用4-溴苯胺替换苯胺，产物表征，数据如下：
得率59.37％，m.p.85.6～87.3℃；FT-IR v(cm-1):3283,3231(N-H),3173,3110,3033(Ar-H),2965,2912,2869,2848(C-H),1650(C＝O),1590,1526,1487,1449(苯环骨架),817(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.47–7.38(m,4H),5.09(t,J＝6.5Hz,1H),2.36(dd,J＝13.3,5.1Hz,1H),2.16–1.95(m,4H),1.68(s,3H),1.58(d,J＝15.1Hz,3H),1.45–1.36(m,1H),1.30–1.21(m,1H),0.99(d,J＝6.2Hz,3H).13C NMR(400MHz,CDCl3)δ171.23,137.13,132.02,131.82,124.27,121.63,116.90,45.54,36.98,30.67,25.70,25.57–25.37(m),19.70,17.80.HRMS calculated for C16H22BrNO[M+H]+324.0885,found324.0956.
实施例11
化合物11：N-(2-碘苯基)-3,7-二甲基辛-6-烯酰胺(C16H22INO)，结构式为：
制备方法同实施例1，其中用2-碘苯胺替换苯胺，产物表征，数据如下：
得率61.2％，m.p.59.2～61.6℃；FT-IR v(cm-1):3267(N-H),3191,3140,3024(Ar-H),2961,2910,2866,2846(C-H),1655(C＝O),1575,1526,1463,1432(苯环骨架),741(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ8.24(d,J＝7.9Hz,1H),7.78(d,J＝7.9Hz,1H),7.35(t,J＝7.7Hz,1H),6.85(t,J＝7.5Hz,1H),5.12(t,J＝6.8Hz,1H),2.46(dd,J＝13.8,5.6Hz,1H),2.22–2.02(m,4H),1.70(s,3H),1.62(s,3H),1.51–1.44(m,1H),1.31(dd,J＝13.9,5.8Hz,1H),1.05(d,J＝6.5Hz,3H).13C NMR(400MHz,CDCl3)δ170.96,138.89,138.63,131.79,129.37,126.01,124.31,122.22,90.10,45.85,36.98,30.76,25.86,25.62,19.84,17.86.HRMS calculated for C16H22INO[M+H]+372.0746,found 372.0801.
实施例12
化合物12：N-(3-碘苯基)-3,7-二甲基辛-6-烯酰胺(C16H22INO)，结构式为：
制备方法同实施例1，其中用3-碘苯胺替换苯胺，产物表征，数据如下：
得率62.2％；FT-IR v(cm-1):3289,3247(N-H),3176,3108,3066(Ar-H),2960,2911,2866,2852(C-H),1658(C＝O),1581,1529,1473,1413(苯环骨架),775,681(苯环间位取代)；1H NMR(400MHz,CDCl3)δ7.94(s,1H),7.50(d,J＝8.1Hz,1H),7.46–7.39(m,2H),7.03(t,J＝8.0Hz,1H),5.10(t,J＝6.8Hz,1H),2.37(dd,J＝13.4,5.2Hz,1H),2.15–1.98(m,4H),1.69(s,3H),1.61(s,3H),1.42(dd,J＝14.5,8.0Hz,1H),1.25(dd,J＝13.7,5.2Hz,1H),1.00(d,J＝6.2Hz,3H).13C NMR(400MHz,CDCl3)δ171.11,139.20,133.33,131.82,130.55,128.65,124.29,119.14,94.22,45.55,36.97,30.66,25.83,25.59,19.71,17.81.HRMS calculated for C16H22INO[M+H]+372.0746,found 372.0799.
实施例13
化合物13：N-(4-碘苯基)-3,7-二甲基辛-6-烯酰胺(C16H22INO)，结构式为：
制备方法同实施例1，其中用4-碘苯胺替换苯胺，产物表征，数据如下：
得率59.37％,m.p.86.8～88.2℃；FT-IR v(cm-1):3292(N-H),3173,3093,3030(Ar-H),2965,2906,2869,2843(C-H),1659(C＝O),1584,1519,1485(苯环骨架),813(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.60(d,J＝8.4Hz,2H),7.31(d,J＝8.5Hz,2H),5.09(t,J＝6.6Hz,1H),2.36(dd,J＝13.3,5.0Hz,1H),2.21–1.91(m,4H),1.70(d,J＝14.5Hz,3H),1.58(d,J＝14.8Hz,3H),1.41(dd,J＝13.8,8.1Hz,1H),1.25(dd,J＝14.3,5.8Hz,1H),0.99(d,J＝6.1Hz,3H).13C NMR(400MHz,CDCl3)δ171.15,137.91,131.83,124.28,121.86,87.44,45.61,36.98,30.66,25.84,25.59,19.71,17.82.HRMS calculated for C16H22INO[M+H]+372.0746,found 372.0799.
实施例14
化合物14：N-(2-甲基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO)，结构式为：
制备方法同实施例1，其中用2-甲基苯胺替换苯胺，产物表征，数据如下：
得率38.3％，m.p.59.9～61.2℃；FT-IR v(cm-1):3273(N-H),3185,3131,3027(Ar-H),2969,2901,2869,2846(C-H),1645(C＝O),1589,1532,1486,1455(苯环骨架),749(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ7.79(d,J＝7.9Hz,1H),7.25–7.17(m,2H),7.07(dd,J＝19.1,11.6Hz,2H),5.12(s,1H),2.42(dd,J＝13.3,5.1Hz,1H),2.26(s,3H),2.21–1.99(m,4H),1.72(d,J＝16.1Hz,3H),1.60(d,J＝16.5Hz,3H),1.51–1.42(m,1H),1.30(dd,J＝14.2,8.2Hz,1H),1.04(d,J＝6.2Hz,3H).13C NMR(400MHz,CDCl3)δ170.88,135.86,131.73,130.56,129.20,126.86,125.28,124.38,123.48,45.49,37.02,30.80,25.71,25.55–25.42,19.75,17.87(d,J＝14.8Hz).HRMS calculated for C17H25NO[M+H]+260.1936,found260.1999.
实施例15
化合物15：N-(3-甲基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO)，结构式为：
制备方法同实施例1，其中用3-甲基苯胺替换苯胺，产物表征，数据如下：
得率61.48％；FT-IR v(cm-1):3293(N-H),3207,3149,3087(Ar-H),2961,2915,2869,2852(C-H),1656(C＝O),1612,1594,1488,1436(苯环骨架),778,690(苯环间位取代)；1H NMR(400MHz,CDCl3)δ7.79(d,J＝7.9Hz,1H),7.25–7.17(m,2H),7.07(dd,J＝19.1,11.6Hz,2H),5.12(s,1H),2.42(dd,J＝13.3,5.1Hz,1H),2.26(s,3H),2.21–1.99(m,4H),1.72(d,J＝16.1Hz,3H),1.60(d,J＝16.5Hz,3H),1.51–1.42(m,1H),1.30(dd,J＝14.2,8.2Hz,1H),1.04(d,J＝6.2Hz,3H).13C NMR(400MHz,CDCl3)δ171.21,138.95,138.07,131.68,128.86,125.10,124.42,120.75,117.16,45.60,37.01,30.73,25.83,25.63,21.58,19.68,17.80.HRMS calculated for C17H25NO[M+H]+260.1936,found 260.2000.
实施例16
化合物16：N-(4-甲基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO)，结构式为：
制备方法同实施例1，其中用4-甲基苯胺替换苯胺，产物表征，数据如下：
得率51.1％，m.p.35.7～37.4℃；FT-IR v(cm-1):3287(N-H),3185,3116,3033(Ar-H),2963,2916,2866,2852(C-H),1649(C＝O),1598,1515,1452,1404(苯环骨架),814(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.41(d,J＝8.2Hz,2H),7.12(d,J＝8.1Hz,2H),5.11(t,J＝6.7Hz,1H),2.39–2.34(m,1H),2.32(s,3H),2.18–1.94(m,4H),1.69(s,3H),1.59(d,J＝16.7Hz,3H),1.45(dd,J＝13.5,6.1Hz,1H),1.26(dt,J＝13.9,7.0Hz,1H),1.00(d,J＝6.0Hz,3H).13C NMR(400MHz,CDCl3)δ170.99,135.53,133.92,131.69,129.55,124.43,120.14,45.59,37.02,30.72,25.84,25.73,20.97,19.70,17.80.HRMS calculated forC17H25NO[M+H]+260.1936,found 260.2001.
实施例17
化合物17：N-(2-甲氧基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO2)，结构式为：
制备方法同实施例1，其中用2-甲氧基苯胺替换苯胺，产物表征，数据如下：
得率72.68％；FT-IR v(cm-1):3426,3324(N-H),3134(Ar-H),2962,2927,2869,2849(C-H),1679(C＝O),1600,1520,1484,1458(苯环骨架),745(苯环邻位取代)；1H NMR(400MHz,CDCl3)δ8.41(d,J＝7.8Hz,1H),7.76(s,1H),7.04(t,J＝7.5Hz,1H),6.97(t,J＝7.6Hz,1H),6.88(d,J＝8.0Hz,1H),5.12(t,J＝6.9Hz,1H),3.89(s,3H),2.46–2.37(m,1H),2.24–1.97(m,4H),1.75–1.66(m,3H),1.60(d,J＝17.2Hz,3H),1.48–1.41(m,1H),1.28(dd,J＝13.5,6.3Hz,1H),1.03(t,J＝5.5Hz,3H).13C NMR(400MHz,CDCl3)δ170.83,147.82,131.62,127.87,124.46,123.61,121.22,119.92,109.97,55.78,45.92,36.98,30.69,25.73,19.73,17.78.HRMS calculated for C17H25NO2[M+H]+276.1885,found 276.1950.
实施例18
化合物18：N-(3-甲氧基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO2)，结构式为：
制备方法同实施例1，其中用3-甲氧基苯胺替换苯胺，产物表征，数据如下：
得率65.35％；FT-IR v(cm-1):3294,3256(N-H),3203,3143,3063(Ar-H),2958,2913,2869,2849(C-H),1657(C＝O),1598,1544,1492,1453(苯环骨架),769,687(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.60(d,J＝25.2Hz,1H),7.34(s,1H),7.19(t,J＝8.1Hz,1H),6.99(d,J＝7.8Hz,1H),6.66(d,J＝8.1Hz,1H),5.10(t,J＝6.8Hz,1H),3.78(s,3H),2.37(dd,J＝12.9,4.8Hz,1H),2.18–1.95(m,4H),1.68(s,3H),1.58(d,J＝16.5Hz,3H),1.45–1.37(m,1H),1.24(dd,J＝13.7,6.1Hz,1H),1.00(d,J＝6.1Hz,3H).13C NMR(400MHz,CDCl3)δ171.27,160.26,139.38,131.70,129.71,124.38,112.10,110.20,105.71,55.38,45.66,36.99,30.68,25.72,25.60–25.37,19.68,17.79.HRMS calculated for C17H25NO2[M+H]+276.1885,found 276.1951.
实施例19
化合物19：N-(4-甲氧基苯基)-3,7-二甲基辛-6-烯酰胺(C17H25NO2)，结构式为：
制备方法同实施例1，其中用4-甲氧基苯胺替换苯胺，产物表征，数据如下：
得率56.04％，m.p.61.1～63.5℃；FT-IR v(cm-1):3294(N-H),3194,3131,3048(Ar-H),2956,2912,2852,2837(C-H),1650(C＝O),1601,1531,1512,(苯环骨架),824(苯环对位取代)；1H NMR(400MHz,CDCl3)δ7.42(d,J＝8.6Hz,2H),6.85(d,J＝8.6Hz,2H),5.11(t,J＝6.5Hz,1H),3.79(s,3H),2.34(dd,J＝10.8,6.3Hz,1H),2.19–1.89(m,4H),1.77–1.67(m,3H),1.59(d,J＝16.0Hz,3H),1.43(dd,J＝20.9,13.3Hz,1H),1.30–1.21(m,1H),1.00(d,J＝5.6Hz,3H).13C NMR(400MHz,CDCl3)δ170.88,156.49,131.70,131.19,124.42,121.96,114.24,55.60,45.46,37.03,30.73,25.82,25.62,19.71,17.79.HRMS calculatedfor C17H25NO2[M+H]+276.1885,found 276.1956.
实施例20
化合物20：3,7-二甲基-N-(2-吡啶基)辛-6-烯酰胺(C15H22N2O)，结构式为：
制备方法同实施例1，其中用2-氨基吡啶替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率45.71％；FT-IR v(cm-1):3252(N-H),3110(Ar-H),2962,2915,2871,2848(C-H),1695(C＝O),1593,1577,1523,1460(吡啶环),1431(C＝N),778(吡啶环邻位取代)；1HNMR(500MHz,DMSO)δ10.43(s,1H),8.29(dd,J＝4.8,1.2Hz,1H),8.10(d,J＝8.3Hz,1H),7.75(dd,J＝11.3,4.4Hz,1H),7.10–7.06(m,1H),5.08(t,J＝7.0Hz,1H),2.37(dd,J＝14.0,6.2Hz,1H),2.22(dd,J＝14.0,8.1Hz,1H),2.00–1.92(m,2H),1.64(s,3H),1.56(s,2H),1.33(dd,J＝15.8,6.6Hz,1H),1.18(dd,J＝12.2,8.9Hz,1H),0.90(d,J＝6.7Hz,2H).13C NMR(500MHz,DMSO)δ172.15,152.56,148.32,138.50,131.09,124.90,119.63,113.88,43.99,36.83,30.24,25.98,25.42,19.83,17.98.HRMS calculated for C15H22N2O[M+H]+247.1732,found 247.1789.
实施例21
化合物21：3,7-二甲基-N-(3-吡啶基)辛-6-烯酰胺(C15H22N2O)，结构式为：
制备方法同实施例1，其中用3-氨基吡啶替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率66.26％；FT-IR v(cm-1):3256(N-H),3179,3119,3045(Ar-H),2959,2914,2869,2852(C-H),1661(C＝O),1596,1581,1537,1480(吡啶环),1418(C＝N),805,701(吡啶环间位取代)；1H NMR(400MHz,CDCl3)δ7.42(d,J＝8.6Hz,2H),6.85(d,J＝8.6Hz,2H),5.11(t,J＝6.5Hz,1H),3.79(s,3H),2.34(dd,J＝10.8,6.3Hz,1H),2.19–1.89(m,4H),1.77–1.67(m,3H),1.59(d,J＝16.0Hz,3H),1.43(dd,J＝20.9,13.3Hz,1H),1.30–1.21(m,1H),1.00(d,J＝5.6Hz,3H).13C NMR(400MHz,CDCl3)δ172.17,144.67,141.10,135.66,131.72,127.63,124.28,124.10(d,J＝31.2Hz),45.16,36.99,30.62,25.82,25.67,19.65,17.76.HRMS calculated for C15H22N2O[M+H]+247.1732,found 247.1792.
实施例22
化合物22：3,7-二甲基-N-(4-吡啶基)辛-6-烯酰胺(C15H22N2O)，结构式为：
制备方法同实施例1，其中用4-氨基吡啶替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率58.25％；FT-IR v(cm-1):3238(N-H),3158,3072(Ar-H),2962,2913,2869,2849(C-H),1679(C＝O),1589,1510(吡啶环),1415(C＝N),826(吡啶环对位取代)；1H NMR(400MHz,CDCl3)δ8.45(d,J＝6.0Hz,2H),7.57(d,J＝6.1Hz,2H),5.07(t,J＝6.9Hz,1H),2.41(dd,J＝14.1,5.8Hz,1H),2.18(dd,J＝14.1,8.3Hz,1H),2.10–1.96(m,3H),1.66(s,3H),1.58(s,3H),1.43–1.36(m,1H),1.27–1.21(m,1H),0.98(d,J＝6.5Hz,3H).13C NMR(400MHz,CDCl3)δ172.31,150.38,145.85,131.85,124.19,113.86,45.46,36.95,30.54,25.81,25.54,19.67,17.77.HRMS calculated for C15H22N2O[M+H]+247.1732,found247.1791.
实施例23
化合物23：3,7-二甲基-N-(2-噻唑基)辛-6-烯酰胺(C13H20N2OS)，结构式为：
制备方法同实施例1，其中用2-氨基噻唑替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率40.35％，m.p.32.7～34.1℃；FT-IR v(cm-1):3259,3166(N-H),2959,2915,2852(C-H),1679(C＝O),1555(C＝N),1183,1166(C-S-C)；1H NMR(400MHz,CDCl3)δ12.19(s,1H),7.45(d,J＝3.6Hz,1H),7.02(d,J＝3.6Hz,1H),5.10(t,J＝6.9Hz,1H),2.57(dd,J＝14.3,5.9Hz,1H),2.36(dd,J＝14.3,8.4Hz,1H),2.18–1.98(m,3H),1.68(s,3H),1.60(s,3H),1.51–1.42(m,1H),1.31(dd,J＝14.3,8.5Hz,1H),1.02(d,J＝6.6Hz,3H)；13C NMR(400MHz,CDCl3)δ170.65,159.85,136.30,131.79,124.06,113.48,43.90,36.93,30.25,25.68,25.43,19.56,17.66.HRMS calculated for C13H20N2OS[M+H]+253.1292,found253.1358.
实施例24
化合物24：3,7-二甲基-N-(2-苯并噻唑基)辛-6-烯酰胺(C17H22N2OS)，结构式为：
制备方法同实施例1，其中用2-氨基苯并噻唑替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率75.21％，m.p.103.7～105.1℃；FT-IR v(cm-1):3214(N-H),3168,3059(Ar-H),2970,2910,2869,2847(C-H),1656(C＝O),1596(C＝N),1538,1468,1453,1437(苯环骨架),1304,1257(C-S-C)；1H NMR(400MHz,CDCl3)δ11.39(s,1H),7.76(d,J＝7.9Hz,1H),7.69(d,J＝8.1Hz,1H),7.37(t,J＝7.5Hz,1H),7.24(t,J＝7.5Hz,1H),4.89(t,J＝6.8Hz,1H),2.38(dd,J＝14.4,5.9Hz,1H),2.20–2.13(m,1H),1.92(dd,J＝13.0,6.5Hz,1H),1.77(dd,J＝15.7,6.5Hz,2H),1.55(s,3H),1.44(s,3H),1.16(s,1H),1.01(dd,J＝13.9,5.5Hz,1H),0.78(d,J＝6.6Hz,3H).13C NMR(400MHz,CDCl3)δ170.43,158.66,146.75,130.93,130.81,125.30,122.98,120.63,119.43,42.97,35.63,29.23,24.66,18.34,16.62.HRMScalculated for C17H22N2OS[M+H]+303.1453,found 303.1516.
实施例25
化合物25：N-(3-氰基噻吩-2-基)-3,7-二甲基辛-6-烯酰胺(C15H20N2OS)，结构式为：
制备方法同实施例1，其中用2-氨基-3-氰基噻吩替换苯胺，步骤2)中二氯甲烷替换为乙腈，对产物表征，数据如下：
得率30.72％,m.p.79.7～81.2℃；FT-IR v(cm-1):3259,3221(N-H),2967,2914,2873,2852(C-H),2226(C≡N),1680(C＝O),1203,1152(C-S-C)；1H NMR(400MHz,CDCl3)δ9.20(s,1H),6.99(d,J＝5.8Hz,1H),6.86(d,J＝5.7Hz,1H),5.11(t,J＝7.0Hz,1H),2.55(dd,J＝14.5,5.8Hz,1H),2.33(dd,J＝14.5,8.3Hz,1H),2.16–2.00(m,3H),1.69(s,3H),1.62(s,3H),1.49–1.42(m,1H),1.31(dd,J＝14.0,5.7Hz,1H),1.03(d,J＝6.6Hz,3H)；13CNMR(400MHz,CDCl3)δ170.07,150.01,131.80,124.06,123.71,118.14,114.82,92.09,43.52,36.80,30.45,25.70,25.44,19.56,17.69.HRMS calculated for C15H20N2OS[M+H]+277.1296,found 277.1371.
实施例26
化合物26：3,7-二甲基-N-(喹啉-2-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用2-氨基喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率29.18％；FT-IR v(cm-1):3265(N-H),2962,2913,2869,2849(C-H),1697(C＝O),1620(C＝N),1598,1581,1521,1497(喹啉环C＝C的伸缩振动)；1H NMR(400MHz,CDCl3)δ9.01(s,1H),8.48(d,J＝8.8Hz,1H),8.18(d,J＝9.0Hz,1H),7.83(d,J＝8.4Hz,1H),7.78(d,J＝8.0Hz,1H),7.66(t,J＝7.6Hz,1H),7.45(t,J＝7.4Hz,1H),5.06(t,J＝7.0Hz,1H),2.42(dd,J＝13.7,5.3Hz,1H),2.16(t,J＝6.9Hz,1H),2.13–2.08(m,1H),1.99–1.92(m,2H),1.67(s,3H),1.57(s,3H),1.35(dd,J＝12.7,6.4Hz,1H),1.25–1.18(m,1H),0.96(d,J＝6.4Hz,3H).13C NMR(400MHz,CDCl3)δ171.47,150.80,145.97,138.17,131.11,129.52,127.15,126.69,125.83,124.51,123.68,114.06,45.00,36.34,29.95,25.22,24.92,19.01,17.18.HRMS calculated for C19H24N2O[M+H]+297.1889,found 297.1933.
实施例27
化合物27：3,7-二甲基-N-(喹啉-3-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用3-氨基喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率40.75％；FT-IR v(cm-1):3248(N-H),2958,2911,2875,2849(C-H),1662(C＝O),1618(C＝N),1580,1561,1497,1469(喹啉环C＝C的伸缩振动)；1H NMR(400MHz,CDCl3)δ8.82(s,1H),8.74(d,J＝2.2Hz,1H),8.03(d,J＝8.4Hz,1H),7.80(d,J＝8.1Hz,1H),7.63(t,J＝7.4Hz,1H),7.54(t,J＝7.5Hz,1H),5.11(t,J＝7.0Hz,1H),2.48(dd,J＝14.0,5.8Hz,1H),2.24(dd,J＝14.0,8.3Hz,1H),2.14–2.01(m,3H),1.69(s,3H),1.61(s,3H),1.46(dd,J＝14.3,8.0Hz,1H),1.28(d,J＝7.2Hz,1H),1.04(d,J＝6.5Hz,3H)；13C NMR(400MHz,CDCl3)δ171.63,145.17,143.85,131.67(d,J＝21.3Hz),128.92,128.26,127.77,127.27,124.03,45.36,36.87,30.57,25.59,25.32,19.64,17.69.HRMS calculated forC19H24N2O[M+H]+297.1889,found 297.1943.
实施例28
化合物28：3,7-二甲基-N-(喹啉-5-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用5-氨基喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率31.15％，m.p.51.7～53.5℃；FT-IR v(cm-1):3257(N-H),2962,2909,2869,2855(C-H),1649(C＝O),1622(C＝N),1595,1571,1532,1493(喹啉环C＝C的伸缩振动)；1HNMR(400MHz,CDCl3)δ8.91(d,J＝2.9Hz,1H),8.17(d,J＝8.3Hz,1H),7.97(d,J＝8.4Hz,1H),7.78(d,J＝7.4Hz,1H),7.69(s,1H),7.39(dd,J＝8.5,4.0Hz,1H),5.13(s,1H),2.52(dd,J＝13.9,5.8Hz,1H),2.27(dd,J＝13.8,8.3Hz,1H),2.14–2.01(m,3H),1.70(s,3H),1.63(s,3H),1.25(d,J＝6.1Hz,1H),1.07(d,J＝6.4Hz,3H).13C NMR(400MHz,CDCl3)δ171.66,150.36,148.67,132.63(d,J＝27.8Hz),132.10(d,J＝67.2Hz),130.07,129.18,127.63,124.16,123.15,122.21,120.95,45.06,36.95,30.69,25.60,25.48–25.24,19.72,17.70.HRMS calculated for C19H24N2O[M+H]+297.1889,found 297.1946.
实施例29
化合物29：3,7-二甲基-N-(喹啉-6-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用6-氨基喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率21.79％；FT-IR v(cm-1):3276(N-H),2961,2913,2866,2846(C-H),1663(C＝O),1624(C＝N),1602,1577,1549,1498(喹啉环C＝C的伸缩振动)；1H NMR(400MHz,CDCl3)δ8.82(dd,J＝4.2,1.5Hz,1H),8.45(d,J＝2.0Hz,1H),8.09(s,1H),8.01(d,J＝9.0Hz,1H),7.56(dd,J＝9.0,2.3Hz,1H),7.37(dd,J＝8.3,4.2Hz,1H),5.09(t,J＝7.0Hz,1H),2.45(dd,J＝13.8,5.7Hz,1H),2.19(d,J＝9.4Hz,1H),2.10–1.97(m,3H),1.67(s,3H),1.59(s,3H),1.47–1.39(m,1H),1.28–1.23(m,1H),1.02(d,J＝6.5Hz,3H).13C NMR(400MHz,CDCl3)δ171.58,149.37,145.52,136.09,131.81,130.08,129.00,124.29,123.36,121.76,116.23,45.61,37.00,30.72,25.83,25.60,19.73,17.80.HRMS calculated for C19H24N2O[M+H]+297.1889,found 297.1944.
实施例30
化合物30：3,7-二甲基-N-(异喹啉-3-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用3-氨基异喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率35.78％；FT-IR v(cm-1):3258(N-H),2961,2914,2869,2849(C-H),1690(C＝O),1628(C＝N),1594,1524,1487,1449(喹啉环C＝C的伸缩振动)；1H NMR(400MHz,CDCl3)δ8.98(s,1H),8.61(s,1H),7.89(d,J＝8.1Hz,1H),7.82(d,J＝8.3Hz,1H),7.65(t,J＝7.6Hz,1H),7.48(t,J＝7.5Hz,1H),5.11(t,J＝7.0Hz,1H),2.48(dd,J＝13.9,5.6Hz,1H),2.22(dd,J＝13.8,8.4Hz,1H),2.10–1.99(m,3H),1.69(s,3H),1.61(s,3H),1.49–1.42(m,1H),1.26(d,J＝7.0Hz,1H),1.04(d,J＝6.5Hz,3H)；13C NMR(400MHz,CDCl3)δ171.14,152.97,150.98,138.01,130.77,127.40,126.85,126.50,125.75,124.22,120.61,107.86,45.60,36.90,30.56,25.70,25.51,19.62,17.68.HRMS calculated for C19H24N2O[M+H]+297.1889,found 297.1938.
实施例31
化合物31：3,7-二甲基-N-(异喹啉-4-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用4-氨基异喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率38.89％，m.p.76.7～80.4℃；FT-IR v(cm-1):3252(N-H),2962,2912,2866,2852(C-H),1648(C＝O),1627(C＝N),1589,1534,1497,1453(喹啉环C＝C的伸缩振动)；1HNMR(400MHz,CDCl3)δ9.07(s,1H),8.78(s,1H),7.96(d,J＝8.2Hz,1H),7.82(s,1H),7.70(t,J＝7.6Hz,1H),7.60(t,J＝7.4Hz,1H),5.13(s,1H),2.54(dd,J＝13.9,5.9Hz,1H),2.30(dd,J＝14.0,8.4Hz,1H),2.06(s,3H),1.69(s,3H),1.62(s,3H),1.49(dd,J＝14.1,7.8Hz,1H),1.32(dd,J＝13.6,5.5Hz,1H),1.08(d,J＝6.5Hz,3H)；13C NMR(400MHz,CDCl3)δ171.94,150.27,139.01,131.86,130.75(d,J＝7.9Hz),128.88,128.47-127.37,127.37-127.06,124.30,120.85,45.02,37.06,30.78,25.83,25.60,19.82,17.82.HRMScalculated for C19H24N2O[M+H]+297.1889,found 297.1942.
实施例32
化合物32：3,7-二甲基-N-(异喹啉-5-基)辛-6-烯酰胺(C19H24N2O)，结构式为：
制备方法同实施例1，其中用5-氨基异喹啉替换苯胺，步骤2)中二氯甲烷替换为乙腈，并加入催化剂量DMAP，对产物表征，数据如下：
得率40.39％，m.p.98.7～101.2℃；FT-IR v(cm-1):3263(N-H),2962,2908,2866,2844(C-H),1648(C＝O),1626(C＝N),1588,1572,1523,1483(喹啉环C＝C的伸缩振动)；1HNMR(400MHz,CDCl3)δ8.98(s,1H),8.61(s,1H),7.89(d,J＝8.1Hz,1H),7.82(d,J＝8.3Hz,1H),7.65(t,J＝7.6Hz,1H),7.48(t,J＝7.5Hz,1H),5.11(t,J＝7.0Hz,1H),2.48(dd,J＝13.9,5.6Hz,1H),2.22(dd,J＝13.8,8.4Hz,1H),2.10–1.99(m,3H),1.69(s,3H),1.61(s,3H),1.49–1.42(m,1H),1.26(d,J＝7.0Hz,1H),1.04(d,J＝6.5Hz,3H).13C NMR(400MHz,CDCl3)δ170.48,151.97,142.15,130.74,128.77,128.02,126.23,123.93,123.12,112.93,44.16,35.91,29.67,24.66,24.46,18.68,16.66.HRMS calculated for C19H24N2O[M+H]+297.1889,found 297.1951.
实施例33：香茅酸酰胺类衍生物对油茶炭疽病菌(Colletotrichumgloeosporioides)的抑制活性研究
采用菌丝生长速率法测定香茅酸酰胺类衍生物对油茶炭疽病菌(Colletotrichumgloeosporioides)的半抑制浓度(IC50)。具体如下：
在无菌的条件下，将化合物配制成浓度为10000mg/L的溶液，按一定的比例加入到经灭菌处理的马铃薯葡萄糖琼脂培养基中，得到最终浓度为250mg/L,125mg/L,62.5mg/L,31.25mg/L,15.625mg/L,7.8125mg/L的含药培养基平板。取已活化且培养好的病原菌菌饼(直径5mm)，接到上述含药培养基平板上，每个培养皿上接一个菌饼，菌饼置于培养皿中央，重复3次。以未添加任何化合物的PDA培养基平板作为空白对照组，百菌清为阳性对照。当空白对照组平板的菌落直径生长到整个培养皿的三分之二左右，用十字交叉法测量直径，取平均值，计算其抑制率，计算公式如下：
菌落直径＝菌落平均直径－菌饼直径(5mm)
菌丝生长抑制率＝[(对照菌落生长直径－处理菌落生长直径)/对照菌落生长直径]×100％
将抑制率导入SPSS软件，计算出半抑制浓度(IC50)。
本发明的香茅酸酰胺类衍生物对油茶炭疽病菌(Colletotrichumgloeosporioides)的抑制IC50值见表1。
表1香茅酸酰胺类衍生物的抑菌活性
由表1可以看出，大部分衍生物对于油茶炭疽病菌(Colletotrichumgloeosporioides)的半抑制浓度IC50值与市售农药百菌清相当，其中一部分化合物的抑菌作用显著优于百菌清，分别是化合物6、7、8、11、16、17、20、26、29。在这些化合物中，化合物6对油茶炭疽病菌(Colletotrichum gloeosporioides)的抑制效果最好，其半抑制浓度IC50值为21.177mg/L。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围。
Claims (10)
1.一种香茅酸酰胺类衍生物，其特征在于，化学结构通式为：
2.根据权利要求1所述的香茅酸酰胺类衍生物，其特征在于，R1表示任选被取代的C6芳基时，化学式为：
3.一种香茅酸酰胺类衍生物的制备方法，其特征在于，步骤如下：
步骤一：将香茅酸溶于有机溶剂中，冰浴滴加由有机溶剂溶解的酰氯化试剂，滴加完毕后，升温至30～60℃，反应结束后减压蒸馏除溶剂，得香茅酰氯；
步骤二：将香茅酸酰氯溶于有机溶剂中，冰水浴条件下搅拌，搅拌后缓慢滴加到盛有芳胺、三乙胺和有机溶剂的容器中，滴加完毕后，升温至50～80℃进行反应，反应结束后，减压蒸馏除溶剂，柱层析得香茅酸酰胺类衍生物纯品，反应式如下：
式中，R1表示任选被取代的C6芳基、杂芳基或杂环基。
4.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤一中，香茅酸与酰氯化试剂的摩尔比为1:1.5～1:2。
5.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤一中，酰氯化试剂为草酰氯和二甲亚砜中任意一种。
6.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤一中，以GC跟踪反应，显示至少一种原料消失，为反应结束。
7.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤二中，香茅酰氯与芳胺的摩尔比为1:1.5～1:2。
8.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤一和步骤二中，所述溶剂为二氯甲烷、三氯甲烷、四氯化碳或乙腈中任意一种。
9.根据权利要求3所述的香茅酸酰胺类衍生物的制备方法，其特征在于，步骤二中，以TLC跟踪反应，显示至少一种原料消失，为反应结束。
10.一种香茅酸酰胺类衍生物的应用，其特征在于，所述香茅酸酰胺类衍生物用作抗菌剂，所述抗菌剂适用于各种植物病原真菌，例如，子囊菌亚门，包括油菜菌核病菌(Sclerotinia sclerotirum)、莴苣菌核病病原菌(Lettuce sclerotinia)、辣椒菌核病病原菌(Sclerotinia sclerotiorum(Libert)de Bery)、小麦白粉病菌(Erysiphegraminis)、黄瓜白粉病菌(Sphaerotheca fuligenea)、小麦赤霉病菌(Gibberella zea)、苹果轮纹病菌(Botryosphaeria berengeriana)、小麦全蚀病菌(Gaeumanomycesgraminis var)、层出镰刀菌(Fusariumproliferatum)、毛竹枯梢病病原菌(Ceratosphaeriaphyllostachydissp.nov.)等；担子菌亚门，包括水稻纹枯病菌(Rhizoctonia solani)、小麦纹枯病菌(Rhizoctonia solani)等；鞭毛菌亚门，包括烟草黑胫病菌(Phytophthora parasitica)、辣椒疫霉病菌(Phytophthora capsici)、黄瓜霜霉病菌(Pseudoperonospora cubensis)、马铃薯晚疫病菌(Phytophthora infestans)等；半知菌亚门，包括油茶炭疽病菌(Colletotrichum gloeosporioides)、黄瓜炭疽病菌(Colletotrichum lagenarium)、辣椒炭疽病菌(Colletotrichum capsici)、枇杷炭疽病病原菌(Colletotrichum acutatum)、蕃茄早疫病菌(Alternaria solani)、玉米小斑病菌(Helminthosporum maydis)、柑桔青霉病菌(Penicillium italicum)柑桔蒂腐病菌(Diaporthe medusae)、烟草赤星病菌(Alternaria alternata)、棉花枯萎病菌(Fusarium)、香蕉叶斑病菌(Helminthosporiumtorulosum)、小麦根腐病菌(Bipolaris sorokiniana)、水稻稻瘟病菌(Pyriculariaoryzae)、花生褐斑病菌(Cercospora arachidicola)、稻曲病菌(Ustilaginoideavirens)、黄瓜灰霉病菌(Botrytis cinerea oxysporum)、棉花红腐病菌(Fusariummoniliforme)、梨链格孢菌(Alternaria kikuchiana)、猕猴桃果实拟茎点霉(Phomopsissp.)、七叶树壳梭孢菌(Fusicoccum aesculi)等。
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