5-Acetyl-2-(4-allyl-2-methoxyphenoxy) pyridine | 1809098-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Acetyl-2-(4-allyl-2-methoxyphenoxy) pyridine
• 英文别名: 1-[6-(2-methoxy-4-prop-2-enylphenoxy)pyridin-3-yl]ethanone
• CAS: 1809098-73-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: LXHJEIACIJEARM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Acetyl-2-(4-allyl-2-methoxyphenoxy) pyridine 、 4-amino-6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以49%的产率得到(E)-6-methyl-[4-[1-(6-(4-allyl-2-methoxyphenoxy)pyridin-3-yl)ethylidene]amino]-4,5-dihydro-1,2,4-triazin-3(2H)-one
  参考文献：
  名称：

  Additive effects on the improvement of insecticidal activity: Design, synthesis, and insecticidal activity of novel pymetrozine derivatives

  摘要：

  A series of new pymetrozine analogues containing both methyl on the imine carbon and phenoxy group at the pyridine ring were designed and synthesized. Their insecticidal activities against bean aphid (Aphis craccivora), mosquito larvae (Culex pipiens pallens), cotton bollworm (Helicoverpa armigera), corn borer (Ostrinia nubilalis) and oriental armyworm (Mythimna separata) were evaluated. The results of bioassays indicated that most of the target compounds showed good insecticidal activity against bean aphid; especially, IIIf (80%) and IIIl (80%) exhibited higher aphicidal activity than pymetrozine (30%) at 5 mg/kg, and the two compounds still showed 20% and 30% mortality at 2.5 mg/kg, respectively, whereas pymetrozine displayed no activity at the same concentration. These compounds exhibited a completely different structure-activity relationship to that of known pymetrozine derivatives, in which it is thought introducing alkyl group on the imine carbon could be detrimental to the activities. Our new result suggested that the methyl on the imine carbon and phenoxy group at the pyridine ring of phenoxy group may play additive effects on the improvement of aphicidal activity. Besides this, compound IIIs, containing an allyl at the para position of phenoxy group, exhibited excellent insecticidal activity against mosquito larvae, lepidoptera pests cotton bollworm, corn borer and oriental armyworm. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.017
• 作为产物：
  描述：

  丁香酚 、 2-氯-5-乙酰基吡啶 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-Acetyl-2-(4-allyl-2-methoxyphenoxy) pyridine
  参考文献：
  名称：

  “插件分子”法在新型甲氧基丙烯酸酯类杀菌剂筛选中的应用

  摘要：

  基于“插件分子”方法，设计、合成并筛选了一系列具有芳氧基吡啶基-1-乙酮肟侧链的新型甲氧基丙烯酸酯衍生物。生物活性实验表明，它们对植物病原菌，特别是核盘菌具有优良的杀菌作用。化合物5-01和5-09具有显着的杀菌活性和较广的杀菌谱。构效关系表明，顺式构型、增加药效基团数量、吡啶环2位的取代以及苯环上氯原子的引入均不利于该类化合物的杀菌活性。 3D-QSAR模型表明在苯环4位引入大的正电基团和在苯环2位引入小负电基团有利于杀菌活性，设计了化合物6 。与嘧菌酯相比，化合物6-02对核盘菌( Sclerotinia sclerotiorum (Lib.) de Bary)具有更有效的杀菌作用。细胞毒性试验和透射电镜结果表明，“插件分子”方法对嗜球果伞素类杀菌剂进行修饰，不会影响其毒性和作用机制。 “插件分子”方法是筛选高活性化合物的有效方法，对于创造新的农药分子具有重要的指导意义。

  DOI：

  10.1039/d0ra06263d

文献信息

• The application of “plug-in molecules” method in novel strobilurin fungicides screening
  作者：Xuelian Liu、Dongyan Yang、Fahong Yin、Jia-Qi Li、Yumei Xiao、Bin Fu、Zhaohai Qin

  DOI：10.1039/d0ra06263d

  日期：——

  molecular” method, a series of novel strobilurin derivatives with aryloxypyridinyl-1-ethanone oxime side chains were designed, synthesized, and screened. The biological activity experiment showed that they had an excellent fungicidal effect on plant pathogens, especially Sclerotinia sclerotiorum. Compounds 5-01 and 5-09 had significant fungicidal activity and broad fungicidal spectrum. The structure–activity

  基于“插件分子”方法，设计、合成并筛选了一系列具有芳氧基吡啶基-1-乙酮肟侧链的新型甲氧基丙烯酸酯衍生物。生物活性实验表明，它们对植物病原菌，特别是核盘菌具有优良的杀菌作用。化合物5-01和5-09具有显着的杀菌活性和较广的杀菌谱。构效关系表明，顺式构型、增加药效基团数量、吡啶环2位的取代以及苯环上氯原子的引入均不利于该类化合物的杀菌活性。 3D-QSAR模型表明在苯环4位引入大的正电基团和在苯环2位引入小负电基团有利于杀菌活性，设计了化合物6 。与嘧菌酯相比，化合物6-02对核盘菌( Sclerotinia sclerotiorum (Lib.) de Bary)具有更有效的杀菌作用。细胞毒性试验和透射电镜结果表明，“插件分子”方法对嗜球果伞素类杀菌剂进行修饰，不会影响其毒性和作用机制。 “插件分子”方法是筛选高活性化合物的有效方法，对于创造新的农药分子具有重要的指导意义。
• Additive effects on the improvement of insecticidal activity: Design, synthesis, and insecticidal activity of novel pymetrozine derivatives
  作者：Yan Yang、Yuxiu Liu、Hongjian Song、Yongqiang Li、Qingmin Wang

  DOI：10.1016/j.bmc.2015.08.017

  日期：2016.2

  A series of new pymetrozine analogues containing both methyl on the imine carbon and phenoxy group at the pyridine ring were designed and synthesized. Their insecticidal activities against bean aphid (Aphis craccivora), mosquito larvae (Culex pipiens pallens), cotton bollworm (Helicoverpa armigera), corn borer (Ostrinia nubilalis) and oriental armyworm (Mythimna separata) were evaluated. The results of bioassays indicated that most of the target compounds showed good insecticidal activity against bean aphid; especially, IIIf (80%) and IIIl (80%) exhibited higher aphicidal activity than pymetrozine (30%) at 5 mg/kg, and the two compounds still showed 20% and 30% mortality at 2.5 mg/kg, respectively, whereas pymetrozine displayed no activity at the same concentration. These compounds exhibited a completely different structure-activity relationship to that of known pymetrozine derivatives, in which it is thought introducing alkyl group on the imine carbon could be detrimental to the activities. Our new result suggested that the methyl on the imine carbon and phenoxy group at the pyridine ring of phenoxy group may play additive effects on the improvement of aphicidal activity. Besides this, compound IIIs, containing an allyl at the para position of phenoxy group, exhibited excellent insecticidal activity against mosquito larvae, lepidoptera pests cotton bollworm, corn borer and oriental armyworm. (C) 2015 Elsevier Ltd. All rights reserved.