9-methyl-4-nitro-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide | 243460-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-methyl-4-nitro-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide
• 英文别名: (9-Methyl-4-nitro-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2(7),3,5,11-tetraen-11-yl)cyanamide
• CAS: 243460-57-3
• 化学式: C₁₂H₁₁N₅O₃
• 分子量: 273.251
• InChiKey: SAERLPDOTYRYDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-methyl-4-nitro-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以55%的产率得到4-amino-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide
  参考文献：
  名称：

  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors

  摘要：

  Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH2) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC50 values comparable to the organophosphate Paraoxon. Unlike organophosphates. cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00326-1
• 作为产物：
  描述：

  5-硝基水杨醛 在 哌啶 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 9-methyl-4-nitro-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide
  参考文献：
  名称：

  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors

  摘要：

  Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH2) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC50 values comparable to the organophosphate Paraoxon. Unlike organophosphates. cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00326-1