9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene cyanamide | 118733-95-2

• 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-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-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6,11-tetraen-11-yl)cyanamide
• CAS: 118733-95-2
• 化学式: C₁₂H₁₂N₄O
• 分子量: 228.253
• InChiKey: FYHPSEVPZYGTOI-UHFFFAOYSA-N

物化性质

• 沸点：
  353.3±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 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：
  69.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯丙炔 、 9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene cyanamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到9-methyl-12-prop-2-ynyl-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：

  氰胺 、 (E)-4-(2-hydroxyphenyl)but-3-en-2-one 在 哌啶 作用下， 以 乙二醇二甲醚 为溶剂， 反应 6.0h， 以63%的产率得到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

文献信息

• Conformationally locked heterocycles. Structure of a doubly bridged pyrimido[1,2-<i>a</i>]pyrimidine from the hantzsch synthesis with 4-(2-hydroxyphenyl)but-3-en-2-one
  作者：Jan Světlík、Tibor Liptaj、FrantiŠEk Tureček

  DOI：10.1002/jhet.5570360132

  日期：1999.1

  spectroscopy was used to assign the structure to the minor product from cyclocondensation of 4-(2-hydroxyphenyl)but-3-en-2-one with cyanamide, which was identified as (6R*, 9R*, 15R*, 17R*)-6,9-dimethyl-6,17:9,15-dimemano-6H,15H,17H-[1,3,5]benzoxadiazocino[4,5-d][1,3,5]benzoxadiazocine-7(9H)-carbonitrile, a doubly oxygen-bridged pyrimido[1,2-a]pyrimidine derivative. The observed stereose lectivity and reaction

  使用1D和2D nmr光谱将结构归因于4-（2-羟苯基）but-3-en-2-one与氰酰胺的环缩合反应生成的次要产物，其鉴定为（6 R *，9 R *， 15 R *，17 R *）-6,9-二甲基-6,17：9,15-dimemano-6 H，15 H，17 H- [1,3,5] benzoxadiazocino [4,5- d ] [ 1,3,5]苯并恶二唑啉-7（9 H）-腈，一种双氧桥联嘧啶并[1,2- a ]嘧啶衍生物。借助分子力学和半经验PM3计算讨论了观察到的立体选择性和反应机理。