4-(3,5-dichloro-2-hydroxy-phenyl)-but-3-en-2-one | 125094-31-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(3,5-dichloro-2-hydroxy-phenyl)-but-3-en-2-one
• 英文别名: (E)-4-(3,5-dichloro-2-hydroxyphenyl)but-3-en-2-one
• CAS: 125094-31-7
• 化学式: C₁₀H₈Cl₂O₂
• 分子量: 231.078
• InChiKey: HKNVYZMNEFCDPR-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氰胺 、 4-(3,5-dichloro-2-hydroxy-phenyl)-but-3-en-2-one 在 哌啶 作用下， 以 乙二醇二甲醚 为溶剂， 以19%的产率得到4,6-dichloro-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：

  丙酮 、 3,5-二氯水杨醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 以95%的产率得到4-(3,5-dichloro-2-hydroxy-phenyl)-but-3-en-2-one
  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

• Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors
  作者：Bruce L. Finkelstein、Eric A. Benner、Maura C. Hendrixson、Kevin T. Kranis、James J. Rauh、Maya R. Sethuraman、Stephen F. McCann

  DOI：10.1016/s0968-0896(01)00326-1

  日期：2002.3

  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.