5,8-Dichlorophthalazine | 103119-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,8-Dichlorophthalazine
• CAS: 103119-79-5
• 化学式: C₈H₄Cl₂N₂
• 分子量: 199.039
• InChiKey: VHEHTJSHDVGEKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲硅氧基-2-呋喃 、 5,8-Dichlorophthalazine 在 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 36.0h， 以98%的产率得到4,7-dichloro-1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid

  摘要：

  A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.

  DOI：

  10.1021/ja308858y
• 作为产物：
  描述：

  2-溴-1,4-二氯苯 、 N,N-二甲基甲酰胺 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 3.17h， 以55%的产率得到5,8-Dichlorophthalazine
  参考文献：
  名称：

  Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid

  摘要：

  A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.

  DOI：

  10.1021/ja308858y

文献信息

• Domino Inverse Electron-Demand Diels–Alder/Cyclopropanation Reaction of Diazines Catalyzed by a Bidentate Lewis Acid
  作者：Simon N. Kessler、Markus Neuburger、Hermann A. Wegner

  DOI：10.1021/ja308858y

  日期：2012.10.31

  A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.