1-[4-hydroxy-3-(2,2,2-trinitroethyl)phenyl]ethanone | 1541175-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-hydroxy-3-(2,2,2-trinitroethyl)phenyl]ethanone
• CAS: 1541175-12-5
• 化学式: C₁₀H₉N₃O₈
• 分子量: 299.197
• InChiKey: VFTKRFPSQNVQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  166.72
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-[4-hydroxy-3-(2,2,2-trinitroethyl)phenyl]ethanone 以 二甲基亚砜 为溶剂， 反应 120.0h， 以40%的产率得到5-acetyl-2,2-dinitro-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Potassium Trinitromethanide as a 1,1-Ambiphilic Synthon Equivalent: Access to 2-Nitroarenofurans

  摘要：

  The first example of the use of potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine has been developed. The method tolerates a variety of functional groups on the starting quaternary ammonium salt and has been successfully extended to polysubstituted benzofurans. Formation of an o-quinone methide intermediate is postulated as a key to the mechanism of this cascade process.

  DOI：

  10.1021/jo402543s
• 作为产物：
  描述：

  3’-氯甲基-4’-羟基苯乙酮 、 三硝基甲烷钾 以 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到1-[4-hydroxy-3-(2,2,2-trinitroethyl)phenyl]ethanone
  参考文献：
  名称：

  Potassium Trinitromethanide as a 1,1-Ambiphilic Synthon Equivalent: Access to 2-Nitroarenofurans

  摘要：

  The first example of the use of potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine has been developed. The method tolerates a variety of functional groups on the starting quaternary ammonium salt and has been successfully extended to polysubstituted benzofurans. Formation of an o-quinone methide intermediate is postulated as a key to the mechanism of this cascade process.

  DOI：

  10.1021/jo402543s