4-iodo-2-nitrodibenzofuran | 1357581-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-iodo-2-nitrodibenzofuran
• CAS: 1357581-62-4
• 化学式: C₁₂H₆INO₃
• 分子量: 339.089
• InChiKey: JRYZYQJSYUDKNW-UHFFFAOYSA-N

物化性质

• 沸点：
  445.0±25.0 °C(Predicted)
• 密度：
  1.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-2-nitrodibenzofuran 在 盐酸 、 铁粉 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以63%的产率得到2-amino-4-iododibenzofuran
  参考文献：
  名称：

  CuI-Mediated Sequential Iodination/Cycloetherification of o-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies

  摘要：

  An efficient synthesis of 2- or 4-iododibenzofurans through Cul-mediated sequential iodination/cycloetherification of two aromatic C-H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO2, CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C-H activation step is involved in cycloetherification.

  DOI：

  10.1021/ol302562a
• 作为产物：
  描述：

  4-硝基-2-苯基苯酚 在 copper(l) iodide 、 氧气 、 三甲基乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到4-iodo-2-nitrodibenzofuran
  参考文献：
  名称：

  CuI-Mediated Sequential Iodination/Cycloetherification of o-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies

  摘要：

  An efficient synthesis of 2- or 4-iododibenzofurans through Cul-mediated sequential iodination/cycloetherification of two aromatic C-H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO2, CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C-H activation step is involved in cycloetherification.

  DOI：

  10.1021/ol302562a

文献信息

• Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of <i>o</i>-Arylphenols for the Preparation of Dibenzofurans
  作者：Jiaji Zhao、Yong Wang、Yimiao He、Lanying Liu、Qiang Zhu

  DOI：10.1021/ol203442a

  日期：2012.2.17

  A new process involving copper-catalyzed aerobic C(sp(2))-H activation, followed by cycloetherification, has been developed. This reaction serves as a direct method for the preparation of multisubstituted dibenzofurans starting with o-arylphenols. The presence of a strong para-electron-withdrawing group (e.g., NO2) on the phenol is essential for the success of the reaction.