7,9-dihydroxyfluoranthene | 144468-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,9-dihydroxyfluoranthene
• 英文别名: 7,9-Fluoranthenediol；fluoranthene-7,9-diol
• CAS: 144468-23-5
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: MZNWWLNVPGIJEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硼酸三丁酯 、 KTMP 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 以37%的产率得到8-hydroxyfluoranthene
  参考文献：
  名称：

  Metal arene complexes in organic synthesis. Hydroxylation, trimethylsilylation, and carbethoxylation of some polycyclic aromatic hydrocarbons utilizing .eta.6-arene-chromium tricarbonyl complexes

  摘要：

  The deprotonation of polycyclic aromatic hydrocarbon (PAH) chromium tricarbonyl complexes (PAH = naphthalene, anthracene, phenanthrene, pyrene, fluoranthene) using an in situ technique where the PAH complex, the base (LiTMP or LDA), and the electrophile (trialkyl borate, trimethylsilyl chloride, or ethyl chloroformate) were placed in solution simultaneously resulted in hydroxylation, trimethylsilylation, or carbethoxylation of the PAH after oxidative workup where the regiochemistry was controlled by steric factors. As a result, substitution at positions of the PAHs not readily available by electrophilic substitution were obtained in some cases. Conditions minimizing isomer mixtures and factors affecting the regiochemistry and the scope of the reaction sequence were examined.

  DOI：

  10.1021/jo00050a023

文献信息

• Metal arene complexes in organic synthesis. Hydroxylation, trimethylsilylation, and carbethoxylation of some polycyclic aromatic hydrocarbons utilizing .eta.6-arene-chromium tricarbonyl complexes
  作者：James A. Morley、Neil F. Woolsey

  DOI：10.1021/jo00050a023

  日期：1992.11

  The deprotonation of polycyclic aromatic hydrocarbon (PAH) chromium tricarbonyl complexes (PAH = naphthalene, anthracene, phenanthrene, pyrene, fluoranthene) using an in situ technique where the PAH complex, the base (LiTMP or LDA), and the electrophile (trialkyl borate, trimethylsilyl chloride, or ethyl chloroformate) were placed in solution simultaneously resulted in hydroxylation, trimethylsilylation, or carbethoxylation of the PAH after oxidative workup where the regiochemistry was controlled by steric factors. As a result, substitution at positions of the PAHs not readily available by electrophilic substitution were obtained in some cases. Conditions minimizing isomer mixtures and factors affecting the regiochemistry and the scope of the reaction sequence were examined.