1-(2-溴-4-氟苯基)-1H-吡咯 | 383137-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(2-溴-4-氟苯基)-1H-吡咯
• 英文名称: 1-(2-bromo-4-fluoro-phenyl)-1H-pyrrole
• 英文别名: 1-(2-Bromo-4-fluorophenyl)-1H-pyrrole；1-(2-bromo-4-fluorophenyl)pyrrole
• CAS: 383137-41-5
• 化学式: C₁₀H₇BrFN
• 分子量: 240.075
• InChiKey: XPKKSELXAGBMIA-UHFFFAOYSA-N

物化性质

• 沸点：
  284.4±30.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-溴-4-氟苯基)-1H-吡咯 、 2,5-降冰片二烯 在 palladium diacetate 、 三苯基膦 caesium carbonate 作用下， 以 甲苯 为溶剂， 以86%的产率得到7-Fluoropyrrolo[1,2-a]quinoline
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Aryl Heterocycles with Strained Alkenes

  摘要：

  An annulation reaction proceeding by the intermolecular addition of an arylpalladium(II) halide across a strained alkene, followed by an intramolecular C-H functionalization of a pendant heterocycle is described. A variety of polycyclic heterocycles have been prepared from readily accessible haloaryl heterocycles by annulation with a range of strained alkene partners.

  DOI：

  10.1021/ol070475w
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 2-溴-4-氟苯胺 在 溶剂黄146 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 以98%的产率得到1-(2-溴-4-氟苯基)-1H-吡咯
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Aryl Heterocycles with Strained Alkenes

  摘要：

  An annulation reaction proceeding by the intermolecular addition of an arylpalladium(II) halide across a strained alkene, followed by an intramolecular C-H functionalization of a pendant heterocycle is described. A variety of polycyclic heterocycles have been prepared from readily accessible haloaryl heterocycles by annulation with a range of strained alkene partners.

  DOI：

  10.1021/ol070475w

文献信息

• Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp²)–H Bond Functionalization
  作者：Shuai Xu、Ri Chen、Zihao Fu、Qi Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1021/acscatal.6b03562

  日期：2017.3.3

  A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C–C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source

  已经开发出了一种高效且操作简单的钯催化的正[4 +1]环化反应。该反应的特征是在羧基中心上形成两个不同的C–C键。它代表了一种简便的方法，用于合成多种多环芳烃（PAH）和1 H-茚，并以易于获得的（三甲基甲硅烷基）重氮甲烷作为卡宾源。金属卡宾迁移插入和C（sp 2）–H键活化被提议为该转变的关键步骤。该反应进一步证明了与各种过渡金属催化的转化结合的基于卡宾的偶联的多功能性。
• Palladium-Catalyzed Annulation of Aryl Heterocycles with Strained Alkenes
  作者：David G. Hulcoop、Mark Lautens

  DOI：10.1021/ol070475w

  日期：2007.4.1

  An annulation reaction proceeding by the intermolecular addition of an arylpalladium(II) halide across a strained alkene, followed by an intramolecular C-H functionalization of a pendant heterocycle is described. A variety of polycyclic heterocycles have been prepared from readily accessible haloaryl heterocycles by annulation with a range of strained alkene partners.