1-(3-(furan-2-yl)-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethanone | 1251914-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-(3-(furan-2-yl)-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethanone
• 英文别名: 1-[2-(Furan-2-yl)-5,6-dihydrobenzo[b][1]benzazepin-11-yl]ethanone；1-[2-(furan-2-yl)-5,6-dihydrobenzo[b][1]benzazepin-11-yl]ethanone
• CAS: 1251914-05-2
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: AYSLZTMJSDNHKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-呋喃硼酸 、 3-氯-5-乙酰基-10,11-二氢-5H-二苯并[b,f]氮杂卓 在 potassium phosphate 、 XPhos Pd G2 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以99%的产率得到1-(3-(furan-2-yl)-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethanone
  参考文献：
  名称：

  A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

  摘要：

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.

  DOI：

  10.1021/ja1073799

文献信息

• A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
  作者：Tom Kinzel、Yong Zhang、Stephen L. Buchwald

  DOI：10.1021/ja1073799

  日期：2010.10.13

  Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 degrees C in short reaction times to give the desired products in excellent yields.