| 1200055-87-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• CAS: 1200055-87-3
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: IBEOQEJOZBQRBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.23
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 二乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以208 mg的产率得到6-硝基-2-苯基-4-喹啉醇
  参考文献：
  名称：

  Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source

  摘要：

  A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 degrees C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.

  DOI：

  10.1021/jo502400h
• 作为产物：
  描述：

  2-碘-4-硝基苯胺 、 苯乙炔 、 molybdenum hexacarbonyl 在 palladium diacetate 、 三乙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source

  摘要：

  A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 degrees C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.

  DOI：

  10.1021/jo502400h

文献信息

• Carbonylative Sonogashira Coupling in the Synthesis of Ynones: A Study of “Boomerang” Phenomena
  作者：Marie Genelot、Véronique Dufaud、Laurent Djakovitch

  DOI：10.1002/adsc.201300357

  日期：2013.9.16

  of several organophosphino‐palladium complexes immobilized on mesoporous silica during the palladium‐catalyzed synthesis of propynone by carbonylative Sonogashira coupling was studied, particularly concerning leaching/redeposition phenomena. The results demonstrated that this cross‐coupling reaction is catalyzed by soluble species. Furthermore, it is shown that the palladium leaching is not initiated

  研究了羰基Sonogashira偶联在钯催化的丙炔酮合成过程中固定在中孔二氧化硅上的几种有机膦-钯配合物的行为，特别是关于浸出/再沉积现象。结果表明，这种交叉偶联反应是由可溶性物质催化的。此外，已表明钯的浸出不是通过氧化加成步骤引发的，而是由接枝的配体进行的钯解配位引发的。尽管存在这种不协调性，回收后催化剂的性能仍然足够。另外，显示出与催化剂制备或反应程序相关的几个参数可减少浸出，从而使金属污染水平接近欧洲药品评估机构的建议。