5-methoxy-9-(trifluoromethyl)phenanthridin-6(5H)-one | 1435477-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methoxy-9-(trifluoromethyl)phenanthridin-6(5H)-one
• 英文别名: 5-Methoxy-9-(trifluoromethyl)phenanthridin-6-one
• CAS: 1435477-69-2
• 化学式: C₁₅H₁₀F₃NO₂
• 分子量: 293.245
• InChiKey: XPIYZNMHASXXKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-methoxy-4-(trifluoromethyl)benzamide 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 C₂₀H₈Br₄O₄^(2-)*2Na⁽¹⁺⁾ 、 氧气 、 palladium diacetate 、 cesium fluoride 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以72%的产率得到5-methoxy-9-(trifluoromethyl)phenanthridin-6(5H)-one
  参考文献：
  名称：

  Annulation of Benzamides with Arynes Using Palladium with Photoredox Dual Catalysis

  摘要：

  Efficient annulation of benzamides with arynes using palladium and photoredox dual catalysis under an oxygen atmosphere is disclosed, which circumvents the use of external toxic metal oxidant and proceeds readily via aryne insertion at room temperature to construct the phenanthridinone backbone.

  DOI：

  10.1021/acs.joc.9b00893

文献信息

• Synthesis of Phenanthridinones from<i>N</i>-Methoxybenzamides and Aryltriethoxysilanes through Rh^III-Catalyzed CH and NH Bond Activation
  作者：Natarajan Senthilkumar、Kanniyappan Parthasarathy、Parthasarathy Gandeepan、Chien-Hong Cheng

  DOI：10.1002/asia.201300356

  日期：2013.9

  An efficient method for the one‐pot synthesis of substituted phenanthridinone derivatives from N‐methoxybenzamides and aryltriethoxysilanes through rhodium‐catalyzed dual CH bond activation and annulation reactions is described. A double‐cycle mechanism is proposed to account for this catalytic reaction. In addition, isotope‐labeling studies were performed to understand the intimate mechanism of the

  用于一锅合成选自于取代的菲啶衍生物的有效方法Ñ通过铑催化的双Ç-methoxybenzamides和aryltriethoxysilanes 描述H键活化和环反应。提出了双循环机制来解释该催化反应。另外，进行了同位素标记研究以了解反应的内在机理。
• Rhodium(III)-Catalyzed Oxidative CH Coupling of<i>N</i>-Methoxybenzamides with Aryl Boronic Acids: One-Pot Synthesis of Phenanthridinones
  作者：Jaganathan Karthikeyan、Radhakrishnan Haridharan、Chien-Hong Cheng

  DOI：10.1002/anie.201206890

  日期：2012.12.3

  General solution: An efficient rhodium‐catalyzed dual CH bond activation and cyclization of N‐methoxybenzamides 1 with aryl boronic acids 2 (see scheme; Cp*=Me5C5) provides a straightforward and general approach to the phenanthridinone structure, which occurs widely in natural products and drugs. Highly regioselective CC and CN bond formation under mild conditions afforded a wide range of substituted

  通用解决方案：有效的铑催化的双CH键活化和N-甲氧基苯甲酰胺1与芳基硼酸2的环化（参见方案； Cp * = Me 5 C 5）提供了一种直接而通用的方法用于菲咯啶酮结构，广泛存在于天然产物和药物中。在温和条件下形成高度区域选择性的CC和CN键可提供广泛的取代菲啶酮3。
• Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C–H/N–H Activation for the Synthesis of <i>N</i>-Heterocycles
  作者：Xianglong Peng、Weiguo Wang、Chao Jiang、Di Sun、Zhenghu Xu、Chen-Ho Tung

  DOI：10.1021/ol5025426

  日期：2014.10.17

  Strained alkynes include arynes and cyclooctynes reacted with N-methoxyamides through palladium-catalyzed C-H/N-H activation for the first time. A variety of important N-heterocycles such as phenanthridinones and isoquinolones were constructed in one step with high efficiency.