5-methoxy-9-nitrophenanthridin-6(5H)-one | 1275595-58-8

• 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-nitrophenanthridin-6(5H)-one
• 英文别名: 5-Methoxy-9-nitrophenanthridin-6-one
• CAS: 1275595-58-8
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: NQQWVBBIGKZPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 silver(l) oxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 72.0h， 生成 5-methoxy-9-nitrophenanthridin-6(5H)-one
  参考文献：
  名称：

  的C一锅形成的？C和C ？N键通过钯催化双Ç ？H活化：菲啶酮类化合物的合成

  摘要：

  一锅两个循环！的生物学上重要的phenanthridinones合成已经由一锅煮形成C ++实现 C和C  N键通过钯催化的双Ç  ħ活化，这涉及四个键断裂和两个键的形成（参见方案）。菲啶酮向天然产物如衍生物的转化进一步证明了该合成成果的实用性。

  DOI：

  10.1002/anie.201005874

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。
• A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides
  作者：Dengke Li、Ning Xu、Yicheng Zhang、Lei Wang

  DOI：10.1039/c4cc06457g

  日期：——

  A Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. Anilides afforded ortho-arylation products, and N-methoxyarylamides gave phenanthridinones.

  通过Pd催化的酰过氧化物与酰胺的脱羧ortho-芳基化反应被开发出来。苯胺酰胺产生ortho-芳基化产物，N-甲氧基芳胺酰胺产生菲啰啉酮。
• 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.
• Annulation of Benzamides with Arynes Using Palladium with Photoredox Dual Catalysis
  作者：Jie Zhao、Hongji Li、Pinhua Li、Lei Wang

  DOI：10.1021/acs.joc.9b00893

  日期：2019.7.19

  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.