9-chloro-5-methoxyphenanthridin-6(5H)-one | 1275595-54-4

• 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: 9-chloro-5-methoxyphenanthridin-6(5H)-one
• 英文别名: 9-Chloro-5-methoxyphenanthridin-6-one
• CAS: 1275595-54-4
• 化学式: C₁₄H₁₀ClNO₂
• 分子量: 259.692
• InChiKey: IDAYDCZIAGTOOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-chloro-N-methoxybenzamide 在 溶剂黄146 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 10.25h， 生成 9-chloro-5-methoxyphenanthridin-6(5H)-one
  参考文献：
  名称：

  Palladium-catalyzed cyclization of benzamides with arynes: application to the synthesis of phenaglydon and N-methylcrinasiadine

  摘要：

  在钯催化剂的存在下，N-甲基或甲氧基取代的苯甲酰胺与苯乙炔反应，生成三环的N-甲基或N-甲氧基取代的苯并三氮杂环酮。

  DOI：

  10.1039/c4cc05252h

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。
• Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C–H Amidation
  作者：Dongdong Liang、Wenbo Yu、Nam Nguyen、Jeffrey R. Deschamps、Gregory H. Imler、Yue Li、Alexander D. MacKerell、Chao Jiang、Fengtian Xue

  DOI：10.1021/acs.joc.7b00106

  日期：2017.4.7

  synthesis of phenanthridinones from N-methoxybenzamides using an oxidative C–H amidation reaction at room temperature in open air with modest to excellent yields. This method demonstrated unprecedented substrate scope. In particular, it solved the long-standing challenge in the synthesis of phenanthridinones with sterically demanding substitutions.

  我们报告了一种在室温下在露天条件下使用氧化的C–H酰胺化反应从N-甲氧基苯甲酰胺合成一种新型的菲啶酮的方法，该方法适度地提高了产率。这种方法证明了前所未有的基板范围。特别是，它解决了在立体上需要取代的菲啶酮类化合物合成中的长期挑战。
• One-Pot Formation of CC and CN Bonds through Palladium-Catalyzed Dual CH Activation: Synthesis of Phenanthridinones
  作者：Guan-Wu Wang、Ting-Ting Yuan、Dan-Dan Li

  DOI：10.1002/anie.201005874

  日期：2011.2.7

  Two cycles in one pot! The synthesis of biologically important phenanthridinones has been achieved by the one‐pot formation of CC and CN bonds through a palladium‐catalyzed dual CH activation, which involves four bond ruptures and two bond formations (see scheme). The conversion of phenanthridinones into natural product like derivatives further demonstrates the utility of this synthetic achievement

  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。
• 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。