9-(tert-butyl)-5-methoxyphenanthridin-6(5H)-one | 1435477-65-8

• 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: 9-(tert-butyl)-5-methoxyphenanthridin-6(5H)-one
• 英文别名: 9-Tert-butyl-5-methoxyphenanthridin-6-one
• CAS: 1435477-65-8
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: AUJVEPGNYJYLFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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-(tert-butyl)-N-methoxybenzamide 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 四丁基溴化铵 、 copper diacetate 、 palladium diacetate 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 15.0h， 以92%的产率得到9-(tert-butyl)-5-methoxyphenanthridin-6(5H)-one
  参考文献：
  名称：

  Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C–H/N–H Activation for the Synthesis of N-Heterocycles

  摘要：

  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.

  DOI：

  10.1021/ol5025426

文献信息

• 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。
• 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.