N,N,3-trimethyl-2-phenyl-1H-indole-1-carboxamide | 1414351-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N,3-trimethyl-2-phenyl-1H-indole-1-carboxamide
• 英文别名: N,N,3-trimethyl-2-phenylindole-1-carboxamide
• CAS: 1414351-26-0
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: WQYGNEHRZYZWCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  非草隆 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 copper diacetate 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 36.0h， 生成 N,N,3-trimethyl-2-phenyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives

  摘要：

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.

  DOI：

  10.1021/ja310153v

文献信息

• Indole Synthesis via Cobalt(III)-Catalyzed Oxidative Coupling of <i>N</i>-Arylureas and Internal Alkynes
  作者：Zhuo-Zhuo Zhang、Bin Liu、Jing-Wen Xu、Sheng-Yi Yan、Bing-Feng Shi

  DOI：10.1021/acs.orglett.6b00494

  日期：2016.4.15

  A mild Co(III)-catalyzed oxidative annulation of N-arylureas and internal alkynes has been developed. The use of less electrophilic ureas other than acetamides as directing groups is crucial for the reaction. A broad range of synthetically useful functional groups are compatible with this reaction, thus providing a new opportunity for the synthesis of diverse indoles.

  已经开发了温和的Co（III）催化的N-芳基脲和内部炔烃的氧化环化反应。对于反应而言，使用至关重要的是使用乙酰胺以外的亲电性较低的尿素作为导向基团。广泛的合成有用的官能团与该反应相容，因此为合成各种吲哚提供了新的机会。
• Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives
  作者：Honggen Wang、Christoph Grohmann、Corinna Nimphius、Frank Glorius

  DOI：10.1021/ja310153v

  日期：2012.12.5

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.