N,N-diethyl-2-(4-methoxyphenyl)-1H-indole-1-carboxamide | 1039557-32-8

• 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-diethyl-2-(4-methoxyphenyl)-1H-indole-1-carboxamide
• 英文别名: N,N-diethyl-2-(4-methoxyphenyl)indole-1-carboxamide
• CAS: 1039557-32-8
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: PKPUGIYYLMVIIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-(4-methoxyphenyl)-1H-indole-1-carboxamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到N,N-diethyl-2-(1H-indol-2-yl)-5-methoxybenzamide
  参考文献：
  名称：

  Anionic Indole N-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles

  摘要：

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).

  DOI：

  10.1021/ol800307g
• 作为产物：
  描述：

  、 4-碘苯甲醚 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以1.30 g的产率得到N,N-diethyl-2-(4-methoxyphenyl)-1H-indole-1-carboxamide
  参考文献：
  名称：

  Anionic Indole N-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles

  摘要：

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).

  DOI：

  10.1021/ol800307g

文献信息

• Anionic Indole <i>N</i>-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[<i>a</i>]carbazoles and Indeno[1,2-<i>b</i>]indoles
  作者：Zhongdong Zhao、Ashley Jaworski、Isabel Piel、Victor Snieckus

  DOI：10.1021/ol800307g

  日期：2008.7.3

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).