5-methoxy-1,N,N-trimethylindole-3-carboxamide | 1088708-64-8

• 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: 5-methoxy-1,N,N-trimethylindole-3-carboxamide
• 英文别名: 5-methoxy-N,N,1-trimethylindole-3-carboxamide
• CAS: 1088708-64-8
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: YDQAXKVJKCBVSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  5-methoxy-1,N,N-trimethylindole-3-carboxamide 、 丙二酸,二(3-苯基-2-炔丙基)-,二乙基酯 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以95%的产率得到diethyl 8-methoxy-5-methyl-4,10-diphenyl-3,5-dihydrocyclopen ta[b]carbazole-2,2(1H)-dicarboxylate
  参考文献：
  名称：

  RhIII级联的CH / CC键断裂和环化反应催化的环戊[b]咔唑合成：使用酰胺作为无痕导向基团。

  摘要：

  已开发出铑催化的级联CH / CC裂解和3-酰胺取代的吲哚与二炔的环化反应，以构建环戊[b]咔唑。在该方案中已公开了一种策略酰胺，它作为一种新型的无痕导向基团，以及通过Friedel-Crafts-retro反应的CC键裂解。该方法显示出广泛的底物范围并耐受各种官能团，从而以良好或高收率提供了咔唑衍生物。

  DOI：

  10.1021/acs.orglett.9b03969
• 作为产物：
  描述：

  5-methoxy-1,N,N-trimethyl-2,3-dihydro-1H-indole-3-carboxamide 在 air 作用下， 生成 5-methoxy-1,N,N-trimethylindole-3-carboxamide
  参考文献：
  名称：

  Intramolecular Pd(0)-Catalyzed Reactions of β-(2-Iodoanilino) Carboxamides: Enolate Arylation and Nucleophilic Substitution at the Carboxamide Group

  摘要：

  Two different reaction pathways, the enolate arylation and the acylation of the aryl halide, can be promoted by a Pd(0) catalyst starting from beta-(2-iodoanilino) carboxamides. The intramolecular acylation of beta-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a sigma-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.

  DOI：

  10.1021/jo8020715

文献信息

• Rh^III-Catalyzed Synthesis of Cyclopenta[<i>b</i>]carbazoles via Cascade C–H/C–C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group
  作者：Yanwei Wang、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.9b03969

  日期：2020.1.3

  Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[b]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional

  已开发出铑催化的级联CH / CC裂解和3-酰胺取代的吲哚与二炔的环化反应，以构建环戊[b]咔唑。在该方案中已公开了一种策略酰胺，它作为一种新型的无痕导向基团，以及通过Friedel-Crafts-retro反应的CC键裂解。该方法显示出广泛的底物范围并耐受各种官能团，从而以良好或高收率提供了咔唑衍生物。
• Intramolecular Pd(0)-Catalyzed Reactions of β-(2-Iodoanilino) Carboxamides: Enolate Arylation and Nucleophilic Substitution at the Carboxamide Group
  作者：Daniel Solé、Olga Serrano

  DOI：10.1021/jo8020715

  日期：2008.12.5

  Two different reaction pathways, the enolate arylation and the acylation of the aryl halide, can be promoted by a Pd(0) catalyst starting from beta-(2-iodoanilino) carboxamides. The intramolecular acylation of beta-(2-iodoanilino) carboxamides reported here is the first example of a nucleophilic attack of a sigma-arylpalladium species at the carboxamide group, a framework that is usually inert toward organopalladium reagents.