N-{5-ethynyl-1-(methylsulfonyl)pyrrolo[3,2-b]pyridin-6-yl}methanesulfonamide | 1159200-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: N-{5-ethynyl-1-(methylsulfonyl)pyrrolo[3,2-b]pyridin-6-yl}methanesulfonamide
• 英文别名: N-(5-ethynyl-1-methylsulfonylpyrrolo[3,2-b]pyridin-6-yl)methanesulfonamide
• CAS: 1159200-41-5
• 化学式: C₁₁H₁₁N₃O₄S₂
• 分子量: 313.358
• InChiKey: UQEJNPCUFIVERF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-{5-ethynyl-1-(methylsulfonyl)pyrrolo[3,2-b]pyridin-6-yl}methanesulfonamide 、 二乙胺 以 甲苯 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.33h， 以26 mg的产率得到2-[(N,N-diethylamino)methyl]-1,7-bis(methylsulfonyl)dipyrrolo[3,2-b:2',3'-e]pyridine
  参考文献：
  名称：

  Efficient Synthesis of Aminomethylated Pyrroloindoles and Dipyrrolopyridines via Controlled Copper-Catalyzed Domino Multicomponent Coupling and Bis-cyclization

  摘要：

  Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.

  DOI：

  10.1021/jo900681p
• 作为产物：
  描述：

  N,N'-(2,6-diethynylpyridine-3,5-diyl)dimethanesulfonamide 在 copper(l) iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以81%的产率得到N-{5-ethynyl-1-(methylsulfonyl)pyrrolo[3,2-b]pyridin-6-yl}methanesulfonamide
  参考文献：
  名称：

  Efficient Synthesis of Aminomethylated Pyrroloindoles and Dipyrrolopyridines via Controlled Copper-Catalyzed Domino Multicomponent Coupling and Bis-cyclization

  摘要：

  Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.

  DOI：

  10.1021/jo900681p

文献信息

• Efficient Synthesis of Aminomethylated Pyrroloindoles and Dipyrrolopyridines via Controlled Copper-Catalyzed Domino Multicomponent Coupling and Bis-cyclization
  作者：Yamato Suzuki、Yusuke Ohta、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo900681p

  日期：2009.6.5

  Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.