3-(p-tolyl)-1-tosyl-1H-pyrrole | 1584705-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(p-tolyl)-1-tosyl-1H-pyrrole
• 英文别名: 3-(4-Methylphenyl)-1-(4-methylphenyl)sulfonylpyrrole；3-(4-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrole
• CAS: 1584705-39-4
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: WIHBGIGFFBYAND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole 、 乙烯基乙醚 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以76%的产率得到3-(p-tolyl)-1-tosyl-1H-pyrrole
  参考文献：
  名称：

  Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles

  摘要：

  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.

  DOI：

  10.1021/jo501043h

文献信息

• Synthesis of Pyrroles from Terminal Alkynes, <i>N</i>-Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1-Sulfonyl-1,2,3-triazoles
  作者：Cheol-Eui Kim、Sangjune Park、Dahan Eom、Boram Seo、Phil Ho Lee

  DOI：10.1021/ol500718s

  日期：2014.4.4

  A method for synthesis of substituted pyrroles has been developed. 1-Sulfonyl-1,2,3-triazoles generated from terminal alkynes gave alpha-imino rhodium carbene complexes, which when reacted with alkenyl alkyl ethers afforded substituted pyrroles. The method can be efficiently applied to a one-pot sequential reaction starting from terminal alkynes.
• Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles
  作者：Shanmugam Rajasekar、Pazhamalai Anbarasan

  DOI：10.1021/jo501043h

  日期：2014.9.5

  Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent.