2-methyl-4-phenyl-1-tosyl-1H-pyrrole | 1006062-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-methyl-4-phenyl-1-tosyl-1H-pyrrole
• 英文别名: 2-Methyl-1-(4-methylphenyl)sulfonyl-4-phenylpyrrole；2-methyl-1-(4-methylphenyl)sulfonyl-4-phenylpyrrole
• CAS: 1006062-36-7
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: RUKAJGRSEAFMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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

• 作为反应物：
  描述：

  2-methyl-4-phenyl-1-tosyl-1H-pyrrole 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以81%的产率得到2-methyl-4-phenylpyrrole
  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
• 作为产物：
  描述：

  N-(1-甲氧基-2-苯基烯丙基)-N-(1-甲基烯丙基)-4-甲基苯磺酰胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 三氟乙酸 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 24.0h， 以54%的产率得到2-methyl-4-phenyl-1-tosyl-1H-pyrrole
  参考文献：
  名称：

  灵活的基于易位的呋喃和吡咯的方法

  摘要：

  通过明智地使用闭环复分解/芳构化策略，已在短时间内合成了一系列功能不同的呋喃和吡咯。描述了两种对比方法，一种是利用钯催化的烯丙基醇和磺酰胺的结合，另一种是利用钛介导的均烯丙基酯的甲基化。通过传统方法难以安装的许多组已成功合并。

  DOI：

  10.1016/j.tet.2007.09.087

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.
• Synthesis of 2,3-Dihydropyrroles by Rhodium(II)-Catalyzed Transannulation of <i>N</i>-Sulfonyl-1,2,3-triazoles: Diversity Generation by One-Pot Methodologies
  作者：Caterina Permingeat Squizatto、Maira A. Bianchini、Carina M.L. Delpiccolo

  DOI：10.1021/acs.joc.3c01337

  日期：2023.12.1
• 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.
• Flexible metathesis-based approaches to highly functionalised furans and pyrroles
  作者：Timothy J. Donohoe、Neil M. Kershaw、Allan J. Orr、Katherine M.P. Wheelhouse (nee Gosby)、Lisa P. Fishlock、Adam R. Lacy、Matilda Bingham、Panayiotis A. Procopiou

  DOI：10.1016/j.tet.2007.09.087

  日期：2008.1.28

  have been synthesised in short order by the judicious use of a ring-closing metathesis/aromatisation strategy. Two contrasting approaches are described exploiting a palladium-catalysed union of allylic alcohols and sulfonamides in one case, and a titanium mediated methylenation of homoallylic esters in another. A number of groups that are difficult to install via traditional methods were incorporated

  通过明智地使用闭环复分解/芳构化策略，已在短时间内合成了一系列功能不同的呋喃和吡咯。描述了两种对比方法，一种是利用钯催化的烯丙基醇和磺酰胺的结合，另一种是利用钛介导的均烯丙基酯的甲基化。通过传统方法难以安装的许多组已成功合并。