2-butyl-1-(toluene-4-sulfonyl)-5-p-tolyl-1H-pyrrole | 1159579-80-2

• 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-butyl-1-(toluene-4-sulfonyl)-5-p-tolyl-1H-pyrrole
• 英文别名: 2-Butyl-5-(4-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrole
• CAS: 1159579-80-2
• 化学式: C₂₂H₂₅NO₂S
• 分子量: 367.512
• InChiKey: AHCCUFUXAXUUCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-hex-1-yn-1-yl-1-(toluene-4-sulfonyl)-3-p-tolylaziridine 在 三苯基膦氯金 、 silver(I) 4-methylbenzenesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以98%的产率得到2-butyl-1-(toluene-4-sulfonyl)-5-p-tolyl-1H-pyrrole
  参考文献：
  名称：

  Counterion Effects in a Gold-Catalyzed Synthesis of Pyrroles from Alkynyl Aziridines

  摘要：

  Aryl-substituted N-tosyl alkynyl aziridines undergo a gold-catalyzed ring expansion to afford 2,5-substituted pyrrole products. Under certain conditions, a ring-expansion and rearrangement leads to 2,4-substituted pyrroles. The reaction pathway is determined by the counterion to the gold catalyst.

  DOI：

  10.1021/ol900609f

文献信息

• Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
  作者：Paul W Davies、Nicolas Martin、Neil Spencer

  DOI：10.3762/bjoc.7.96

  日期：——

  Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using (13)C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against

  进行同位素标记研究以探测在金催化的炔基氮丙啶环异构化成 2,4-二取代吡咯中所提出的 1,2-芳基位移。使用 (13) C 标记确定了预期骨骼重排产物的两种同位素，并导致了具有两种不同骨骼重排的修订机制。针对一系列 (13) C 和氘标记底物的反应，该机制建议已被合理化。
• An efficient and selective synthesis of 2,5-substituted pyrroles by gold-catalysed ring expansion of alkynyl aziridines
  作者：Paul W. Davies、Nicolas Martin

  DOI：10.1016/j.jorganchem.2010.08.040

  日期：2011.1

  A range of substituted alkynyl aziridines undergo a ring expansion to afford 2,5-substituted pyrroles under gold catalysis. While effective conditions can be generated from other gold sources, a combination of Ph3PAuCl and AgOTs generate a catalyst system that provides extremely clean cycloisomerisation reactions requiring minimal work-up and purification. (C) 2010 Elsevier B.V. All rights reserved.