2,5-diphenyl-1-(toluene-4-sulfonyl)-1H-pyrrole | 910896-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-diphenyl-1-(toluene-4-sulfonyl)-1H-pyrrole
• 英文别名: 2,5-diphenyl-1-tosyl-1H-pyrrole；1-(4-Methylphenyl)sulfonyl-2,5-diphenylpyrrole；1-(4-methylphenyl)sulfonyl-2,5-diphenylpyrrole
• CAS: 910896-11-6
• 化学式: C₂₃H₁₉NO₂S
• 分子量: 373.475
• InChiKey: GQVXILPBYXFNHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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-phenyl-3-phenylethynyl-1-(toluene-4-sulfonyl)aziridine 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 3.0h， 以98%的产率得到2,5-diphenyl-1-(toluene-4-sulfonyl)-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

• A facile and regioselective synthesis of 2,5-disubstituted pyrroles via gold-catalyzed cycloisomerization of acetylenylaziridines
  作者：Dong-Dong Chen、Xue-Long Hou、Li-Xin Dai

  DOI：10.1016/j.tetlet.2009.05.091

  日期：2009.12

  Gold-catalyzed cycloisomerization reaction of acetylenylaziridines provides 2,5-disubstituted pyrroles in high yields. The presence of protic species accelerates the reaction rate and improves the yields of pyrrole products.

  乙炔基氮丙啶的金催化的环异构化反应以高收率提供了2,5-二取代的吡咯。质子物种的存在加快了反应速度并提高了吡咯产物的产率。
• Revisiting the Influence of Silver in Cationic Gold Catalysis: A Practical Guide
  作者：Zhichao Lu、Junbin Han、Gerald B. Hammond、Bo Xu

  DOI：10.1021/acs.orglett.5b02224

  日期：2015.9.18

  salt to generate cationic gold from a gold catalyst precursor such as L–Au–Cl almost always has adverse effects on the reactivity of the cationic gold catalyst. A preformed L–Au+X– complex, generated by sonication followed by centrifugation, increases the reactivity in a gold catalyzed reaction. The adverse silver effect might be caused by the interaction of silver salts with gold intermediates.

  过量的银盐会从金催化剂前体（例如L–Au–Cl）生成阳离子金，几乎总是对阳离子金催化剂的反应性产生不利影响。通过超声然后离心分离生成的预先形成的L–Au + X –络合物可提高金催化反应的反应性。银的不利影响可能是由银盐与金中间体的相互作用引起的。
• 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.