2-cyclohex-1-en-1-yl-5-phenyl-1H-pyrrole | 1132645-54-5

• 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-cyclohex-1-en-1-yl-5-phenyl-1H-pyrrole
• 英文别名: 2-(cyclohexen-1-yl)-5-phenyl-1H-pyrrole
• CAS: 1132645-54-5
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: IXEFVFRSMFQKQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-cyclohex-1-en-1-yl-5-phenyl-1H-pyrrole 在 zinc(II) chloride 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 105.0 ℃ 、500.01 kPa 条件下， 反应 0.5h， 以67%的产率得到2-cyclohexyl-5-phenyl-1H-pyrrole
  参考文献：
  名称：

  Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides

  摘要：

  Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high to moderate yields (91-41%). Both conventional and microwave protocols furnished comparable results. A structure of 2-(4-fluorophenyl)-5-(4-methyl-phenyl)-1H-pyrrole was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.094
• 作为产物：
  描述：

  4-cyclohex-1-en-1-yl-1-phenylbut-3-yn-1-yl azide 在 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 130.0 ℃ 、200.0 kPa 条件下， 反应 0.67h， 以64%的产率得到2-cyclohex-1-en-1-yl-5-phenyl-1H-pyrrole
  参考文献：
  名称：

  Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides

  摘要：

  Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high to moderate yields (91-41%). Both conventional and microwave protocols furnished comparable results. A structure of 2-(4-fluorophenyl)-5-(4-methyl-phenyl)-1H-pyrrole was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.094

文献信息

• Microwave-assisted zinc chloride-catalyzed synthesis of substituted pyrroles from homopropargyl azides
  作者：Przemysław Wyrębek、Adam Sniady、Nicholas Bewick、Yan Li、Agnieszka Mikus、Kraig A. Wheeler、Roman Dembinski

  DOI：10.1016/j.tet.2008.11.094

  日期：2009.2

  Ligand-free 5-endo-dig cyclization of 1,4- and 1,2,4-substituted but-3-yn-1-yl (homopropargyl) azides in the presence of zinc chloride (usually 20 mol %) in dichloroethane at elevated temperature provides 2,5-di- and 2,3,5-trisubstituted pyrroles in high to moderate yields (91-41%). Both conventional and microwave protocols furnished comparable results. A structure of 2-(4-fluorophenyl)-5-(4-methyl-phenyl)-1H-pyrrole was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.