1-[(E)-2-[1,1'-biphenyl]-4-ylethenyl]-1H-pyrrole | 1359619-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(E)-2-[1,1'-biphenyl]-4-ylethenyl]-1H-pyrrole
• 英文别名: 1-[(E)-2-(4-phenylphenyl)ethenyl]pyrrole
• CAS: 1359619-06-9
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: MBQIZVNHWYBXJK-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吡咯 、 4-乙炔联苯 在 potassium hydroxide semihydrate 作用下， 以 二甲基亚砜 为溶剂， 生成 1-[(Z)-2-[1,1'-biphenyl]-4-ylethenyl]-1H-pyrrole 、 1-[(E)-2-[1,1'-biphenyl]-4-ylethenyl]-1H-pyrrole
  参考文献：
  名称：

  Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

  摘要：

  A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 degrees C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole-phenylacetylene and 2-(2-thienyl)pyrrole-phenylacetylene, respectively). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.050

文献信息

• Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles
  作者：Marina Yu. Dvorko、Elena Yu. Schmidt、Tatyana E. Glotova、Dmitrii A. Shabalin、Igor' A. Ushakov、Vladimir B. Kobychev、Konstantin B. Petrushenko、Al'bina I. Mikhaleva、Boris A. Trofimov

  DOI：10.1016/j.tet.2011.12.050

  日期：2012.2

  A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 degrees C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole-phenylacetylene and 2-(2-thienyl)pyrrole-phenylacetylene, respectively). (C) 2011 Elsevier Ltd. All rights reserved.