1-(2-((3-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole | 1311312-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-((3-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole
• 英文别名: 1-[2-[2-(3-Methoxyphenyl)ethynyl]phenyl]pyrrole
• CAS: 1311312-25-0
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: JKFQSXBEBKFIGX-UHFFFAOYSA-N

物化性质

• 沸点：
  450.4±30.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-((3-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以81%的产率得到5-iodo-4-(3-methoxyphenyl)pyrrolo[1,2-a]quinoline
  参考文献：
  名称：

  Synthesis of 5-Iodopyrrolo[1,2-a]quinolines and Indolo[1,2-a]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-endo-dig Ring Closure

  摘要：

  The endo-cyclic ring closure of 1-(2-(substituted ethynyl)pheny1)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I-2) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.

  DOI：

  10.1021/jo200638k
• 作为产物：
  描述：

  3-乙炔基苯甲醚 、 1-(2-碘苯基)吡咯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 1-(2-((3-methoxyphenyl)ethynyl)phenyl)-1H-pyrrole
  参考文献：
  名称：

  Synthesis of 5-Iodopyrrolo[1,2-a]quinolines and Indolo[1,2-a]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-endo-dig Ring Closure

  摘要：

  The endo-cyclic ring closure of 1-(2-(substituted ethynyl)pheny1)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I-2) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.

  DOI：

  10.1021/jo200638k

文献信息

• Synthesis of 5-Iodopyrrolo[1,2-<i>a</i>]quinolines and Indolo[1,2-<i>a</i>]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-<i>endo</i>-<i>dig</i> Ring Closure
  作者：Akhilesh Kumar Verma、Satya Prakash Shukla、Jaspal Singh、Vineeta Rustagi

  DOI：10.1021/jo200638k

  日期：2011.7.15

  The endo-cyclic ring closure of 1-(2-(substituted ethynyl)pheny1)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I-2) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.