1-(2-(3,3-dimethylbut-1-ynyl)phenyl)-1H-pyrrole | 1311312-29-4

• 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-(3,3-dimethylbut-1-ynyl)phenyl)-1H-pyrrole
• 英文别名: 1-[2-(3,3-Dimethylbut-1-ynyl)phenyl]pyrrole
• CAS: 1311312-29-4
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: DLWRKGIUAVBMSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3,3-二甲基-1-丁炔 、 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-(3,3-dimethylbut-1-ynyl)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.