1-(4-iodophenyl)-2-methyl-5-phenyl-1H-pyrrole | 26165-83-3

• 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-(4-iodophenyl)-2-methyl-5-phenyl-1H-pyrrole
• 英文别名: 1-(4-Iodophenyl)-2-methyl-5-phenylpyrrole
• CAS: 26165-83-3
• 化学式: C₁₇H₁₄IN
• 分子量: 359.209
• InChiKey: DCBHYAORBBIQMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  4-硝基碘苯 、 1-苯基-1,4-戊二酮 在 indium 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以84%的产率得到1-(4-iodophenyl)-2-methyl-5-phenyl-1H-pyrrole
  参考文献：
  名称：

  Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones

  摘要：

  One-pot reduction-triggered heterocyclizations of nitrobenzene derivatives with 1,4-diketones were investigated. In the presence of indium/AcOH in toluene at 80 degrees C, reaction of nitrobenzenes with 2,5-hexadione produced moderate to excellent yields (40-98%) of the corresponding pyrroles within 1.5-24 h depending on the substituents of the starting materials. Similarly, the reaction of nitrobenzenes with 1-phenyl-1,4-pantanedione in the presence of indium/AcOH in toluene at reflux afforded the corresponding pyrroles within 0.5-24 h with 60-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.113

文献信息

• Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation
  作者：Liudvikas Akelis、Jolanta Rousseau、Robertas Juskenas、Jelena Dodonova、Cyril Rousseau、Stéphane Menuel、Dominique Prevost、Sigitas Tumkevičius、Eric Monflier、Frédéric Hapiot

  DOI：10.1002/ejoc.201501223

  日期：2016.1

  A straightforward and solventless synthesis of pyrroles was developed by using mechanochemical activation and a biosourced organic acid as the catalyst. Relative to traditional Paal–Knorr methodologies, various N-substituted pyrroles were obtained in very short reaction times. By reaction with unreactive diketones, desymmetrized aliphatic and aromatic compounds were also synthesized.

  通过使用机械化学活化和生物来源的有机酸作为催化剂，开发了一种简单且无溶剂的吡咯合成方法。相对于传统的 Paal-Knorr 方法，可以在很短的反应时间内获得各种 N 取代的吡咯。通过与不活泼的二酮反应，还合成了去对称的脂肪族和芳香族化合物。