2-methyl-1-(naphthalene-1-yl)-5-phenyl-1H-pyrrole | 313483-14-6

• 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-methyl-1-(naphthalene-1-yl)-5-phenyl-1H-pyrrole
• 英文别名: 1-(naphthalen-1-yl)-2-methyl-5-phenyl-1H-pyrrole；2-methyl-1-[1]naphthyl-5-phenyl-pyrrole；2-Methyl-1-[1]naphthyl-5-phenyl-pyrrol；2-Methyl-1-naphthalen-1-yl-5-phenylpyrrole
• CAS: 313483-14-6
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: SQSZCWZCKCQOHW-UHFFFAOYSA-N

物化性质

• 沸点：
  469.9±14.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 2-methyl-1-(naphthalene-1-yl)-5-phenyl-1H-pyrrole 在 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以30%的产率得到1-Methyl-4-[[2-methyl-1-(1-naphthyl)-5-phenyl-pyrrol-3-yl]methyl]piperazine
  参考文献：
  名称：

  Antimycobacterial compounds. New pyrrole derivatives of BM212

  摘要：

  We have identified BM212 as a lead compound among a series of pyrrole derivatives with good in vitro activity against mycobacteria and candidae. First studies led us to synthesize some pyrrole compounds in which the thiomorpholine fragment was present. Some compounds revealed very active and these findings prompted us to prepare new pyrrole derivatives 2-15 in the hope of increasing the activity. The microbiological data showed interesting in vitro activity against Mycobacterium tuberculosis and atypical mycobacteria. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.037
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2-methyl-1-(naphthalene-1-yl)-5-phenyl-1H-pyrrole
  参考文献：
  名称：

  Lederer; Paal, Chemische Berichte, 1885, vol. 18, p. 2598

  摘要：

  DOI：

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。
• Indium-mediated one-pot pyrrole synthesis from nitrobenzenes and 1,4-diketones
  作者：Hyunseung Lee、Byeong Hyo Kim

  DOI：10.1016/j.tet.2013.05.113

  日期：2013.8

  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.