ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate | 146537-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 1,4-bis(4-chlorophenyl)-2-methylpyrrole-3-carboxylate
• CAS: 146537-29-3
• 化学式: C₂₀H₁₇Cl₂NO₂
• 分子量: 374.266
• InChiKey: DZAAAIUUTLOPAK-UHFFFAOYSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  501.5±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以70%的产率得到1,4-Bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles

  摘要：

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.

  DOI：

  10.1016/0223-5234(92)90092-f
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 在 p-chlorobenzenamine hydrobromide 、 zinc(II) chloride 作用下， 以 乙醇 、 苯 为溶剂， 反应 24.0h， 生成 ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles

  摘要：

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.

  DOI：

  10.1016/0223-5234(92)90092-f

文献信息

• Recyclable, Graphite-Catalyzed, Four-Component Synthesis of Functionalized Pyrroles
  作者：K. N. Nandeesh、G. M. Raghavendra、C. N. Revanna、T. A. Jenifer Vijay、K. S. Rangappa、K. Mantelingu

  DOI：10.1080/00397911.2013.848368

  日期：2014.4.18

  Abstract A facile, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles is developed using graphite as a catalyst, but devoid of moisture-sensitive metal catalysts and corrosive acidic reagents. This method involves four-component coupling reactions of ethyl acetoacetate compound or diethyl acetylene dicarboxylate, amines, aromatic aldehydes, and nitromethane

  摘要 以石墨为催化剂，开发了一种简便、多组分的偶联策略，用于合成高度官能化的吡咯，但不使用对湿气敏感的金属催化剂和腐蚀性酸性试剂。该方法涉及乙酰乙酸乙酯化合物或乙炔二羧酸二乙酯、胺、芳香醛和硝基甲烷的四组分偶联反应，无需惰性气氛。这种方法可以通过一锅串联反应轻松获得高产率的高度取代的吡咯。与现有方法相比，该方法非常简单、直接且环保。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版本，获取以下免费补充资源：
• Triethanolammonium Acetate ([TEAH][OAc]) as a Recyclable Promoter and Medium for Green and Four-component Synthesis of Polyfunctionalized Pyrrole Derivatives
  作者：Behjat Pouramiri、Milad Daneshi、Fatemeh Seyedi、Najmeh Amirmahani

  DOI：10.2174/1570178617999200611150616

  日期：2021.3

  Multi-component synthesis of functionalized pyrrole derivatives was achieved via a fourcomponent condensation reaction of ethyl acetoacetate/ methyl acetoacetate, aromatic amines, nitromethane, and aromatic aldehydes using triethanolammonium acetate ([TEAH][OAc]) ionic liquid as a green solvent and catalyst. Easy access to highly substituted pyrroles, reusability of the catalyst, broad substrate scopes

  使用乙酸三乙醇铵（[TEAH] [OAc]）离子液体作为绿色溶剂和催化剂，通过乙酰乙酸乙酯/乙酰乙酸甲酯，芳香胺，硝基甲烷和芳香醛的四组分缩合反应，可以实现功能化吡咯衍生物的多组分合成。易于获得高度取代的吡咯，催化剂的可重复使用性，较宽的底物范围，无柱色谱法，反应时间短，产物收率高和无溶剂条件，使得该方案对环境友好且实用。
• Porretta; Biava; Fioravanti, Il Farmaco, 1995, vol. 50, # 9, p. 617 - 623
  作者：Porretta、Biava、Fioravanti、Fischetti、Boccia、Villa、Simonetti

  DOI：——

  日期：——
• Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles
  作者：GC Porretta、M Biava、R Fioravanti、M Fischetti、C Melino、F Venza、P Bolle、B Tita

  DOI：10.1016/0223-5234(92)90092-f

  日期：1992.10

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.