1-methyl-2,5-bis(4-nitrophenyl)pyrrole | 137596-50-0

• 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-methyl-2,5-bis(4-nitrophenyl)pyrrole
• 英文别名: 2,5-bis(4-nitrophenyl)-1-methylpyrrole；N-methyl-2,5-di(4-nitrophenyl)pyrrole
• CAS: 137596-50-0
• 化学式: C₁₇H₁₃N₃O₄
• 分子量: 323.308
• InChiKey: LPXTZWRQCOVWIN-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C(Solv: acetic acid (64-19-7); acetone (67-64-1))
• 沸点：
  500.4±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 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：
  96.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-2,5-bis(4-nitrophenyl)pyrrole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 21.0h， 生成
  参考文献：
  名称：

  SYNTHESIS OF DICATIONIC 2,5-DIARYLPYRROLES

  摘要：

  DOI：

  10.1515/hc.2004.10.6.423
• 作为产物：
  描述：

  1,4-双(4-硝基苯基)丁烷-1,4-二酮 、 甲胺 在 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 48.0h， 以85%的产率得到1-methyl-2,5-bis(4-nitrophenyl)pyrrole
  参考文献：
  名称：

  Intermediates in the Paal-Knorr synthesis of pyrroles

  摘要：

  The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored. In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m). This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step. The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:03:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.

  DOI：

  10.1021/jo00024a040

文献信息

• Synthesis of 2,5-Diarylpyrroles by Ligand-Free Palladium-Catalyzed CH Activation of Pyrroles in Ionic Liquids
  作者：Peter Ehlers、Andranik Petrosyan、Jens Baumgard、Stefan Jopp、Norbert Steinfeld、Tariel V. Ghochikyan、Ashot S. Saghyan、Christine Fischer、Peter Langer

  DOI：10.1002/cctc.201300099

  日期：2013.8

  The palladium‐catalyzed CH activation and arylation of N‐methylpyrrole and N‐phenylpyrrole allowed a convenient synthesis of diarylpyrroles. The reactions were performed by using tetrabutylammonium acetate as an ionic solvent, which allowed for the application of a ligand‐free catalytic system by using simple palladium salts or polyvinylpyrrolidone‐stabilized palladium nanoparticles as the catalyst

  钯催化的CH活化和N-甲基吡咯和N-苯基吡咯的芳基化使得二芳基吡咯的合成方便。反应是通过使用乙酸四丁铵作为离子溶剂进行的，该反应可以通过使用简单的钯盐或聚乙烯吡咯烷酮稳定的钯纳米颗粒作为催化剂来应用无配体的催化体系。
• Palladium-Catalysed Direct Polyarylation of Pyrrole Derivatives
  作者：Liqin Zhao、Christian Bruneau、Henri Doucet

  DOI：10.1002/cctc.201200521

  日期：2013.1

  palladium‐catalysed direct polyarylation of 1‐methylpyrrole and 1‐phenylpyrrole was studied. As the C2 and C5 positions of pyrroles are more reactive for CH bond functionalisation than the C3 and C4 positions, the formation of 2,5‐diarylpyrroles was found to proceed selectively in the presence of 3 equiv. of a variety of aryl bromides. The sequential C2 arylation followed by C5 arylation to prepare non‐symmetrically

  研究了钯催化的1-甲基吡咯和1-苯基吡咯的直接聚芳基化反应。由于吡咯的C2和C5位置比C3和C4位置对CH键功能化的反应性更高，因此发现在3当量的存在下2,5-二芳基吡咯的形成选择性进行。各种芳基溴化物。还研究了顺序C2芳基化，然后进行C5芳基化以制备非对称取代的2,5-二芳基吡咯。对于此类吡咯的合成，与缺电子的芳基溴化物的偶联可获得更高的收率。还实现了1-甲基吡咯的四芳基化。从4当量 由3,5-双（三氟甲基）溴苯得到的2,3,4,5-四芳基吡咯收率很高。
• Synthesis of some diguanidino 1-methyl-2,5-diaryl-1H-pyrroles as antifungal agents
  作者：Gour Hari Jana、Sanjay Jain、Sudershan K. Arora、Neelima Sinha

  DOI：10.1016/j.bmcl.2005.05.080

  日期：2005.8

  A series of novel 2,5-bis(guanidino-aryl)-1-methyl-1H-pyrroles 9a-h has been synthesized starting from 1-methyl-1H-pyrrole. The antifungal activities of compounds were evaluated by in vitro agar diffusion and broth dilution assay against Candida spp. and Aspergillus spp. Compound 9c from this series was found to be equipotent or more potent than fluconazole, whereas compound 9d was comparable to fluconazole

  从1-甲基-1H-吡咯开始合成了一系列新颖的2，5-双（胍基-芳基）-1-甲基-1H-吡咯9a-h。通过体外琼脂扩散和肉汤稀释试验对念珠菌的抗真菌活性进行了评估。和曲霉属。发现该系列化合物9c与氟康唑同等或更有效，而针对大多数测试菌株，化合物9d与氟康唑相当。