1-(2-chlorophenyl)-2,5-dimethyl-1H-pyrrole | 560995-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-chlorophenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 1-(2-chlorobenzyl)-2,5-dimethyl-1H-pyrrole；1-[(2-chlorophenyl)methyl]-2,5-dimethyl-1H-pyrrole；1-[(2-chlorophenyl)methyl]-2,5-dimethylpyrrole
• CAS: 560995-32-6
• 化学式: C₁₃H₁₄ClN
• mdl: MFCD04606973
• 分子量: 219.714
• InChiKey: CJCMJPGNMBFFDC-UHFFFAOYSA-N

物化性质

• 溶解度：
  1.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  1-(2-chlorophenyl)-2,5-dimethyl-1H-pyrrole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 以68%的产率得到1-(2-chlorobenzyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarbaldehyde
  参考文献：
  名称：

  Design and development of pyrrole carbaldehyde: an effective pharmacophore for enoyl-ACP reductase

  摘要：

  Enoyl-ACP reductase is the key enzyme involved in FAS-II synthesis of mycolic acid in bacterial cell wall and is a promising target for discovering new chemical entity. The designed pharmacophores are the possible better tools to combat mutation in enoyl-ACP enzyme, which leads to a decrease in volume of triclosan binding site. Compound 3a showed H-bonding interactions similar to that of triclosan with enoyl-ACP enzyme and with a better docking score (C score 8.81), while the compound 3f showed additional interaction with MET98.H amino acid residue. The 3D-QSAR computations also support the docking study to develop novel pyrrole-based derivatives.Molecular docking 3D-QSAR studies and synthesis of active analogs of pyrrole carbaldehyde as better receptor fit pharmacophore for enoyl-ACP reductase along with in vitro antitubercular activity.

  DOI：

  10.1007/s00044-016-1517-y
• 作为产物：
  描述：

  2,5-己二酮 、 邻氯苯甲胺 在 sulfuric acid-supported silica-coated maghemite γ-Fe₂O₃ nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 12.0h， 以78%的产率得到1-(2-chlorophenyl)-2,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Nanomagnetically Modified Sulfuric Acid (γ-Fe2O3@SiO2-OSO3H): An Efficient, Fast, and Reusable Catalyst for Greener Paal–Knorr Pyrrole Synthesis

  摘要：

  Paal-Knorr pyrrole synthesis was performed in the presence of superparamagnetic nanoparticles of modified sulfuric acid (gamma-Fe2O3@SiO2-OSO3H) as an efficient and magnetically separable catalyst. Recovery of the catalyst was simple using a magnet, allowing its reuse without significant loss of its catalytic activity (over five cycles).

  DOI：

  10.1007/s10562-014-1197-5

文献信息

• Copper/Nitroxyl-Catalyzed Synthesis of Pyrroles by Oxidative Coupling of Diols and Primary Amines at Room Temperature
  作者：Weiru Fu、Lina Zhu、Shangzhi Tan、Zhengjia Zhao、Xiangzhu Yu、Lianyue Wang

  DOI：10.1021/acs.joc.2c01646

  日期：2022.10.7

  The Cu/ABNO-catalyzed aerobic oxidative coupling of diols and primary amines to access N-substituted pyrroles is highlighted (ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl). The reaction proceeds at room temperature with an O2 balloon as the oxidant using commercially available materials as the substrates and catalysts. The catalyst system is characterized by a broad range of substrates and a good tolerance

  突出显示了 Cu/ABNO 催化的二醇和伯胺的需氧氧化偶联以获得 N 取代的吡咯（ABNO = 9-氮杂双环 [3.3.1] 壬烷N-氧基）。反应在室温下以 O 2气球作为氧化剂进行，使用市售材料作为底物和催化剂。该催化剂体系的特点是广泛的底物和对敏感官能团的良好耐受性。克级实验证明了该系统的实用性。
• Nanomagnetically Modified Sulfuric Acid (γ-Fe2O3@SiO2-OSO3H): An Efficient, Fast, and Reusable Catalyst for Greener Paal–Knorr Pyrrole Synthesis
  作者：Samaneh Cheraghi、Dariush Saberi、Akbar Heydari

  DOI：10.1007/s10562-014-1197-5

  日期：2014.7

  Paal-Knorr pyrrole synthesis was performed in the presence of superparamagnetic nanoparticles of modified sulfuric acid (gamma-Fe2O3@SiO2-OSO3H) as an efficient and magnetically separable catalyst. Recovery of the catalyst was simple using a magnet, allowing its reuse without significant loss of its catalytic activity (over five cycles).
• Design and development of pyrrole carbaldehyde: an effective pharmacophore for enoyl-ACP reductase
  作者：Shrinivas D. Joshi、Devendra Kumar、Uttam A. More、Kap Seung Yang、Tejraj M. Aminabhavi

  DOI：10.1007/s00044-016-1517-y

  日期：2016.4

  Enoyl-ACP reductase is the key enzyme involved in FAS-II synthesis of mycolic acid in bacterial cell wall and is a promising target for discovering new chemical entity. The designed pharmacophores are the possible better tools to combat mutation in enoyl-ACP enzyme, which leads to a decrease in volume of triclosan binding site. Compound 3a showed H-bonding interactions similar to that of triclosan with enoyl-ACP enzyme and with a better docking score (C score 8.81), while the compound 3f showed additional interaction with MET98.H amino acid residue. The 3D-QSAR computations also support the docking study to develop novel pyrrole-based derivatives.Molecular docking 3D-QSAR studies and synthesis of active analogs of pyrrole carbaldehyde as better receptor fit pharmacophore for enoyl-ACP reductase along with in vitro antitubercular activity.