1-(2-氟苯基)-2,5-二甲基吡咯 | 146135-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(2-氟苯基)-2,5-二甲基吡咯
• 英文名称: 1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 1-(2-Fluorophenyl)-2,5-dimethylpyrrole
• CAS: 146135-20-8
• 化学式: C₁₂H₁₂FN
• mdl: MFCD07429174
• 分子量: 189.232
• InChiKey: BFSXBLWSHDADPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

SDS

1-(2-fluorophenyl)-2,5-dimethylpyrroleMSDS英文版

反应信息

• 作为反应物：
  描述：

  1-(2-氟苯基)-2,5-二甲基吡咯 在 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 18.33h， 生成 N-[[1-(2-fluorophenyl)-2,5-dimethylpyrrol-3-yl]methyl]cyclohexanamine
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515
• 作为产物：
  描述：

  2-氟苯胺 、 2,5-己二酮 在 amberlite IR 120 acidic resin 作用下， 反应 0.5h， 以99%的产率得到1-(2-氟苯基)-2,5-二甲基吡咯
  参考文献：
  名称：

  使用可回收 Amberlite IR 120 酸性树脂合成 Paal-Knorr 吡咯：一种绿色方法

  摘要：

  摘要 Amberlite IR 120 酸性树脂是一种聚合物基质，已被证明可作为 2,5-己二酮与伯胺在无溶剂条件下进行 Paal-Knorr 缩合的催化剂。这是一种用于 N 取代吡咯衍生物的高效、温和且绿色的方法。图形概要

  DOI：

  10.1080/00397911.2010.540766

文献信息

• Bio-based Material as Medium, Mild and Reusable Catalyst for Paal– Knorr Pyrrole Synthesis with and Without Ultrasonic Irradiation
  作者：Abha Sharma、Illa Siva Kalyani、Anam Fatima

  DOI：10.2174/1570178614666170711145253

  日期：2018.2.7

  a simple, mild and speedy synthesis of N-substituted 2,5-dimethyl pyrrole derivatives in ‘’GAAS’’ as medium and catalyst at room temperature and under ultrasound irradiation. Results: This protocol was employed for the synthesis of various 2,5-dimethyl-N-substituted pyrrolederivatives using both aliphatic as well as aromatic amines in short time (2 to 10 minutes)with excellent yield (84-95%) at room

  背景：吡咯部分存在于天然存在的化合物（例如叶绿素，血红素和维生素B12）中，并存在于多种药物中，例如阿托伐他汀，酮咯酸，伊洛吡唑，托美汀和舒尼替尼。已经使用了多种方法来合成吡咯衍生物。然而，仍然需要环境友好和经济的协议。 方法：我们报道了在“ GAAS”中在室温和超声辐射下简单，温和，快速地合成N-取代的2,5-二甲基吡咯衍生物作为介质和催化剂。 结果：该方案用于在短时间（2至10分钟）内同时使用脂肪族和芳香族胺在室温下以优异的收率（84-95％）合成各种2,5-二甲基-N-取代的吡咯烷衍生物并在超声波照射下。催化系统“ GAAS”已有效再生并重复使用了五次，而活性并未受到重大影响。 结论：总之，我们已经开发出一种环保，简单，快速，可重复使用，温和有效的方法，用于合成N-取代的吡咯衍生物。这种基于生物的方案是一种具有成本效益的绿色方法，可用于合成具有生物活性的N-取代的吡咯衍生物。
• An efficient synthesis of N-substituted pyrroles catalyzed by MgI2 etherate
  作者：Yongdong Zhang、Guodong Weng、Jingyan Chen、Danting Ma、Xingxian Zhang

  DOI：10.1515/mgmc-2014-0031

  日期：2014.1.1

  We describe a convenient and useful procedure for the synthesis of various 2,5-dimethyl-N-substituted pyrrole derivatives by the addition of 2,5-hexadione with aromatic amines, heteroaromatic amines and aliphatic amines catalyzed by MgI

  我们描述了一种方便实用的程序，通过将2,5-己二酮与芳香胺、杂环胺和脂肪胺在MgI催化下加成，合成各种2,5-二甲基-N-取代吡咯衍生物。

• 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.
• Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1<i>H</i>-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and <i>N</i>-Adamantan-2-yl-<i>N</i>′-((<i>E</i>)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria
  作者：Sanjib Bhakta、Nicolò Scalacci、Arundhati Maitra、Alistair K. Brown、Saiprasad Dasugari、Dimitrios Evangelopoulos、Timothy D. McHugh、Parisa N. Mortazavi、Alexander Twist、Elena Petricci、Fabrizio Manetti、Daniele Castagnolo

  DOI：10.1021/acs.jmedchem.6b00031

  日期：2016.3.24

  Novel pyrroles have been designed, synthesized, and evaluated against mycobacterial strains. The pyrroles have originally been designed as hybrids of the antitubercular drugs BM212 (1) and SQ109 (2), which showed common chemical features with very similar topological distribution. A perfect superposition of the structures of 1 and 2 revealed by computational studies suggested the introduction of bulky substituents at the terminal portion of the pyrrole C3 side chain and the removal of the CS aryl moiety. Five compounds showed high activity toward Mycobacterium tuberculosis, while 9b and 9c were highly active also against multidrug-resistant clinical isolates. Compound 9c showed low eukaryotic cell toxicity, turning out to be an excellent lead candidate for preclinical trials. In addition, four compounds showed potent inhibition (comparable to that of verapamil) toward the whole-cell drug efflux pump activity of mycobacteria, thus turning out to be promising multidrug-resistance-reversing agents.