5-(4-dimethylaminophenyl)-1-methylpyrrole-2-carbaldehyde | 1088704-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-dimethylaminophenyl)-1-methylpyrrole-2-carbaldehyde
• 英文别名: 5-(4-dimethylaminophenyl)-1-methyl-2-formylpyrrole；5-(4-dimethylaminophenyl)-1-methyl-1H-pyrrole-2-carboxaldehyde；5-[4-(Dimethylamino)phenyl]-1-methylpyrrole-2-carbaldehyde；5-[4-(dimethylamino)phenyl]-1-methylpyrrole-2-carbaldehyde
• CAS: 1088704-64-6
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: FBLWAEZAMWZWOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基苯并噻唑 、 5-(4-dimethylaminophenyl)-1-methylpyrrole-2-carbaldehyde 在 氢氧化钾 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以43%的产率得到(E)-2-{2-[5-(4-dimethylaminophenyl)-1-methylpyrrol-2-yl]-vinyl}-benzothiazole
  参考文献：
  名称：

  Donor–π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity

  摘要：

  A series of novel derivatives containing an electron-donating N,N-dimethylaminophenyl ring connected to an electron-withdrawing benzothiazole or benzothiazolium moiety via a heteroaryl system (furan, thiophene or N-methylpyrrole) and up to two ethenylene groups have been synthesized and characterized. Furthermore, their nonlinear optical (NLO) properties have been investigated at the theoretical level using DFT and time-dependent DFT methods, and their antimicrobial activities were evaluated against a standard set of unicellular organisms. Both benzothiazole and benzothiazolium systems are predicted to exhibit large NLO responses, based on the calculated static molecular quadratic hyper-polarizabilities beta(0) as well as intramolecular charge transfer (ICT) transition characteristics. Moreover, the 3-alkyl-benzothiazolium salts were found to display high toxicity against several tested microbes. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.064
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 4-溴-N,N-二甲基苯胺 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 17.0h， 以71%的产率得到5-(4-dimethylaminophenyl)-1-methylpyrrole-2-carbaldehyde
  参考文献：
  名称：

  使用无配体的钯催化剂将吡咯与芳族溴化物进行区域选择性的C-2或C-5直接芳基化

  摘要：

  据报道，通过CH键活化，吡咯的区域选择性C-2或C-5芳基化的简单且经济的方法。仅使用0.5-0.01 mol％的市售且无空气稳定的无配体的乙酸钯（II）[Pd（OAc）2 ]作为催化剂。容许在吡咯的C-2位置存在吸电子取代基，例如甲酰基，乙酰基或酯。还已经发现这种对环境有吸引力的方法可耐受芳基溴化物上的各种官能团，例如甲酰基，乙酰基，丙酰基，酯，腈，硝基，氟，甲氧基，氨基或三氟甲基。

  DOI：

  10.1002/adsc.200900196

文献信息

• Broad Spectrum Antiviral and Antiparasitic Agents
  申请人：Lee Benhur

  公开号：US20130028966A1

  公开（公告）日：2013-01-31

  The invention provides compounds represented by the formulae: (I) and (II) where the compounds are useful in treating, for example, viral and/or parasitic infections. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds.

  本发明提供了公式（I）和（II）所代表的化合物，这些化合物可用于治疗病毒和/或寄生虫感染等疾病。本发明还提供了包含这些化合物的制药组合物以及使用这些化合物进行治疗的方法。
• BROAD SPECTRUM ANTIVIRAL AND ANTIPARASITIC AGENTS
  申请人：The Regents of the University of California

  公开号：US20160207908A1

  公开（公告）日：2016-07-21

  The invention provides compounds represented by the formulae: (I) and (II) where the compounds are useful in treating, for example, viral and/or parasitic infections. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment using the compounds.

  该发明提供了由公式（I）和（II）表示的化合物，这些化合物在治疗例如病毒性和/或寄生虫感染方面非常有用。还提供了包含这些化合物的药物组合物以及使用这些化合物的治疗方法。
• US9139575B2
  申请人：——

  公开号：US9139575B2

  公开（公告）日：2015-09-22
• Regioselective C-2 or C-5 Direct Arylation of Pyrroles with Aryl Bromides using a Ligand-Free Palladium Catalyst
  作者：Julien Roger、Henri Doucet

  DOI：10.1002/adsc.200900196

  日期：——

  acetyl or ester at the C-2 position of the pyrrole is tolerated. This environmentally attractive procedure has also been found to be tolerant to a very wide variety of functional groups on the aryl bromides such as formyl, acetyl, propionyl, ester, nitrile, nitro, fluoro, methoxy, amino or trifluoromethyl.

  据报道，通过CH键活化，吡咯的区域选择性C-2或C-5芳基化的简单且经济的方法。仅使用0.5-0.01 mol％的市售且无空气稳定的无配体的乙酸钯（II）[Pd（OAc）2 ]作为催化剂。容许在吡咯的C-2位置存在吸电子取代基，例如甲酰基，乙酰基或酯。还已经发现这种对环境有吸引力的方法可耐受芳基溴化物上的各种官能团，例如甲酰基，乙酰基，丙酰基，酯，腈，硝基，氟，甲氧基，氨基或三氟甲基。
• Donor–π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity
  作者：Marián Zajac、Peter Hrobárik、Peter Magdolen、Pavlína Foltínová、Pavol Zahradník

  DOI：10.1016/j.tet.2008.08.064

  日期：2008.11

  A series of novel derivatives containing an electron-donating N,N-dimethylaminophenyl ring connected to an electron-withdrawing benzothiazole or benzothiazolium moiety via a heteroaryl system (furan, thiophene or N-methylpyrrole) and up to two ethenylene groups have been synthesized and characterized. Furthermore, their nonlinear optical (NLO) properties have been investigated at the theoretical level using DFT and time-dependent DFT methods, and their antimicrobial activities were evaluated against a standard set of unicellular organisms. Both benzothiazole and benzothiazolium systems are predicted to exhibit large NLO responses, based on the calculated static molecular quadratic hyper-polarizabilities beta(0) as well as intramolecular charge transfer (ICT) transition characteristics. Moreover, the 3-alkyl-benzothiazolium salts were found to display high toxicity against several tested microbes. (c) 2008 Elsevier Ltd. All rights reserved.