(E)-2-{2-[5-(4-dimethylaminophenyl)-1-methylpyrrol-2-yl]vinyl}-3-methylbenzothiazolium iodide | 1088704-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (E)-2-{2-[5-(4-dimethylaminophenyl)-1-methylpyrrol-2-yl]vinyl}-3-methylbenzothiazolium iodide
• 英文别名: N,N-dimethyl-4-[1-methyl-5-[2-(3-methyl-1,3-benzothiazol-3-ium-2-yl)ethenyl]pyrrol-2-yl]aniline;iodide
• CAS: 1088704-80-6
• 化学式: C₂₃H₂₄N₃S*I
• 分子量: 501.434
• InChiKey: MLMCPGPROSDNCA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-dimethylaminophenyl)-1-methylpyrrole-2-carbaldehyde 、 2,3-二甲基苯并噻唑鎓碘化物 在 吡啶 作用下， 以 甲醇 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}-3-methylbenzothiazolium iodide
  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

文献信息

• 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.