(E)-2-{2-[5-(4-dimethylaminophenyl)-1-methylpyrrol-2-yl]-vinyl}-benzothiazole | 1088704-71-5

• 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}-benzothiazole
• 英文别名: 4-[5-[(E)-2-(1,3-benzothiazol-2-yl)ethenyl]-1-methylpyrrol-2-yl]-N,N-dimethylaniline
• CAS: 1088704-71-5
• 化学式: C₂₂H₂₁N₃S
• 分子量: 359.495
• InChiKey: FNZPNCWWLXUIOB-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  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

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.