(E)-2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-benzothiazole | 1088704-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-benzothiazole
• 英文别名: 4-[(E)-2-[5-(1,3-benzothiazol-2-yl)-1-methylpyrrol-2-yl]ethenyl]-N,N-dimethylaniline
• CAS: 1088704-68-0
• 化学式: C₂₂H₂₁N₃S
• 分子量: 359.495
• InChiKey: YITIFDBLMKSFRV-JLHYYAGUSA-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：

  5-(benzothiazol-2-yl)-1-methylpyrrole-2-carbaldehyde 、 4-(N,N-dimethylamino)benzyltriphenylphosphonium iodide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (Z)-2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-benzothiazole 、 (E)-2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-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.