(E,E)-2-(2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-vinyl)-3-(prop-2-enyl)-benzothiazolium bromide | 1088704-86-2

• 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,E)-2-(2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-vinyl)-3-(prop-2-enyl)-benzothiazolium bromide
• 英文别名: N,N-dimethyl-4-[2-[1-methyl-5-[2-(3-prop-2-enyl-1,3-benzothiazol-3-ium-2-yl)ethenyl]pyrrol-2-yl]ethenyl]aniline;bromide
• CAS: 1088704-86-2
• 化学式: Br*C₂₇H₂₈N₃S
• 分子量: 506.509
• InChiKey: IVBJBZWPSUJCBY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (E)-5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrole-2-carbaldehyde 、 3-allyl-2-methylbenzothiazolium bromide 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以54%的产率得到(E,E)-2-(2-{5-[2-(4-dimethylaminophenyl)-vinyl]-1-methylpyrrol-2-yl}-vinyl)-3-(prop-2-enyl)-benzothiazolium bromide
  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.