3,4-bis(2-methylbenzo[b]thiophen-3-yl)-1H-pyrrole-2,5-dione | 1034806-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3,4-bis(2-methylbenzo[b]thiophen-3-yl)-1H-pyrrole-2,5-dione
• 英文别名: 3,4-Bis(2-methyl-1-benzothiophen-3-yl)pyrrole-2,5-dione；3,4-bis(2-methyl-1-benzothiophen-3-yl)pyrrole-2,5-dione
• CAS: 1034806-13-7
• 化学式: C₂₂H₁₅NO₂S₂
• 分子量: 389.499
• InChiKey: SOKYMEBHFVTGJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(2-methylbenzo[b]thiophen-3-yl)-1H-pyrrole-2,5-dione 生成
  参考文献：
  名称：

  On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution

  摘要：

  A series of photochromic diarylmaleimide derivatives has been synthesized and studied with respect to the photochromic properties in aqueous solution. The main rationale is to investigate if these compounds could be used as photoswitchable units in biological contexts, motivated by the fact that the diarylmaleimide structural motif is identified in many pharmacophores. Thus, photoswitchable variants of this class of compounds could be very useful in the quest for photoactivatable drugs. The photoinduced cyclization reaction (colorization) is suppressed in solvents of high polarity, whereas the ring-opening reaction (decolorization) still occurs with high efficiency. The photochromically active anti-parallel conformer of the open form is more abundant in the asymmetrically substituted derivatives, which in turn favors the formation of the closed isomeric form. The rates of the thermal isomerization reactions have also been assessed, together with the resistance toward thermal degradation. Here it was observed that the maleimide derived compounds were not susceptible to the thermally driven reactions (hydrolysis and isomerization). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.10.023
• 作为产物：
  描述：

  1,2-bis(2-methylbenzothiophene-3-yl)maleic anhydride 在 六甲基二硅氮烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3,4-bis(2-methylbenzo[b]thiophen-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  二芳基乙烯光致变色中的三重途径：含钌（II）多吡啶和 1,2-双（2-甲基苯并噻吩-3-基）马来酰亚胺单元的二元组的光物理和计算研究

  摘要：

  1,2-双（2-甲基苯并噻吩-3-基）马来酰亚胺模型（DAE）和两个二元组，其中该光致变色单元通过直接的氮 - 碳键（Ru-DAE）或通过插入的亚甲基（ Ru-CH 2-DAE ), 到钌多吡啶发色团已被合成。这些系统的光化学和光物理学已通过固定和时间分辨（纳秒和飞秒）光谱方法的组合在乙腈中得到彻底表征。二芳基乙烯模型 DAE 通过在 448 nm 处激发进行光环化，在静止状态下光转化率为 35%。脱气后量子产率从 0.22 增加到 0.33。光化学循环回复（量子产率，0.51）可在 λ > 500 nm 激发后进行至完成。光环化发生在激发单线态 (S 1)，作为超快（约 0.5 ps）过程，以及从三线态 (T 1) 在微秒时间尺度内发生。在 Ru-DAE 和 Ru-CH 2-DAE 二元组中，在被钌发色团光吸收后发生有效的光环化反应，具有氧敏感的量子产率（在脱气和充气溶液中分别为 0.44

  DOI：

  10.1021/ja711173z

文献信息

• Triplet Pathways in Diarylethene Photochromism: Photophysical and Computational Study of Dyads Containing Ruthenium(II) Polypyridine and 1,2-Bis(2-methylbenzothiophene-3-yl)maleimide Units
  作者：Maria Teresa Indelli、Stefano Carli、Marco Ghirotti、Claudio Chiorboli、Marcella Ravaglia、Marco Garavelli、Franco Scandola

  DOI：10.1021/ja711173z

  日期：2008.6.1

  time-resolved spectroscopy. Besides prompt photocyclization (0.5 ps), fast singlet energy transfer takes place from the excited diarylethene to the Ru(II) chromophore (30 ps in Ru-DAE, 150 ps in Ru-CH 2-DAE ). In the Ru(II) chromophore, prompt intersystem crossing to the MLCT triplet state is followed by triplet energy transfer to the diarylethene (1.5 ns in Ru-DAE, 40 ns in Ru-CH 2-DAE ). The triplet

  1,2-双（2-甲基苯并噻吩-3-基）马来酰亚胺模型（DAE）和两个二元组，其中该光致变色单元通过直接的氮 - 碳键（Ru-DAE）或通过插入的亚甲基（ Ru-CH 2-DAE ), 到钌多吡啶发色团已被合成。这些系统的光化学和光物理学已通过固定和时间分辨（纳秒和飞秒）光谱方法的组合在乙腈中得到彻底表征。二芳基乙烯模型 DAE 通过在 448 nm 处激发进行光环化，在静止状态下光转化率为 35%。脱气后量子产率从 0.22 增加到 0.33。光化学循环回复（量子产率，0.51）可在 λ > 500 nm 激发后进行至完成。光环化发生在激发单线态 (S 1)，作为超快（约 0.5 ps）过程，以及从三线态 (T 1) 在微秒时间尺度内发生。在 Ru-DAE 和 Ru-CH 2-DAE 二元组中，在被钌发色团光吸收后发生有效的光环化反应，具有氧敏感的量子产率（在脱气和充气溶液中分别为 0.44
• Chromo-pharmacophores: photochromic diarylmaleimide inhibitors for sirtuins
  作者：C. Falenczyk、M. Schiedel、B. Karaman、T. Rumpf、N. Kuzmanovic、M. Grøtli、W. Sippl、M. Jung、B. König

  DOI：10.1039/c4sc01346h

  日期：——

  Controlling the activity of sirtuins is of high biomedical relevance as the enzymes are involved in cancer, neurodegeneration and other diseases.

  控制去乙酰化酶的活性在生物医学上具有很高的重要性，因为这些酶参与了癌症、神经退行性疾病和其他疾病。
• On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution
  作者：Cassandra Fleming、Patricia Remón、Shiming Li、Nadja Anita Simeth、Burkhard König、Morten Grøtli、Joakim Andréasson

  DOI：10.1016/j.dyepig.2016.10.023

  日期：2017.2

  A series of photochromic diarylmaleimide derivatives has been synthesized and studied with respect to the photochromic properties in aqueous solution. The main rationale is to investigate if these compounds could be used as photoswitchable units in biological contexts, motivated by the fact that the diarylmaleimide structural motif is identified in many pharmacophores. Thus, photoswitchable variants of this class of compounds could be very useful in the quest for photoactivatable drugs. The photoinduced cyclization reaction (colorization) is suppressed in solvents of high polarity, whereas the ring-opening reaction (decolorization) still occurs with high efficiency. The photochromically active anti-parallel conformer of the open form is more abundant in the asymmetrically substituted derivatives, which in turn favors the formation of the closed isomeric form. The rates of the thermal isomerization reactions have also been assessed, together with the resistance toward thermal degradation. Here it was observed that the maleimide derived compounds were not susceptible to the thermally driven reactions (hydrolysis and isomerization). (C) 2016 Elsevier Ltd. All rights reserved.