2,3,8-trimethylbisthiazolo[4,5-e;5,4-g]1,3-benzothiazole | 1401521-95-6

• 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: 2,3,8-trimethylbisthiazolo[4,5-e;5,4-g]1,3-benzothiazole
• 英文别名: 2,5,8-Trimethylbenzo[1,2-d:3,4-da(2):6,5-da(2)a(2)]tristhiazole；4,9,14-trimethyl-3,8,15-trithia-5,10,13-triazatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,9,11,13-hexaene
• CAS: 1401521-95-6
• 化学式: C₁₂H₉N₃S₃
• 分子量: 291.422
• InChiKey: IMGHAIBCMMHVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,8-trimethylbisthiazolo[4,5-e;5,4-g]1,3-benzothiazole 以 甲醇 为溶剂， 115.0~120.0 ℃ 、1.2 MPa 条件下， 反应 2.17h， 生成 2-{(E)-2-[4-(diphenylamino)phenyl]vinyl}-3,5,8-trimethylbisthiazolo[4,5-e:5',4'-g]-1,3-benzothiazolium iodide
  参考文献：
  名称：

  Benzotristhiazole based chromophores for nonlinear optics

  摘要：

  Methylation of unsymmetrical trimethylbenzotristhiazole with various reagents has been studied in details. The structure of obtained 2,3,5,8-tetramethylbisthiazolo[4,5-e;5,4-g]-1,3-benzothiazolium iodide has been proved by X-ray analysis in accord with the quantum-chemical calculations at DFT-B3LYP level. The electron-withdrawing tetramethylbenzotristhiazolium building block was submitted to Knoevenagel reaction with aromatic aldehydes containing an electron-releasing group. This led to a series of condensation products with push-pull structure. Relations between structure, linear (UV-Vis and fluorescence spectra) and nonlinear optical properties (calculated frontier orbital energy gap, BLA index, hyperpolarizabilities beta and gamma have been investigated. (C) 2012 Published by Elsevier B.V.

  DOI：

  10.1016/j.molstruc.2012.06.018
• 作为产物：
  描述：

  2-methyl-4,6-dinitrobenzothiazole 在 劳森试剂 、 盐酸 、 4-二甲氨基吡啶 、 铁粉 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 20.0~110.0 ℃ 、400.01 kPa 条件下， 反应 20.93h， 生成 2,3,8-trimethylbisthiazolo[4,5-e;5,4-g]1,3-benzothiazole
  参考文献：
  名称：

  不对称苯并噻唑：八极发色团的新型吸电子核

  摘要：

  已开发出不对称三甲基苯并噻唑的六步合成法。从硝化，还原，乙酰化，硫代化和两倍环化后的2-甲基苯并噻唑开始，可以高收率获得所需的三甲基苯并噻吩并噻唑。它与供体取代的苯甲醛的缩合为新的八极发色团提供了途径。由二硝基苯胺合成这种苯并噻吩并噻唑的尝试失败了。该过程提供了新的苯并咪唑衍生物。

  DOI：

  10.1002/jhet.1530

文献信息

• Benzotristhiazole based chromophores for nonlinear optics
  作者：Andrea Fülöpová、Peter Magdolen、Ivica Sigmundová、Pavol Zahradník、Erik Rakovský、Marek Cigáň

  DOI：10.1016/j.molstruc.2012.06.018

  日期：2012.11

  Methylation of unsymmetrical trimethylbenzotristhiazole with various reagents has been studied in details. The structure of obtained 2,3,5,8-tetramethylbisthiazolo[4,5-e;5,4-g]-1,3-benzothiazolium iodide has been proved by X-ray analysis in accord with the quantum-chemical calculations at DFT-B3LYP level. The electron-withdrawing tetramethylbenzotristhiazolium building block was submitted to Knoevenagel reaction with aromatic aldehydes containing an electron-releasing group. This led to a series of condensation products with push-pull structure. Relations between structure, linear (UV-Vis and fluorescence spectra) and nonlinear optical properties (calculated frontier orbital energy gap, BLA index, hyperpolarizabilities beta and gamma have been investigated. (C) 2012 Published by Elsevier B.V.
• Unsymmetrical Benzotristhiazole: A New Electron-Withdrawing Core for Octupolar Chromophores
  作者：Andrea Fülöpová、Peter Magdolen、Miroslava Károlyiová、Ivica Sigmundová、Pavol Zahradník

  DOI：10.1002/jhet.1530

  日期：2013.5

  A six‐step synthesis of the unsymmetrical trimethylbenzotristhiazole has been developed. Starting from 2‐methylbenzothiazole following nitration, reduction, acetylation, thionation, and twofold cyclization, the desired trimethylbenzotristhiazole was obtained in good yield. Its condensation with donor‐substituted benzaldehydes presents the way to new octupolar chromophores. The attempt to synthesize

  已开发出不对称三甲基苯并噻唑的六步合成法。从硝化，还原，乙酰化，硫代化和两倍环化后的2-甲基苯并噻唑开始，可以高收率获得所需的三甲基苯并噻吩并噻唑。它与供体取代的苯甲醛的缩合为新的八极发色团提供了途径。由二硝基苯胺合成这种苯并噻吩并噻唑的尝试失败了。该过程提供了新的苯并咪唑衍生物。