2-pentafluorobuta-1,3-dienyl-benzothiazole | 1226903-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-pentafluorobuta-1,3-dienyl-benzothiazole
• 英文别名: 1-(2-benzothiazolyl)-pentafluoro-1,3-butadiene
• CAS: 1226903-94-1
• 化学式: C₁₁H₄F₅NS
• 分子量: 277.217
• InChiKey: MPUQYYUBDQQIHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-pentafluorobuta-1,3-dienyl-benzothiazole 、 碘甲烷 在 silver tetrafluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2-(pentafluoro-1,3-butadienyl)-3-methyl benzothiazolium tetrafluoroborate
  参考文献：
  名称：

  Synthesis of the first representative of dicarbothiacyanine dyes with completely fluorinated polymethine chain

  摘要：

  2-Iodobenzothiazole was reacted with tributyl(pentafluorobutadienyl)tin in the Stille reaction conditions to give 2-pentafluorobutadienylbenzothiazole 1. The quaternary salt of 1 via interaction with 2-fluoromethylbenzothiazole methylene base, obtained in situ, forms two cyanine dyes 8 and 9 as a result of nucleophilic attack of two different positions of perfluorobutadiene chain. The pure 2-fluoromethylbenzothiazole methylene base (in a dimer form) was obtained by deprotonation of the corresponding salt by NaH and on reacting with I forms the dye base 11 that underwent electrocyclization and subsequent HF addition to form the cyclohexadiene 12 identified by X-ray analysis data. Upon quaternization and HF abstraction by toluidine the recyclization occurred and dye 8 - the first representative of dicarbothiacyanine dyes with perfluorinated polymethine chain - was obtained. It has lambda(max) = 691 nm, that is 41 nm more than in non fluorinated dye, vinylene shift is equal to 111 nm. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.012
• 作为产物：
  描述：

  2-碘苯并噻唑 、 C₁₆H₂₇F₅Sn 在 四(三苯基膦)钯 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以66.8%的产率得到2-pentafluorobuta-1,3-dienyl-benzothiazole
  参考文献：
  名称：

  Synthesis of the first representative of dicarbothiacyanine dyes with completely fluorinated polymethine chain

  摘要：

  2-Iodobenzothiazole was reacted with tributyl(pentafluorobutadienyl)tin in the Stille reaction conditions to give 2-pentafluorobutadienylbenzothiazole 1. The quaternary salt of 1 via interaction with 2-fluoromethylbenzothiazole methylene base, obtained in situ, forms two cyanine dyes 8 and 9 as a result of nucleophilic attack of two different positions of perfluorobutadiene chain. The pure 2-fluoromethylbenzothiazole methylene base (in a dimer form) was obtained by deprotonation of the corresponding salt by NaH and on reacting with I forms the dye base 11 that underwent electrocyclization and subsequent HF addition to form the cyclohexadiene 12 identified by X-ray analysis data. Upon quaternization and HF abstraction by toluidine the recyclization occurred and dye 8 - the first representative of dicarbothiacyanine dyes with perfluorinated polymethine chain - was obtained. It has lambda(max) = 691 nm, that is 41 nm more than in non fluorinated dye, vinylene shift is equal to 111 nm. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.012