13,13′-[(2,5-bis((E)-4-vinylstyryl)-1,4-phenylene)bis(oxy)]bis-(2,5,8,11,15,18,21,24-octaoxapentacosane) | 1616337-74-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 13,13′-[(2,5-bis((E)-4-vinylstyryl)-1,4-phenylene)bis(oxy)]bis-(2,5,8,11,15,18,21,24-octaoxapentacosane)
• CAS: 1616337-74-6
• 化学式: C₆₀H₉₀O₁₈
• 分子量: 1099.36
• InChiKey: HVLUVMBLQFMTGG-XPWSMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  78.0
• 可旋转键数：
  54.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  166.14
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  13,13′-[(2,5-bis((E)-4-vinylstyryl)-1,4-phenylene)bis(oxy)]bis-(2,5,8,11,15,18,21,24-octaoxapentacosane) 、 1,3-二噁戊环,2-(4-碘苯基)- 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以38%的产率得到2,2′-(((1E,1′E)-(((1E,1′E)-(2,5-bis(2,5,8,11,15,18,21,24-octaoxapentacosan-13-yloxy)-1,4-phenylene)bis(ethene-2,1-diyl))-bis(4,1-phenylene))bis(ethene-2,1-diyl))bis(4,1-phenylene))-bis(1,3-dioxolane)
  参考文献：
  名称：

  Detection of Amines with Extended Distyrylbenzenes by Strip Assays

  摘要：

  We herein describe the synthesis and property evaluation of three novel aldehyde-substituted pentameric phenylenevinylenes carrying branched oligo(ethylene glycol) (swallowtail, Sw) substituents. The targets were synthesized by a combination of Heck coupling and Wittig or Homer reactions of suitable precursor modules. If the pentameric phenylenevinylene carries only two of these Sw substituents, it is no longer water-soluble. When six of the Sw substituents are attached, regardless of their position, the pentameric phenylenevinylenes are well water-soluble. The dialdehydes were investigated with respect to their amine-sensing capabilities both in water as well as in the solid state, sprayed onto thin layer chromatography (TLC) plates (alox, silica gel, reversed phase silica gel). The recognition of amine vapors using the sprayed-on phenylenevinylene dialdehydes is superb and allows the identification of different amines on regular silica TLC plates via color changes, analyzed by a statistical tool, the multivariate analysis of variance (MANOVA) protocol.

  DOI：

  10.1021/jo501129d
• 作为产物：
  描述：

  4,4′-((1E,1′E)-(2,5-bis(2,5,8,11,15,18,21,24-octaoxapentacosan-13-yloxy)-1,4-phenylene)bis(ethene-2,1-diyl))dibenzaldehyde 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到13,13′-[(2,5-bis((E)-4-vinylstyryl)-1,4-phenylene)bis(oxy)]bis-(2,5,8,11,15,18,21,24-octaoxapentacosane)
  参考文献：
  名称：

  Detection of Amines with Extended Distyrylbenzenes by Strip Assays

  摘要：

  We herein describe the synthesis and property evaluation of three novel aldehyde-substituted pentameric phenylenevinylenes carrying branched oligo(ethylene glycol) (swallowtail, Sw) substituents. The targets were synthesized by a combination of Heck coupling and Wittig or Homer reactions of suitable precursor modules. If the pentameric phenylenevinylene carries only two of these Sw substituents, it is no longer water-soluble. When six of the Sw substituents are attached, regardless of their position, the pentameric phenylenevinylenes are well water-soluble. The dialdehydes were investigated with respect to their amine-sensing capabilities both in water as well as in the solid state, sprayed onto thin layer chromatography (TLC) plates (alox, silica gel, reversed phase silica gel). The recognition of amine vapors using the sprayed-on phenylenevinylene dialdehydes is superb and allows the identification of different amines on regular silica TLC plates via color changes, analyzed by a statistical tool, the multivariate analysis of variance (MANOVA) protocol.

  DOI：

  10.1021/jo501129d