1-(3-(adamantan-1-yloxy)propyl)-[4,4'-bipyridin]-1-ium | 1349325-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-(adamantan-1-yloxy)propyl)-[4,4'-bipyridin]-1-ium
• CAS: 1349325-32-1
• 化学式: C₂₃H₂₉N₂O
• 分子量: 349.496
• InChiKey: RAKPXNNZBPGMLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(3-(adamantan-1-yloxy)propyl)-[4,4'-bipyridin]-1-ium 、 [4-[(6-bromohexyl)oxy]phenyl]phenyldiazene 以 乙腈 为溶剂， 反应 168.0h， 生成 [4-[6-[4-[1-[3-(1-Adamantyloxy)propyl]pyridin-4-ylidene]pyridin-1-yl]hexyloxoniumylidene]cyclohexa-2,5-dien-1-ylidene]-phenyliminoazanium
  参考文献：
  名称：

  Photoreversible Transformation between Seconds and Hours Time-Scales: Threading of Pillar[5]arene onto the Azobenzene-End of a Viologen Derivative

  摘要：

  Photoswitching of the transformation between seconds and hours time-scales is demonstrated using the threading of per-hydroxylated pillar[5]arene onto the azobenzene-end of a viologen derivative. When the azobenzene moiety was in the trans form, the threading of per-hydroxylated pillar[5]arene quickly took place at 25 degrees C and could not be monitored directly. The exchange rate (k) and half-life time (t(1/2)) examined by 2D EXSY NMR spectroscopy were found to be 0.209 +/- 0.013 s(-1) and 3.33 +/- 0.21 s, respectively. In contrast, the cis form of the azobenzene moiety required very long time (k = 2.14 +/- 0.27 x 10(-5) s(-1), t(1/2) = 9.13 +/- 1.2 h) to thread per-hydroxylated pillar[5]arene at 25 degrees C. Photoisomerization from the trans to the cis form generated the following increment of free energy of activation at 25 degrees C: Delta G(in)double dagger (cis form) - Delta G(in)double dagger(trans form) = 22.8 +/- 0.24 kJ mol(-1), which led to the time-scale transformation. The tuning of the threading was also accomplished by heating/cooling: the rate constants increased on heating and decreased on cooling.

  DOI：

  10.1021/jo202040p
• 作为产物：
  描述：

  4,4'-联吡啶 、 1-(3-bromopropoxy)adamantane 以 乙腈 为溶剂， 反应 7.0h， 以45%的产率得到1-(3-(adamantan-1-yloxy)propyl)-[4,4'-bipyridin]-1-ium
  参考文献：
  名称：

  Photoreversible Transformation between Seconds and Hours Time-Scales: Threading of Pillar[5]arene onto the Azobenzene-End of a Viologen Derivative

  摘要：

  Photoswitching of the transformation between seconds and hours time-scales is demonstrated using the threading of per-hydroxylated pillar[5]arene onto the azobenzene-end of a viologen derivative. When the azobenzene moiety was in the trans form, the threading of per-hydroxylated pillar[5]arene quickly took place at 25 degrees C and could not be monitored directly. The exchange rate (k) and half-life time (t(1/2)) examined by 2D EXSY NMR spectroscopy were found to be 0.209 +/- 0.013 s(-1) and 3.33 +/- 0.21 s, respectively. In contrast, the cis form of the azobenzene moiety required very long time (k = 2.14 +/- 0.27 x 10(-5) s(-1), t(1/2) = 9.13 +/- 1.2 h) to thread per-hydroxylated pillar[5]arene at 25 degrees C. Photoisomerization from the trans to the cis form generated the following increment of free energy of activation at 25 degrees C: Delta G(in)double dagger (cis form) - Delta G(in)double dagger(trans form) = 22.8 +/- 0.24 kJ mol(-1), which led to the time-scale transformation. The tuning of the threading was also accomplished by heating/cooling: the rate constants increased on heating and decreased on cooling.

  DOI：

  10.1021/jo202040p