[4-[[(3,5-Ditert-butylphenyl)methylamino]methyl]phenyl]methanol | 216966-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-[[(3,5-Ditert-butylphenyl)methylamino]methyl]phenyl]methanol
• 英文别名: [4-[[(3,5-ditert-butylphenyl)methylamino]methyl]phenyl]methanol
• CAS: 216966-20-0
• 化学式: C₂₃H₃₃NO
• 分子量: 339.521
• InChiKey: RPGAUPWFQJSPLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-[[(3,5-Ditert-butylphenyl)methylamino]methyl]phenyl]methanol 在 盐酸 、 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Acid−Base Controllable Molecular Shuttles

  摘要：

  Two novel [2]rotananes, comprised of a dibenzo[24]crown-8 (DB24C8) macroring bound mechanically to a chemical "dumbbell" possessing two different recognition sites-viz., secondary dialkylammonium (NH2+) and 4,4'-bipyridinium (Bpym(2+)) units-have been synthesized by using the supramolecular assistance to synthesis provided by, inter alia, hydrogen bonding interactions. One of these rotaxanes bears a fluorescent and redox-active anthracene (Anth) stopper unit. NMR spectroscopy and X-ray crystallography have demonstrated that the DB24C8 macroring exhibits complete selectivity for the NH2+ recognition sites, i.e., that the [2]rotaxanes exist as only one of two possible translational isomers. Deprotonation of the rotaxanes' NH2+ centers effects a quantitative displacement of the DB24C8 macroring to the Bpym(2+) recognition site, an outcome that can be reversed by acid treatment. The switching processes have been investigated by H-1 NMR spectroscopy and, for the Anth-bearing rotaxane, by electrochemical and photophysical measurements. Furthermore, it is possible to drive the DB24C8 macroring from the dumbbell's Bpym(2+) unit, in the deprotonated form of the Anth-bearing rotaxane, by destroying the stabilizing DB24C8-Bpym(2+) charge-transfer interactions via electrochemical reduction. The photochemical and photophysical properties of this rotaxane (in both its protonated and deprotonated states) have also been investigated.

  DOI：

  10.1021/ja982167m
• 作为产物：
  描述：

  3,5-双(叔丁基)苯甲醛 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 生成 [4-[[(3,5-Ditert-butylphenyl)methylamino]methyl]phenyl]methanol
  参考文献：
  名称：

  The Self-Assembly of a Switchable[2]Rotaxane

  摘要：

  DOI：

  10.1002/anie.199719041

文献信息

• The Self-Assembly of a Switchable[2]Rotaxane
  作者：M.-Victoria Martínez-Díaz、Neil Spencer、J. Fraser Stoddart

  DOI：10.1002/anie.199719041

  日期：1997.9.17
• Acid−Base Controllable Molecular Shuttles
  作者：Peter R. Ashton、Roberto Ballardini、Vincenzo Balzani、Ian Baxter、Alberto Credi、Matthew C. T. Fyfe、Maria Teresa Gandolfi、Marcos Gómez-López、M.-Victoria Martínez-Díaz、Arianna Piersanti、Neil Spencer、J. Fraser Stoddart、Margherita Venturi、Andrew J. P. White、David J. Williams

  DOI：10.1021/ja982167m

  日期：1998.11.1

  Two novel [2]rotananes, comprised of a dibenzo[24]crown-8 (DB24C8) macroring bound mechanically to a chemical "dumbbell" possessing two different recognition sites-viz., secondary dialkylammonium (NH2+) and 4,4'-bipyridinium (Bpym(2+)) units-have been synthesized by using the supramolecular assistance to synthesis provided by, inter alia, hydrogen bonding interactions. One of these rotaxanes bears a fluorescent and redox-active anthracene (Anth) stopper unit. NMR spectroscopy and X-ray crystallography have demonstrated that the DB24C8 macroring exhibits complete selectivity for the NH2+ recognition sites, i.e., that the [2]rotaxanes exist as only one of two possible translational isomers. Deprotonation of the rotaxanes' NH2+ centers effects a quantitative displacement of the DB24C8 macroring to the Bpym(2+) recognition site, an outcome that can be reversed by acid treatment. The switching processes have been investigated by H-1 NMR spectroscopy and, for the Anth-bearing rotaxane, by electrochemical and photophysical measurements. Furthermore, it is possible to drive the DB24C8 macroring from the dumbbell's Bpym(2+) unit, in the deprotonated form of the Anth-bearing rotaxane, by destroying the stabilizing DB24C8-Bpym(2+) charge-transfer interactions via electrochemical reduction. The photochemical and photophysical properties of this rotaxane (in both its protonated and deprotonated states) have also been investigated.