1,2,2-triphenyl-1-tolylethanediol | 30332-88-8

• 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: 1,2,2-triphenyl-1-tolylethanediol
• 英文别名: 4-Methylbenzpinakol；1-(4-methylphenyl)-1,2,2-triphenylethane-1,2-diol
• CAS: 30332-88-8
• 化学式: C₂₇H₂₄O₂
• 分子量: 380.486
• InChiKey: CJCFPYZKWZYJQG-UHFFFAOYSA-N

物化性质

• 沸点：
  520.8±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,2,2-三苯乙酮 、 对甲苯基溴化镁 以 乙醚 为溶剂， 反应 2.0h， 生成 1,2,2-triphenyl-1-tolylethanediol
  参考文献：
  名称：

  Tetraarylethanediols: surprisingly low energy requirements for electron transfer in solution and in the gas phase

  摘要：

  A number of methyl-substituted tetraarylethanediols 1 have been found to undergo facile electron transfer (et) to tris(1,10-phenanthroline)iron(III) complexes (Fe(III)L3). The products of this reaction are the corresponding benzophenones when an appropriate base is added to the reaction solution. The electron-transfer rate constants (k(et)) for the reaction of 1 and Fe(III)L3 have been measured as a function of temperature and are higher than anticipated, based on the energetic predictions derived from model arenes. The oxidation potential, derived from the measured DELTA-G(et)*, is in good agreement with the solution-phase DELTA-G(et)-degrees, which can be calculated from the gas-phase ionization potential. Control experiments demonstrate that the reaction proceeds through a normal outer-sphere electron-transfer reaction. The surprisingly low oxidation potentials can only be explained by through-space phenyl-phenyl interactions.

  DOI：

  10.1021/ja00003a039