1,3,5-tri(2-hydroxyphenyl)-2,4,6-trimethylbenzene | 1421368-52-6

• 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: 1,3,5-tri(2-hydroxyphenyl)-2,4,6-trimethylbenzene
• 英文别名: 2-[3,5-Bis(2-hydroxyphenyl)-2,4,6-trimethylphenyl]phenol；2-[3,5-bis(2-hydroxyphenyl)-2,4,6-trimethylphenyl]phenol
• CAS: 1421368-52-6
• 化学式: C₂₇H₂₄O₃
• 分子量: 396.486
• InChiKey: HPPFGWVVXSBWFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,5-tri(2-methoxyphenyl)-2,4,6-trimethylbenzene 在 水 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 1,3,5-tri(2-hydroxyphenyl)-2,4,6-trimethylbenzene
  参考文献：
  名称：

  Three Hydrogen Bond Donor Catalysts: Oxyanion Hole Mimics and Transition State Analogues

  摘要：

  Enzymes and their mimics use hydrogen bonds to catalyze chemical transformation's. Small molecule transition : state analogues of oxyanion holes have been characterized by computations, gas phase IR and photoelectron spectroscopy, and determination of their binding constants in acetonitrile. A new class of hydrogen bond catalysts is proposed (donors that can contribute three hydrogen bonds to a single functional group) and demonstrated in a Friedel-Crafts reaction. The employed catalyst was observed to react 100 times faster than its rotamer that can employ only two hydrogen bonds. The former compound also binds anions more tightly and was found to have a thermodynamic advantage.

  DOI：

  10.1021/ja3085862

文献信息

• Three Hydrogen Bond Donor Catalysts: Oxyanion Hole Mimics and Transition State Analogues
  作者：Evgeny V. Beletskiy、Jacob Schmidt、Xue-Bin Wang、Steven R. Kass

  DOI：10.1021/ja3085862

  日期：2012.11.14

  Enzymes and their mimics use hydrogen bonds to catalyze chemical transformation's. Small molecule transition : state analogues of oxyanion holes have been characterized by computations, gas phase IR and photoelectron spectroscopy, and determination of their binding constants in acetonitrile. A new class of hydrogen bond catalysts is proposed (donors that can contribute three hydrogen bonds to a single functional group) and demonstrated in a Friedel-Crafts reaction. The employed catalyst was observed to react 100 times faster than its rotamer that can employ only two hydrogen bonds. The former compound also binds anions more tightly and was found to have a thermodynamic advantage.