(4-(1-Hydroxy-2-methylpropan-2-yl)phenyl)boronic acid | 1310707-18-6

• 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: (4-(1-Hydroxy-2-methylpropan-2-yl)phenyl)boronic acid
• 英文别名: [4-(1-hydroxy-2-methylpropan-2-yl)phenyl]boronic acid
• CAS: 1310707-18-6
• 化学式: C₁₀H₁₅BO₃
• 分子量: 194.038
• InChiKey: MULKEWTUFWXSGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  硼酸三甲酯 、 2-(4-溴苯基)-2-甲基丙烷-1-醇 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (4-(1-Hydroxy-2-methylpropan-2-yl)phenyl)boronic acid
  参考文献：
  名称：

  Metabolically Stable tert-Butyl Replacement

  摘要：

  Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.

  DOI：

  10.1021/ml400045j

文献信息

• Metabolically Stable <i>tert</i>-Butyl Replacement
  作者：David Barnes-Seeman、Monish Jain、Leslie Bell、Suzie Ferreira、Scott Cohen、Xiao-Hui Chen、Jakal Amin、Brad Snodgrass、Panos Hatsis

  DOI：10.1021/ml400045j

  日期：2013.6.13

  Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.