[2-[[[4-[3-[[(2-Boronophenyl)methyl-methylamino]methyl]-2-methoxynaphthalen-1-yl]-3-methoxynaphthalen-2-yl]methyl-methylamino]methyl]phenyl]boronic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2-[[[4-[3-[[(2-Boronophenyl)methyl-methylamino]methyl]-2-methoxynaphthalen-1-yl]-3-methoxynaphthalen-2-yl]methyl-methylamino]methyl]phenyl]boronic acid
• 化学式: C₄₀H₄₂B₂N₂O₆
• 分子量: 668.405
• InChiKey: XCTMPEOVEFFGLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-甲酰基苯硼酸 、 (R)-2,2'-dimethoxy-n,N'-dimethyl-[1,1'-binaphthalene]-3,3'-dimethanamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以78%的产率得到[2-[[[4-[3-[[(2-Boronophenyl)methyl-methylamino]methyl]-2-methoxynaphthalen-1-yl]-3-methoxynaphthalen-2-yl]methyl-methylamino]methyl]phenyl]boronic acid
  参考文献：
  名称：

  Boronic Acid Receptors for α-Hydroxycarboxylates:  High Affinity of Shinkai's Glucose Receptor for Tartrate

  摘要：

  The glucose receptor I developed by Shinkai was synthesized by known methods and with modifications involving the final synthetic step, installation of the phenylboronic acid moieties. Binding of the bis(alpha-hydroxycarbolxylate), tartrate, was assessed and compared to the corresponding bis(diol), erythritol, as well as the corresponding mono(alpha-hydoxycarboxylate), malate. These results suggest that bisboronate/bis(alpha-hydoxycarboxylate) interactions are stronger than the corresponding bisboronate/bis(diol) interactions. Furthermore, we report that the receptor is an order of magnitude more selective for tartrate than malate.

  DOI：

  10.1021/jo025876y

文献信息

• Boronic Acid Receptors for α-Hydroxycarboxylates:  High Affinity of Shinkai's Glucose Receptor for Tartrate
  作者：Charles W. Gray、Todd A. Houston

  DOI：10.1021/jo025876y

  日期：2002.7.1

  The glucose receptor I developed by Shinkai was synthesized by known methods and with modifications involving the final synthetic step, installation of the phenylboronic acid moieties. Binding of the bis(alpha-hydroxycarbolxylate), tartrate, was assessed and compared to the corresponding bis(diol), erythritol, as well as the corresponding mono(alpha-hydoxycarboxylate), malate. These results suggest that bisboronate/bis(alpha-hydoxycarboxylate) interactions are stronger than the corresponding bisboronate/bis(diol) interactions. Furthermore, we report that the receptor is an order of magnitude more selective for tartrate than malate.
• Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar Acids
  作者：Jianzhang Zhao、Thomas M. Fyles、Tony D. James

  DOI：10.1002/anie.200454033

  日期：2004.6.28