(pS)-2-(1-naphthyl)-1-(B(OH)OMe) ferrocene | 1350900-12-7

• 英文名称: (pS)-2-(1-naphthyl)-1-(B(OH)OMe) ferrocene
• CAS: 1350900-12-7
• 化学式: C₂₁H₁₉BFeO₂
• 分子量: 370.039
• InChiKey: WPJJQHDFGYSZHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (pS)-2-(1-naphthyl)-1-(B(OH)OMe) ferrocene 以 氯仿 为溶剂， 以78%的产率得到[(pS)-2-(1-naphthyl)-1-(BO) ferrocene]3
  参考文献：
  名称：

  Reversible Formation of a Planar Chiral Ferrocenylboroxine and Its Supramolecular Structure

  摘要：

  The boronic acid (pS)-1,2-NpFcB(OH)(2) (1) was obtained by treatment of the lithiated species (pS)-1,2-NpFcLi with B((OPr)-Pr-i)(3), followed by acidic workup; subsequent dehydration gave the enantiomerically pure boroxine [(pS)-1,2-NpFcBO](3) (2) in 49% isolated yield. Multinuclear and 2D NMR spectroscopies, single-crystal X-ray diffraction, and elemental analysis served to confirm the structure of 2. In the solid-state structure, all three of the naphthyl groups point in one direction and all of the ferrocenyl moieties are placed on the opposite face of the boroxine ring, which is also the preferred conformation in solution according to a H-1, H-1-NOESY experiment. Cyclic voltammetry revealed three separate reversible oxidation events, which suggests significant communication between the ferrocenyl moieties. These redox processes experience a cathodic shift upon addition of 4-dimethylaminopyridine (DMAP) as a Lewis base. The six-membered ring is opened upon treatment with hot CHCl3/MeOH to form the methoxy species (pS)-1,2-NpFcB(OH)(OMe) (3), which can be converted back to the cycle 2 by dissolution in wet CHCl3, followed by column chromatography on silica gel.

  DOI：

  10.1021/om200947v
• 作为产物：
  描述：

  甲醇 、 [(pS)-2-(1-naphthyl)-1-(BO) ferrocene]3*2(chloroform) 以 甲醇 、 氯仿 、 水 为溶剂， 以81%的产率得到(pS)-2-(1-naphthyl)-1-(B(OH)OMe) ferrocene
  参考文献：
  名称：

  Reversible Formation of a Planar Chiral Ferrocenylboroxine and Its Supramolecular Structure

  摘要：

  The boronic acid (pS)-1,2-NpFcB(OH)(2) (1) was obtained by treatment of the lithiated species (pS)-1,2-NpFcLi with B((OPr)-Pr-i)(3), followed by acidic workup; subsequent dehydration gave the enantiomerically pure boroxine [(pS)-1,2-NpFcBO](3) (2) in 49% isolated yield. Multinuclear and 2D NMR spectroscopies, single-crystal X-ray diffraction, and elemental analysis served to confirm the structure of 2. In the solid-state structure, all three of the naphthyl groups point in one direction and all of the ferrocenyl moieties are placed on the opposite face of the boroxine ring, which is also the preferred conformation in solution according to a H-1, H-1-NOESY experiment. Cyclic voltammetry revealed three separate reversible oxidation events, which suggests significant communication between the ferrocenyl moieties. These redox processes experience a cathodic shift upon addition of 4-dimethylaminopyridine (DMAP) as a Lewis base. The six-membered ring is opened upon treatment with hot CHCl3/MeOH to form the methoxy species (pS)-1,2-NpFcB(OH)(OMe) (3), which can be converted back to the cycle 2 by dissolution in wet CHCl3, followed by column chromatography on silica gel.

  DOI：

  10.1021/om200947v