7-benzyl-3-methoxy-3-borabicyclo[3.3.1]non-6-ene | 288577-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 7-benzyl-3-methoxy-3-borabicyclo[3.3.1]non-6-ene
• CAS: 288577-31-1
• 化学式: C₁₆H₂₁BO
• 分子量: 240.153
• InChiKey: RMHGAKCHBXLUIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-benzyl-3-methoxy-3-borabicyclo[3.3.1]non-6-ene 在 diborane(6) 作用下， 以 正戊烷 为溶剂， 反应 1.0h， 生成 2-phenyl-1-boraadamantane pyridine complex
  参考文献：
  名称：

  2-Phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics

  摘要：

  The reaction of triallylborane with 3-phenylprop-1-yne at 135-140 degrees C followed by treatment of the reaction mixture with MeOH afforded 7-benzyl-3-methoxy-3-borabicyclo[3.3. 1]non-6-ene (1) in 81% yield. Hydroboration of compound 1 with a solution of BH3 in THF yielded the tetrahydrofuran complex of 2-phenyl-1-boraadamantane (2). The reactions of trimethylamine or pyridine with compound 2 afforded the trimethylamine (3) or pyridine (4) complexes of 2-phenyl-1-boraadamantane, respectively. Hindered rotation about the C(2)-Ph bond in adduct 3 was observed by H-1 and C-13 NMR spectroscopy. The activation energy of this process is 58.6 kJ mol(-1) (determined by 2D H-1-H-1 EXSY spectroscopy).

  DOI：

  10.1007/bf02494783
• 作为产物：
  描述：

  三烯丙基硼烷 、 甲醇 、 3-苯-1-丙炔 反应 1.5h， 以81%的产率得到7-benzyl-3-methoxy-3-borabicyclo[3.3.1]non-6-ene
  参考文献：
  名称：

  2-Phenyl-1-boraadamantane complexes. Synthesis and intramolecular dynamics

  摘要：

  The reaction of triallylborane with 3-phenylprop-1-yne at 135-140 degrees C followed by treatment of the reaction mixture with MeOH afforded 7-benzyl-3-methoxy-3-borabicyclo[3.3. 1]non-6-ene (1) in 81% yield. Hydroboration of compound 1 with a solution of BH3 in THF yielded the tetrahydrofuran complex of 2-phenyl-1-boraadamantane (2). The reactions of trimethylamine or pyridine with compound 2 afforded the trimethylamine (3) or pyridine (4) complexes of 2-phenyl-1-boraadamantane, respectively. Hindered rotation about the C(2)-Ph bond in adduct 3 was observed by H-1 and C-13 NMR spectroscopy. The activation energy of this process is 58.6 kJ mol(-1) (determined by 2D H-1-H-1 EXSY spectroscopy).

  DOI：

  10.1007/bf02494783