2-((3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-((3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)quinoline
• 英文别名: 2-[(3,3-Dimethyl-2-bicyclo[2.2.1]heptanyl)methyl]quinoline；2-[(3,3-dimethyl-2-bicyclo[2.2.1]heptanyl)methyl]quinoline
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: CBTLDRLDRYHUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  喹啉 、 莰烯 在 [(cod)₂RhCl]₂ tricyclohexylphosphonium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以90%的产率得到2-((3,3-dimethylbicyclo[2.2.1]heptan-2-yl)methyl)quinoline
  参考文献：
  名称：

  Rh(I)-Catalyzed Alkylation of Quinolines and Pyridines via C−H Bond Activation

  摘要：

  The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work.

  DOI：

  10.1021/ja070388z

文献信息

• Rh(I)-Catalyzed Alkylation of Quinolines and Pyridines via C−H Bond Activation
  作者：Jared C. Lewis、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja070388z

  日期：2007.5.1

  The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work.