(1S,3S,4S)-3-(4-chlorophenylamino)spiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-5-one | 1169830-66-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,3S,4S)-3-(4-chlorophenylamino)spiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-5-one
• 英文别名: (1S,4S,6S)-6-(4-chloroanilino)spiro[bicyclo[2.2.2]octane-5,1'-cyclohexane]-2-one
• CAS: 1169830-66-3
• 化学式: C₁₉H₂₄ClNO
• 分子量: 317.859
• InChiKey: ABOBURMHQPVOIM-XCRHUMRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 (4-Chloro-phenyl)-[1-cyclohexyl-meth-(E)-ylidene]-amine 在 (S)-N-(4-十二烷基苯磺酰基)吡咯烷-2-甲酰胺 作用下， 反应 48.0h， 生成 (1R,3R,4R)-3-(4-chlorophenylamino)spiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-5-one 、 (1S,3S,4S)-3-(4-chlorophenylamino)spiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-5-one
  参考文献：
  名称：

  Asymmetric Construction of Nitrogen-Containing [2.2.2] Bicyclic Scaffolds Using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide

  摘要：

  An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.

  DOI：

  10.1021/jo9009062