1-Aza-2-phenyl-4-oxa-5-methoxy-7-pentyltricyclo<5.4.15,11.0>dodecane | 141848-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Aza-2-phenyl-4-oxa-5-methoxy-7-pentyltricyclo<5.4.15,11.0>dodecane
• 英文别名: 1-Aza-2-phenyl-4-oxa-5-methoxy-7-pentyltricyclo<5.4.1^5,11.0>dodecane
• CAS: 141848-10-4
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: MLJXIBHTKBZYDK-MBDNFAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Aza-2-phenyl-4-oxa-5-methoxy-7-pentyltricyclo<5.4.15,11.0>dodecane 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以76%的产率得到(-)-adaline
  参考文献：
  名称：

  Asymmetric synthesis. 26. An expeditious enantioselective synthesis of the defense alkaloids (-)-euphococcinine and (-)-adaline via the CN(R,S) method

  摘要：

  The unnatural enantiomer (-)-euphococcinine (2) and the natural enantiomer of (-)-adaline (3), two homotropane alkaloids, were each prepared in three steps from chiral (-)-2-cyano-6-oxazolopiperidine synthon 8 by the CN(R,S) method. The key steps of these syntheses are the formation of a chiral quaternary center alpha to the piperidine nitrogen with complete stereocontrol and a subsequent intramolecular Mannich reaction. The previously unknown absolute configuration of natural (+)-euphococcinine was deduced from the synthesis of its enantiomer (-)-2.

  DOI：

  10.1021/jo00041a028
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 叔丁基二甲硅基三氟甲磺酸酯 、 lithium diisopropyl amide 作用下， 反应 3.67h， 生成 1-Aza-2-phenyl-4-oxa-5-methoxy-7-pentyltricyclo<5.4.15,11.0>dodecane
  参考文献：
  名称：

  Asymmetric synthesis. 26. An expeditious enantioselective synthesis of the defense alkaloids (-)-euphococcinine and (-)-adaline via the CN(R,S) method

  摘要：

  The unnatural enantiomer (-)-euphococcinine (2) and the natural enantiomer of (-)-adaline (3), two homotropane alkaloids, were each prepared in three steps from chiral (-)-2-cyano-6-oxazolopiperidine synthon 8 by the CN(R,S) method. The key steps of these syntheses are the formation of a chiral quaternary center alpha to the piperidine nitrogen with complete stereocontrol and a subsequent intramolecular Mannich reaction. The previously unknown absolute configuration of natural (+)-euphococcinine was deduced from the synthesis of its enantiomer (-)-2.

  DOI：

  10.1021/jo00041a028