Hexahydro-5-acetonyl-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine | 141879-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Hexahydro-5-acetonyl-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine
• 英文别名: Hexahydro-5-acetonyl-8a-pentyl-3-phenyl-5H-oxazolo[3,2-a]pyridine
• CAS: 141879-11-0
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: XFHGWCZKNUOVMP-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Hexahydro-5-(2-methoxyprop-2-enyl)-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以90%的产率得到Hexahydro-5-acetonyl-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine
  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