Hexahydro-5-(2-methoxyprop-2-enyl)-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine | 141848-12-6

• 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-(2-methoxyprop-2-enyl)-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine
• 英文别名: Hexahydro-5-(2-methoxyprop-2-enyl)-8a-pentyl-3-phenyl-5H-oxazolo[3,2-a]pyridine
• CAS: 141848-12-6
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: VWDWVYFLYFKZEI-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  Hexahydro-5-(2-methoxyprop-2-enyl)-8a-pentyl-3-phenyl-5H-oxazolo<3,2-a>pyridine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以93%的产率得到(R)-2-[(2R,6R)-2-(2-Methoxy-allyl)-6-pentyl-piperidin-1-yl]-2-phenyl-ethanol
  参考文献：
  名称：

  A new stereoselective synthesis of ladybug defense alkaloid precoccinelline

  摘要：

  We have accomplished a new stereoselective synthesis of precoccinelline 1 in six steps from the chiral synthon 6 with a overall yield of 31 %. The main feature of this synthesis is the asymmetric synthesis of the trans 2,6-keto-acetal piperidine 14 which assures a stereospecific cyclisation in the construction of key intermediate ketone 4.

  DOI：

  10.1016/s0040-4020(01)81112-1
• 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 Hexahydro-5-(2-methoxyprop-2-enyl)-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