Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo<3,2-a>pyridine 5-carbonitrile | 141848-08-0

• 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: Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo<3,2-a>pyridine 5-carbonitrile
• 英文别名: Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo[3,2-a]pyridine 5-carbonitrile；(3R,5R,8aR)-5-(2-methoxyprop-2-enyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 141848-08-0
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: GUGLQPFKUONMMG-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo<3,2-a>pyridine 5-carbonitrile 在 lithium aluminium tetrahydride 、 叔丁基二甲硅基三氟甲磺酸酯 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 8.67h， 生成 (2R)-2-[(2S,6S)-2-[3-(1,3-dioxolan-2-yl)propyl]-6-(2-methoxyprop-2-enyl)piperidin-1-yl]-2-phenylethanol
  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-甲氧基-3-溴丙烯 、 (-)-2-氰-6-苯基恶唑哌啶 在 lithium diisopropyl amide 作用下， 生成 Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo<3,2-a>pyridine 5-carbonitrile
  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

文献信息

• A new stereoselective synthesis of ladybug defense alkaloid precoccinelline
  作者：Chongwei Yue、Jean-François Nicolay、Jacques Royer、Henri-Philippe Husson

  DOI：10.1016/s0040-4020(01)81112-1

  日期：1994.3

  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.
• Asymmetric synthesis. 26. An expeditious enantioselective synthesis of the defense alkaloids (-)-euphococcinine and (-)-adaline via the CN(R,S) method
  作者：Chongwei Yue、Jacques Royer、Henri Philippe Husson

  DOI：10.1021/jo00041a028

  日期：1992.7

  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.