(3R,5S,8aR)-8a-[3-(1,3-dioxolan-2-yl)propyl]-5-(2-methoxyprop-2-enyl)-3-phenyl-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridine | 155267-00-8

• 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: (3R,5S,8aR)-8a-[3-(1,3-dioxolan-2-yl)propyl]-5-(2-methoxyprop-2-enyl)-3-phenyl-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridine
• CAS: 155267-00-8
• 化学式: C₂₃H₃₃NO₄
• 分子量: 387.519
• InChiKey: FYGBXONYWIJFDY-QNWVGRARSA-N

物化性质

• 沸点：
  492.9±40.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S,8aR)-8a-[3-(1,3-dioxolan-2-yl)propyl]-5-(2-methoxyprop-2-enyl)-3-phenyl-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以91%的产率得到(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-(3-氯丙基)-1,3-二噁戊环 、 Hexahydro-5-(2-methoxyprop-2-enyl)-3-phenyl-5H-oxazolo<3,2-a>pyridine 5-carbonitrile 在 叔丁基二甲硅基三氟甲磺酸酯 、 magnesium 作用下， 生成 (3R,5S,8aR)-8a-[3-(1,3-dioxolan-2-yl)propyl]-5-(2-methoxyprop-2-enyl)-3-phenyl-2,3,5,6,7,8-hexahydro-[1,3]oxazolo[3,2-a]pyridine 、 (1S,3S,9R)-3-(3-[1,3]Dioxolan-2-yl-propyl)-1-methoxy-9-phenyl-11-oxa-8-aza-tricyclo[5.4.1.0^3,8]dodecane
  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

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.