(3R,5R,8aR)-5-(3-hydroxypropyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile | 1026858-57-0

• 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: (3R,5R,8aR)-5-(3-hydroxypropyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS: 1026858-57-0
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: SZCRAYDDYUGSQL-GVDBMIGSSA-N

物化性质

• 沸点：
  467.7±40.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5R,8aR)-5-(3-hydroxypropyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile 在 四溴化碳 、 三苯基膦 作用下， 以 吡啶 为溶剂， 反应 0.5h， 以9.10 g的产率得到5-(3-bromopropyl)-3-phenylhexahydrooxazolo[3,2-a]pyridine-5-carbonitrile
  参考文献：
  名称：

  Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block

  摘要：

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

  DOI：

  10.1021/jo050258d
• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 、 3-溴-1-丙醇 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.33h， 生成 (3R,5R,8aR)-5-(3-hydroxypropyl)-3-phenyl-2,3,6,7,8,8a-hexahydro-[1,3]oxazolo[3,2-a]pyridine-5-carbonitrile
  参考文献：
  名称：

  Diasteroselective Synthesis of New Spiropiperidine Scaffolds from the CN(R,S) Building Block

  摘要：

  A methodology allowing the construction of spiropiperidine scaffolds similar to those found in naturally occurring alkaloids has been developed. This approach begins with the well-established CN(R,S) strategy, the spiro-center being built by way of an intramolecular attack of a nitrile function by an organolithium species obtained by a halogen/lithium exchange reaction mediated by either t-BuLi or lithium naphthalenide.

  DOI：

  10.1021/jo050258d