(2R,6R)-2-Pentyl-1,8-diazaspiro<5,5>undecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (2R,6R)-2-Pentyl-1,8-diazaspiro<5,5>undecane
• 英文别名: (2R,6R)-2-pentyl-1,8-diazaspiro[5.5]undecane
• 化学式: C₁₄H₂₈N₂
• 分子量: 224.39
• InChiKey: XVAJXEQDVFFZDC-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.06
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (-)-2-氰-6-苯基恶唑哌啶 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 碳酸氢钠 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 52.5h， 生成 (2R,6R)-2-Pentyl-1,8-diazaspiro<5,5>undecane
  参考文献：
  名称：

  Asymmetric synthesis. 29. Preparation of 1,8-diazaspiro[5.5]undecane derivatives

  摘要：

  From 2-cyano-6-phenyl oxazolopiperidine 1, two highly efficient routes have been developed for the asymmetric synthesis of the spiropiperidine system: 1,8-diazaspiro[5.5]undecane. The key step was generation of the imine salts 6 and 17 from the functionalized alpha-amino nitrile 2, by nucleophilic addition of a suitable organometallic reagent to the nitrile group followed by, in situ, intramolecular nucleophilic alkylation. A reductive-cyclization procedure allowed the preparation of nonsubstituted and monosubstituted spiro compounds 5 and 10, respectively, while an alkylation-cyclization procedure led to the disubstituted spiro derivative 15, an aza analog of perhydrohistrionicotoxin.

  DOI：

  10.1021/jo00075a048

文献信息

• Asymmetric synthesis. 29. Preparation of 1,8-diazaspiro[5.5]undecane derivatives
  作者：Jieping Zhu、Jean Charles Quirion、Henri Philippe Husson

  DOI：10.1021/jo00075a048

  日期：1993.11

  From 2-cyano-6-phenyl oxazolopiperidine 1, two highly efficient routes have been developed for the asymmetric synthesis of the spiropiperidine system: 1,8-diazaspiro[5.5]undecane. The key step was generation of the imine salts 6 and 17 from the functionalized alpha-amino nitrile 2, by nucleophilic addition of a suitable organometallic reagent to the nitrile group followed by, in situ, intramolecular nucleophilic alkylation. A reductive-cyclization procedure allowed the preparation of nonsubstituted and monosubstituted spiro compounds 5 and 10, respectively, while an alkylation-cyclization procedure led to the disubstituted spiro derivative 15, an aza analog of perhydrohistrionicotoxin.