(6R)-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: (6R)-1,8-Diazaspiro<5.5>undecane
• 英文别名: 1,8-Diazaspiro[5.5]undecane, (R)-(9CI)；(6R)-1,8-diazaspiro[5.5]undecane
• 化学式: C₉H₁₈N₂
• 分子量: 154.255
• InChiKey: FVIVALCKMXCKQX-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 12.5h， 生成 (6R)-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

• Macrocyclic Benzofused Pyrimidine Derivatives
  申请人：Altenbach Robert J.

  公开号：US20080188452A1

  公开（公告）日：2008-08-07

  Macrocyclic benzofused pyrimidine compounds, compositions comprising such compounds, methods for making the compounds, and methods of treating and preventing the progression of diseases, conditions and disorders using such compounds and compositions are described herein.

  本文描述了大环苯并嘧啶化合物、包含这种化合物的组合物、制备这种化合物的方法，以及使用这种化合物和组合物治疗和预防疾病、病症和障碍的方法。
• US8735411B2
  申请人：——

  公开号：US8735411B2

  公开（公告）日：2014-05-27
• 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.