6-Benzyl-7-hydroxy-4,6-diazaspiro[2.4]heptan-5-one | 1012781-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 6-Benzyl-7-hydroxy-4,6-diazaspiro[2.4]heptan-5-one
• CAS: 1012781-86-0
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: XUHRTWPRLVPLRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Benzyl-7-hydroxy-4,6-diazaspiro[2.4]heptan-5-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到(1R,5S)-2-benzyl-2,4-diazabicyclo[3.2.0]heptan-3-one
  参考文献：
  名称：

  An unexpected aminocyclopropane reductive rearrangement

  摘要：

  A reductive rearrangement of aminocyclopropanes is described for the synthesis of cis- or trans-fused bicyclic 1,2-diaminocyclobutanes. Ionization of a cyclic aminal using BF(3)center dot OEt(2) induces rearrangement to a cyclobutyl iminium ion, which is subsequently reduced by Et(3)SiH. Substitution with allyltrimethylsilane allows carbon incorporation, giving a quaternary center. Silyloxy-substituted cyclopropanes rearrange rapidly to cyclobutanones which react with NaBH(4) to provide 1,2-aminohydroxycyclobutanes. These aminals were generated by the reduction of a Boc-imide with DIBAL-H or LiBH(4). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.054
• 作为产物：
  描述：

  6-Benzyl-4,6-diazaspiro[2.4]heptane-5,7-dione 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到6-Benzyl-7-hydroxy-4,6-diazaspiro[2.4]heptan-5-one
  参考文献：
  名称：

  An unexpected aminocyclopropane reductive rearrangement

  摘要：

  A reductive rearrangement of aminocyclopropanes is described for the synthesis of cis- or trans-fused bicyclic 1,2-diaminocyclobutanes. Ionization of a cyclic aminal using BF(3)center dot OEt(2) induces rearrangement to a cyclobutyl iminium ion, which is subsequently reduced by Et(3)SiH. Substitution with allyltrimethylsilane allows carbon incorporation, giving a quaternary center. Silyloxy-substituted cyclopropanes rearrange rapidly to cyclobutanones which react with NaBH(4) to provide 1,2-aminohydroxycyclobutanes. These aminals were generated by the reduction of a Boc-imide with DIBAL-H or LiBH(4). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.054