tert-butyl 4′-cyclopropyl-5′-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholine]-8-carboxylate

• 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: tert-butyl 4′-cyclopropyl-5′-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholine]-8-carboxylate
• 英文别名: Tert-butyl 4'-cyclopropyl-5'-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,2'-morpholine]-8-carboxylate；tert-butyl 4'-cyclopropyl-5'-oxospiro[8-azabicyclo[3.2.1]octane-3,2'-morpholine]-8-carboxylate
• 化学式: C₁₈H₂₈N₂O₄
• 分子量: 336.431
• InChiKey: HHSSULKGEVANRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4′-cyclopropyl-5′-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholine]-8-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以81%的产率得到4′-cyclopropyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-one hydrochloride
  参考文献：
  名称：

  Synthesis of 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones

  摘要：

  N-Boc-protected 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane] reacted with primary aliphatic amines through opening of the epoxide ring with formation of the corresponding amino alcohols which were converted into N-chloroacetyl derivatives. The latter underwent cyclization to N-Boc-protected 4'-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2'-morpholin]-5'-ones by the action of sodium hydride in DMF, and subsequent treatment with hydrogen chloride in ethyl acetate afforded 8-azaspiro[bicyclo[3.2.1]octane-3,2'-morpholin]-5'-one hydrochlorides.

  DOI：

  10.1134/s1070428016010164
• 作为产物：
  描述：

  tert-butyl 3-{[(2-chloro-1-oxoethyl)(cyclopropyl)-amino]methyl}-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 以77%的产率得到tert-butyl 4′-cyclopropyl-5′-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholine]-8-carboxylate
  参考文献：
  名称：

  Synthesis of 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones

  摘要：

  N-Boc-protected 8-azaspiro[bicyclo[3.2.1]octane-3,2'-oxirane] reacted with primary aliphatic amines through opening of the epoxide ring with formation of the corresponding amino alcohols which were converted into N-chloroacetyl derivatives. The latter underwent cyclization to N-Boc-protected 4'-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2'-morpholin]-5'-ones by the action of sodium hydride in DMF, and subsequent treatment with hydrogen chloride in ethyl acetate afforded 8-azaspiro[bicyclo[3.2.1]octane-3,2'-morpholin]-5'-one hydrochlorides.

  DOI：

  10.1134/s1070428016010164