ethyl 1α,5α,6α-6-morpholino-3-azabicyclo<3.1.0>hexane-3-carboxylate | 138457-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: ethyl 1α,5α,6α-6-morpholino-3-azabicyclo<3.1.0>hexane-3-carboxylate
• CAS: 138457-61-1
• 化学式: C₁₂H₂₀N₂O₃
• 分子量: 240.302
• InChiKey: XWZQYXXTCRKKSF-URLYPYJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1α,5α,6α-6-morpholino-3-azabicyclo<3.1.0>hexane-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 40.0h， 以84%的产率得到4-(1α,5α,6α-3-methyl-3-azabicyclo[3.1.0]hex-6-yl)-morpholine
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - viii. Amino-azabicyclo[3.1.0]hexane diastereomers from chloroenamines and - borohydride

  摘要：

  Bicyclic endo-amines 6a,b could be prepared in a stereospecific way from the reaction of chloroenamines 1a,b and sodium borohydride and by deboranation of the primarily formed borane adducts 8. An X-ray structure analysis is given for 8a. In contrast to 1a,b, chloroenamine 1c and sodium borohydride preferentially produced an exo-amine 7c besides the endo-amine 6c (3:1). Subsequent LiAlH4-reduction of 7c allowed the synthesis of 7a - the diastereoisomer of 6a. Interaction of sodium borohydride with dichloroenamine 2a provided diamine 12 instead of an expected bicyclic exo-amine 10.

  DOI：

  10.1016/s0040-4020(01)91008-7
• 作为产物：
  描述：

  3-Chloro-4-morpholin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 72.0h， 以23%的产率得到ethyl 1α,5α,6β-6-morpholino-3-azabicyclo<3.1.0>hexane-3-carboxylate
  参考文献：
  名称：

  Functionalized chloroenamines in aminocyclopropane synthesis - viii. Amino-azabicyclo[3.1.0]hexane diastereomers from chloroenamines and - borohydride

  摘要：

  Bicyclic endo-amines 6a,b could be prepared in a stereospecific way from the reaction of chloroenamines 1a,b and sodium borohydride and by deboranation of the primarily formed borane adducts 8. An X-ray structure analysis is given for 8a. In contrast to 1a,b, chloroenamine 1c and sodium borohydride preferentially produced an exo-amine 7c besides the endo-amine 6c (3:1). Subsequent LiAlH4-reduction of 7c allowed the synthesis of 7a - the diastereoisomer of 6a. Interaction of sodium borohydride with dichloroenamine 2a provided diamine 12 instead of an expected bicyclic exo-amine 10.

  DOI：

  10.1016/s0040-4020(01)91008-7