4-(1α,5α,6α-3-methyl-3-azabicyclo[3.1.0]hex-6-yl)-morpholine | 138457-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(1α,5α,6α-3-methyl-3-azabicyclo[3.1.0]hex-6-yl)-morpholine
• CAS: 138457-62-2
• 化学式: C₁₀H₁₈N₂O
• 分子量: 182.266
• InChiKey: YQKZKPLTYNLWJV-MYJAWHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.71
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 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 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 水 为溶剂， 反应 112.0h， 生成 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

文献信息

• Reductive Decyanation of Annulated Aminocyclopropane-endo-carbonitriles - a way to annulated cyclopropane-exo-amines
  作者：Elmar Vilsmaier、Gunther Milch、Wolfgang Roth、Walter Frank、Guido Rei�

  DOI：10.1002/prac.19983400410

  日期：——

  Annulated Aminocyclopropane-endo-carbonitriles 11a,b are reductively decyanated by sodium in liquid ammonia with complete retention of configuration. An additionally existing chlorine atom in the starting materials 12a,c-e, thereby, is simultaneously replaced by hydrogen. The preparative advantage of this method is demonstrated by the selective access to 6 alpha-H-isomers 13b and 13e as members of the ensemble of bicyclo[3.1.0]hexanediyl-dimorpholine diastereomers. A strong buckled bicyclohexane unit is present in 3 alpha,6 alpha-isomer 13e as indicated by H-1 NMR spectroscopy and X-ray structural analysis.