(S)-2-(morpholin-4-ylmethyl)-pyrrolidine-1-carbonitrile | 890522-87-9

• 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: (S)-2-(morpholin-4-ylmethyl)-pyrrolidine-1-carbonitrile
• 英文别名: (2S)-2-(morpholin-4-ylmethyl)pyrrolidine-1-carbonitrile
• CAS: 890522-87-9
• 化学式: C₁₀H₁₇N₃O
• 分子量: 195.264
• InChiKey: MIZNTRHXYFQTGS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(morpholin-4-ylmethyl)-pyrrolidine-1-carbonitrile 、 (S)-4-(2-吡咯烷基甲基)吗啉 在 六氟异丙醇 作用下， 反应 16.0h， 以98.6%的产率得到C-[bis(2-(morpholin-4-ylmethyl)pyrrolidin-1-yl)]-methylenamine
  参考文献：
  名称：

  Synthesis of hindered chiral guanidine bases starting from (S)-(N,N-dialkyl-aminomethyl)pyrrolidines and BrCN

  摘要：

  An efficient method for the preparation of hindered chiral quanidines using cyanogen bromide is described. The reaction between BrCN and vicinal diamines derived from (S)-2-(N,N-dialkyl-amiilomethyl)-pyrrolidines provides chiral substituted cyanamides. The cyanamide derivatives reacted with secondary amines in hexafluoroisopropanol at reflux to form chiral hindered guanidines, which were isolated in good to excellent yields (70-96%). The chiral guanidines were prepared in an effort to design sophisticated chiral guanidine catalysts for asymmetric synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.009
• 作为产物：
  描述：

  溴化氰 、 (S)-4-(2-吡咯烷基甲基)吗啉 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到(S)-2-(morpholin-4-ylmethyl)-pyrrolidine-1-carbonitrile
  参考文献：
  名称：

  Synthesis of hindered chiral guanidine bases starting from (S)-(N,N-dialkyl-aminomethyl)pyrrolidines and BrCN

  摘要：

  An efficient method for the preparation of hindered chiral quanidines using cyanogen bromide is described. The reaction between BrCN and vicinal diamines derived from (S)-2-(N,N-dialkyl-amiilomethyl)-pyrrolidines provides chiral substituted cyanamides. The cyanamide derivatives reacted with secondary amines in hexafluoroisopropanol at reflux to form chiral hindered guanidines, which were isolated in good to excellent yields (70-96%). The chiral guanidines were prepared in an effort to design sophisticated chiral guanidine catalysts for asymmetric synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.009