(2S,3R,4R,5S)-3-benzylamino-1,5-dimethyl-2,4-diphenyl-pyrrolidine | 873668-90-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3R,4R,5S)-3-benzylamino-1,5-dimethyl-2,4-diphenyl-pyrrolidine
• 英文别名: (2S,3R,4R,5S)-N-benzyl-1,5-dimethyl-2,4-diphenylpyrrolidin-3-amine
• CAS: 873668-90-7
• 化学式: C₂₅H₂₈N₂
• 分子量: 356.511
• InChiKey: XMZQTXKDICFYAJ-KTEAYJLESA-N

物化性质

• 沸点：
  489.8±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S)-3-benzylamino-1,5-dimethyl-2,4-diphenyl-pyrrolidine 、 二碳酸二叔丁酯 以 乙酸乙酯 为溶剂， 反应 2.0h， 以79%的产率得到(2S,3R,4R,5S)-3-(N-tert-butoxycarbonyl-benzylamino)-1,5-dimethyl-2,4-diphenyl-pyrrolidine
  参考文献：
  名称：

  3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline

  摘要：

  [GRAPHICS]A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.

  DOI：

  10.1021/ol052388e
• 作为产物：
  描述：

  (2S,3S,4S)-1,4-dimethyl-3-phenyl-azetidine-2-carbonitrile 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 5.25h， 生成 (2S,3R,4R,5S)-3-benzylamino-1,5-dimethyl-2,4-diphenyl-pyrrolidine
  参考文献：
  名称：

  3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline

  摘要：

  [GRAPHICS]A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.

  DOI：

  10.1021/ol052388e

文献信息

• 3-Aminopyrrolidines via Ring Rearrangement of 2-Aminomethylazetidines. Synthesis of (−)-Absouline
  作者：Monica Vargas-Sanchez、François Couty、Gwilherm Evano、Damien Prim、Jérome Marrot

  DOI：10.1021/ol052388e

  日期：2005.12.1

  [GRAPHICS]A new entry to enantiopure 3-aminopyrrolidines was developed using a boron trifluoride-mediated rearrangement of 2-aminomethylazetidines. The method is quite general and produces rearranged products in good yield regardless of both substitution pattern and relative stereochemistry of the starting material. A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method.