(2R,1'R)-2-(anilinophenylmethyl)pyrrolidine | 1421699-00-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R,1'R)-2-(anilinophenylmethyl)pyrrolidine
• 英文别名: N-[(R)-phenyl-[(2R)-pyrrolidin-2-yl]methyl]aniline
• CAS: 1421699-00-4
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: LTKVWMIITUSYAL-IAGOWNOFSA-N

物化性质

• 沸点：
  395.4±17.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,1'R)-2-(anilinophenylmethyl)pyrrolidine 在 正丁基锂 、 sodium hydroxide 作用下， 生成 1,2-diphenylhexahydro-3H-pyrrolo[1,2-c]imidazol-3-one
  参考文献：
  名称：

  Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts

  摘要：

  Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl)pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.024
• 作为产物：
  描述：

  (4R,5R)-3,4-diphenyl-1,3-diazabicyclo[3.3.0]octane 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以40%的产率得到(2R,1'R)-2-(anilinophenylmethyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts

  摘要：

  Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl)pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.024
• 作为试剂：
  描述：

  苯乙酮 在 硼烷二甲硫醚络合物 、 (2R,1'R)-2-(anilinophenylmethyl)pyrrolidine 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到(S)-(-)-1-苯乙醇
  参考文献：
  名称：

  Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts

  摘要：

  Chiral diamines, 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine, were prepared from N-(tert-butoxycarbonyl)pyrrolidine or (S)-proline as a starting material, respectively. These chiral diamines were efficient for the catalytic enantioselective borane reduction of acetophenone. Using (S)-2-(anilinodiphenylmethyl)pyrrolidine, chiral secondary alcohols were obtained from prochiral ketones with good to excellent enantiomeric excesses (up to 98% ee). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.024