(S)-2-(anilinodiphenylmethyl)pyrrolidine | 1421699-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(anilinodiphenylmethyl)pyrrolidine
• 英文别名: N-[diphenyl-[(2S)-pyrrolidin-2-yl]methyl]aniline
• CAS: 1421699-01-5
• 化学式: C₂₃H₂₄N₂
• 分子量: 328.457
• InChiKey: JSCVBKULYUTANJ-QFIPXVFZSA-N

物化性质

• 沸点：
  475.0±35.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzyl-(S)-proline methyl ester 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium azide 、 硫酸 、 palladium on activated charcoal 、 水 、 氢气 、 cesium acetate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 102.0h， 生成 (S)-2-(anilinodiphenylmethyl)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：

  alpha-氯乙酰苯 在 dimethyl sulfide borane 、 (S)-2-(anilinodiphenylmethyl)pyrrolidine 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(R)-(-)-2-氯-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

文献信息

• Synthesis of chiral 2-(anilinophenylmethyl)pyrrolidines and 2-(anilinodiphenylmethyl)pyrrolidine and their application to enantioselective borane reduction of prochiral ketones as chiral catalysts
  作者：Naoya Hosoda、Hideaki Kamito、Miki Takano、Yoshitaka Takebe、Yoshitaka Yamaguchi、Masatoshi Asami

  DOI：10.1016/j.tet.2012.12.024

  日期：2013.2

  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.