1,1'-(diphenylamine-2,2'-dicarbonyl)-bis[(2S)-α,α-diphenyl-2-pyrrolidinemethanol] | 1164109-69-6

• 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: 1,1'-(diphenylamine-2,2'-dicarbonyl)-bis[(2S)-α,α-diphenyl-2-pyrrolidinemethanol]
• 英文别名: [2-[2-[(2S)-2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carbonyl]anilino]phenyl]-[(2S)-2-[hydroxy(diphenyl)methyl]pyrrolidin-1-yl]methanone
• CAS: 1164109-69-6
• 化学式: C₄₈H₄₅N₃O₄
• 分子量: 727.903
• InChiKey: RREJSIWKSHTQDK-CXNSMIOJSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  905.3±65.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-(+)-alpha,alpha-二苯基脯氨醇 、 2,2'-iminodibenzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以5.82 g的产率得到1,1'-(diphenylamine-2,2'-dicarbonyl)-bis[(2S)-α,α-diphenyl-2-pyrrolidinemethanol]
  参考文献：
  名称：

  Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones

  摘要：

  A series of bis-hydroxyamides were synthesized from diphenylamine-2,2'-dicarboxylic acid and chiral aminoalcohols. Their catalytic activity in asymmetric borane reduction was investigated. After the fine optimization of solvents, temperature, amount of borane complex, and the length of catalyst generating period, good to excellent yields (55-99%) and enantioselectivities (79-97% ee) can be achieved in the reduction of aromatic and alkyl prochiral ketones. A transition state structure was proposed on the basis of absolute configuration and controlled experiment. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.057
• 作为试剂：
  描述：

  硫代异氰酸苯酯 、 乙酰基环己烷 在 硼烷四氢呋喃络合物 、 1,1'-(diphenylamine-2,2'-dicarbonyl)-bis[(2S)-α,α-diphenyl-2-pyrrolidinemethanol] 、 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 生成 、 (R)-O-(1-cyclohexylethyl) phenylcarbamothioate
  参考文献：
  名称：

  Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones

  摘要：

  A series of bis-hydroxyamides were synthesized from diphenylamine-2,2'-dicarboxylic acid and chiral aminoalcohols. Their catalytic activity in asymmetric borane reduction was investigated. After the fine optimization of solvents, temperature, amount of borane complex, and the length of catalyst generating period, good to excellent yields (55-99%) and enantioselectivities (79-97% ee) can be achieved in the reduction of aromatic and alkyl prochiral ketones. A transition state structure was proposed on the basis of absolute configuration and controlled experiment. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.057

文献信息

• Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones
  作者：Jin Wang、Han Liu、Da-Ming Du

  DOI：10.1016/j.tetasy.2009.02.057

  日期：2009.3

  A series of bis-hydroxyamides were synthesized from diphenylamine-2,2'-dicarboxylic acid and chiral aminoalcohols. Their catalytic activity in asymmetric borane reduction was investigated. After the fine optimization of solvents, temperature, amount of borane complex, and the length of catalyst generating period, good to excellent yields (55-99%) and enantioselectivities (79-97% ee) can be achieved in the reduction of aromatic and alkyl prochiral ketones. A transition state structure was proposed on the basis of absolute configuration and controlled experiment. (C) 2009 Elsevier Ltd. All rights reserved.