(4S,5S)-2-diethylamino-4,5-diphenyl-1,3,2-dioxaphospholan | 146744-03-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5S)-2-diethylamino-4,5-diphenyl-1,3,2-dioxaphospholan
• 英文别名: (4S,5S)-N,N-diethyl-4,5-diphenyl-1,3,2-dioxaphospholan-2-amine
• CAS: 146744-03-8
• 化学式: C₁₈H₂₂NO₂P
• 分子量: 315.352
• InChiKey: UCGXFAOMFVPGFU-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S,S)-(-)-氢化苯偶姻 、 六乙基亚磷酸胺 反应 0.75h， 以69%的产率得到(4S,5S)-2-diethylamino-4,5-diphenyl-1,3,2-dioxaphospholan
  参考文献：
  名称：

  Phosphoramidites based on phenyl-substituted 1,2-diols as ligands in palladium-catalyzed asymmetric allylations: the contribution of steric demand and chiral centers to the enantioselectivity

  摘要：

  A small family of readily available phosphoramidite ligands, including compounds with P*-stereocenters, has been prepared from phenyl-substituted 1,2-diols as simple and cheap starting materials. Using these ligands, up to 84% ee was achieved in Pd-catalyzed asymmetric allylic substitution. The influence of structural modules such as asymmetric atoms and steric demand on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.122
• 作为试剂：
  描述：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 二正丙胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 (4S,5S)-2-diethylamino-4,5-diphenyl-1,3,2-dioxaphospholan 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (+)-(E)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine 、 (+)-(E)-1,3-diphenyl-N,N-dipropylprop-2-en-1-amine
  参考文献：
  名称：

  Phosphoramidites based on phenyl-substituted 1,2-diols as ligands in palladium-catalyzed asymmetric allylations: the contribution of steric demand and chiral centers to the enantioselectivity

  摘要：

  A small family of readily available phosphoramidite ligands, including compounds with P*-stereocenters, has been prepared from phenyl-substituted 1,2-diols as simple and cheap starting materials. Using these ligands, up to 84% ee was achieved in Pd-catalyzed asymmetric allylic substitution. The influence of structural modules such as asymmetric atoms and steric demand on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.122

文献信息

• Phosphoramidites based on phenyl-substituted 1,2-diols as ligands in palladium-catalyzed asymmetric allylations: the contribution of steric demand and chiral centers to the enantioselectivity
  作者：Konstantin N. Gavrilov、Sergey V. Zheglov、Mariya N. Gavrilova、Ilya V. Chuchelkin、Nikolay N. Groshkin、Eugenie A. Rastorguev、Vadim A. Davankov

  DOI：10.1016/j.tetlet.2011.08.122

  日期：2011.10

  A small family of readily available phosphoramidite ligands, including compounds with P*-stereocenters, has been prepared from phenyl-substituted 1,2-diols as simple and cheap starting materials. Using these ligands, up to 84% ee was achieved in Pd-catalyzed asymmetric allylic substitution. The influence of structural modules such as asymmetric atoms and steric demand on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.