(5S)-2-diethylamino-4,4,5-triphenyl-1,3,2-dioxaphospholane | 1341180-97-9

• 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: (5S)-2-diethylamino-4,4,5-triphenyl-1,3,2-dioxaphospholane
• 英文别名: (5S)-2-diethylamino-4,4,5-triphenyl-1,3,2-dioxaphospholan；(5S)-N,N-diethyl-4,4,5-triphenyl-1,3,2-dioxaphospholan-2-amine
• CAS: 1341180-97-9
• 化学式: C₂₄H₂₆NO₂P
• 分子量: 391.45
• InChiKey: XRXZUFGHTQOCCI-UHFKCPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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)-(-)-1,1,2-三苯基-1,2-乙二醇 、 六乙基亚磷酸胺 以 甲苯 为溶剂， 反应 2.0h， 以65%的产率得到(5S)-2-diethylamino-4,4,5-triphenyl-1,3,2-dioxaphospholane
  参考文献：
  名称：

  Chiral 1,3,2-dioxaphospholane amidophosphite in the palladium-catalyzed enantioselective allylation

  摘要：

  将(S)-1,1,2-三苯基乙烷-1,2-二醇磷酸化可得到环状 P* 手性氨基亚磷酸酯，将其作为配体应用于 1,3-二苯基乙酸烯丙基酯的 Pd 催化烯丙基取代反应中，可提供高达 70% 的产品 ee。

  DOI：

  10.1007/s11172-011-0326-1
• 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)) 、 (5S)-2-diethylamino-4,4,5-triphenyl-1,3,2-dioxaphospholane 作用下， 以 二氯甲烷 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

• Chiral 1,3,2-dioxaphospholane amidophosphite in the palladium-catalyzed enantioselective allylation
  作者：K. N. Gavrilov、I. V. Chuchelkin、S. V. Zheglov、M. N. Gavrilova、E. A. Rastorguev、V. A. Davankov

  DOI：10.1007/s11172-011-0326-1

  日期：2011.10

  Phosphorylation of (S)-1,1,2-triphenylethane-1,2-diol furnishes cyclic P*-chiral amidophosphite, whose application as a ligand in the Pd-catalyzed allyl substitution in 1,3-diphenylallyl acetate provides the products ee up to 70%.

  将(S)-1,1,2-三苯基乙烷-1,2-二醇磷酸化可得到环状 P* 手性氨基亚磷酸酯，将其作为配体应用于 1,3-二苯基乙酸烯丙基酯的 Pd 催化烯丙基取代反应中，可提供高达 70% 的产品 ee。
• 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.