o-(diphenylphosphino)-N-((1R,2S)-1-hydroxy-1-phenyl-2-propyl)benzamide | 1175161-00-8

• 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: o-(diphenylphosphino)-N-((1R,2S)-1-hydroxy-1-phenyl-2-propyl)benzamide
• CAS: 1175161-00-8
• 化学式: C₂₈H₂₆NO₂P
• 分子量: 439.494
• InChiKey: GSDDIPDXCNTIHA-IDISGSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  o-(diphenylphosphino)-N-((1R,2S)-1-hydroxy-1-phenyl-2-propyl)benzamide 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到(1R,2S)-2-(2-(diphenylphosphinyl)benzamido)-1-phenylpropyl 4-nitrobenzoate
  参考文献：
  名称：

  Enantiomerically divergent pathways in Tsuji-Trost reactions: exploiting the structural differences between β-acyloxy-o-(diphenylphosphino)benzamides and β-amido-o-(diphenylphosphino)benzoates

  摘要：

  Using a single chiral scaffold, (1R,2S)-norephedrine, a series of monophosphine ligands have been prepared. The ligands prepared, beta-acyloxy-(o-diphenylphosphino)amides and beta-amido-(o-diphenylphosphino)esters, give rise to enantiomerically divergent products in the Tsuji-Trost asymmetric allylic reaction. The phosphinoamides afforded the best enantioselectivities and favored the (S)-enantiomer of the product. In contrast the phosphinoesters afforded lower enantioselectivities and favored the (R)-enantiomer. A mechanistic rationale for this observation is proposed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.012
• 作为产物：
  描述：

  去甲麻黄碱 、 2-二苯基膦苯甲酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到o-(diphenylphosphino)-N-((1R,2S)-1-hydroxy-1-phenyl-2-propyl)benzamide
  参考文献：
  名称：

  β-Hydroxy and β-(o-diphosphino)benzoyloxy(o-diphosphino) benzamides as ligands for asymmetric allylic alkylation

  摘要：

  Diphenylphosphinobenzoic acid was treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), DMAP, and with either one of two equivalents of (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine. This process yielded a series of beta-hydroxy and beta-(diphosphino) benzoyloxy(diphosphino)benzamides that were employed in the Tsuji-Trost asymmetric allylic alkylation process. It was determined that the diastereomeric geometry of the norephedrine series was superior to that of the pseudonorepliedrine-based ligands. In addition, it was determined that the norephedrine-based beta-(o-diphosphino)benzoyloxy(o-diphosphino)benzamide afforded the best enantiomeric ratio (94:6) favoring the (S)-enantiomer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.007
• 作为试剂：
  描述：

  1,3-二苯基-2-丙烯基乙酸酯 、 丙二酸二甲酯 在 N,O-双三甲硅基乙酰胺 、 bis(η3-allyl-μ-chloropalladium(II)) 、 o-(diphenylphosphino)-N-((1R,2S)-1-hydroxy-1-phenyl-2-propyl)benzamide 、 potassium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (R)-dimethyl 2-(1,3-diphenylallyl)malonate 、 (S)-dimethyl 2-(1,3-diphenylallyl)malonate
  参考文献：
  名称：

  β-Hydroxy and β-(o-diphosphino)benzoyloxy(o-diphosphino) benzamides as ligands for asymmetric allylic alkylation

  摘要：

  Diphenylphosphinobenzoic acid was treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), DMAP, and with either one of two equivalents of (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine. This process yielded a series of beta-hydroxy and beta-(diphosphino) benzoyloxy(diphosphino)benzamides that were employed in the Tsuji-Trost asymmetric allylic alkylation process. It was determined that the diastereomeric geometry of the norephedrine series was superior to that of the pseudonorepliedrine-based ligands. In addition, it was determined that the norephedrine-based beta-(o-diphosphino)benzoyloxy(o-diphosphino)benzamide afforded the best enantiomeric ratio (94:6) favoring the (S)-enantiomer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.007