(1S,2S)-2-(o-(diphenylphosphino)benzamido)-1-phenyl-propyl o-(diphenylphosphino)benzoate | 1175161-07-5

• 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: (1S,2S)-2-(o-(diphenylphosphino)benzamido)-1-phenyl-propyl o-(diphenylphosphino)benzoate
• 英文别名: [(1S,2S)-2-[(2-diphenylphosphanylbenzoyl)amino]-1-phenylpropyl] 2-diphenylphosphanylbenzoate
• CAS: 1175161-07-5
• 化学式: C₄₇H₃₉NO₃P₂
• 分子量: 727.779
• InChiKey: MAZMSMPPKYXBPZ-MAZBPMTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-二苯基膦苯甲酸 、 去甲伪麻黄碱 在 4-二甲氨基吡啶 、 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54%的产率得到(1S,2S)-2-(o-(diphenylphosphino)benzamido)-1-phenyl-propyl o-(diphenylphosphino)benzoate
  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

文献信息

• β-Hydroxy and β-(o-diphosphino)benzoyloxy(o-diphosphino) benzamides as ligands for asymmetric allylic alkylation
  作者：Geetanjali S. Mahadik、Stanley A. Knott、Lisa F. Szczepura、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2009.04.007

  日期：2009.6

  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.