2,2'-bis((2R,5R)-2,5-dimethylphospholan-1-yloxy)-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-bis((2R,5R)-2,5-dimethylphospholan-1-yloxy)-1,1'-binaphthyl
• 英文别名: (2R,5R)-1-[1-[2-[(2R,5R)-2,5-dimethylphospholan-1-yl]oxynaphthalen-1-yl]naphthalen-2-yl]oxy-2,5-dimethylphospholane
• 化学式: C₃₂H₃₆O₂P₂
• 分子量: 514.584
• InChiKey: DKKOWZSRUIQCPW-MOUTVQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R,R)-2,5-dimethyl-1-(trimethylsilyl)phospholane 在 六氯乙烷 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2,2'-bis((2R,5R)-2,5-dimethylphospholan-1-yloxy)-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of Binol-based diphosphinites bearing chiral phospholane units and their application in asymmetric catalysis

  摘要：

  New diphosphinite ligands based on atropoisomeric diol backbones and (R,R)-2,5-dimethylphospholane moieties have been prepared and fully characterised. For each ligand structure, both diastereomers have been synthesised. These ligands are available through a straightforward procedure in good yields. The solid state structures of two diastereomeric ligands are reported. These ligands have been applied to Rh-catalysed asymmetric hydrogenations and hydroformylations of C=C bonds as well as in Ir-catalysed asymmetric hydrogenations of C=N bonds. Turnover frequencies in the range of 10,000 h(-1) and enantioselectivities of up to 98% ee have been achieved. The different chirality elements within the ligands led to marked cooperative effect in catalysis. Interestingly, there is no general privileged diastereomeric structure but rather a matched diastereomer for each application. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.011
• 作为试剂：
  描述：

  乙酸乙烯酯 、 一氧化碳 在 acetylacetonatodicarbonylrhodium(l) 、 2,2'-bis((2R,5R)-2,5-dimethylphospholan-1-yloxy)-1,1'-binaphthyl 、 氢气 、 碘 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、2.0 MPa 条件下， 反应 18.0h， 生成 (R)-2-acetoxypropanal 、 (S)-2-acetoxypropanal
  参考文献：
  名称：

  Synthesis of Binol-based diphosphinites bearing chiral phospholane units and their application in asymmetric catalysis

  摘要：

  New diphosphinite ligands based on atropoisomeric diol backbones and (R,R)-2,5-dimethylphospholane moieties have been prepared and fully characterised. For each ligand structure, both diastereomers have been synthesised. These ligands are available through a straightforward procedure in good yields. The solid state structures of two diastereomeric ligands are reported. These ligands have been applied to Rh-catalysed asymmetric hydrogenations and hydroformylations of C=C bonds as well as in Ir-catalysed asymmetric hydrogenations of C=N bonds. Turnover frequencies in the range of 10,000 h(-1) and enantioselectivities of up to 98% ee have been achieved. The different chirality elements within the ligands led to marked cooperative effect in catalysis. Interestingly, there is no general privileged diastereomeric structure but rather a matched diastereomer for each application. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.011