1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-2-naphthyl(trifluoromethyl)sulfonate | 1242459-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-2-naphthyl(trifluoromethyl)sulfonate
• 英文别名: [1-[2-(4-Methoxyphenyl)quinazolin-4-yl]naphthalen-2-yl] trifluoromethanesulfonate；[1-[2-(4-methoxyphenyl)quinazolin-4-yl]naphthalen-2-yl] trifluoromethanesulfonate
• CAS: 1242459-69-3
• 化学式: C₂₆H₁₇F₃N₂O₄S
• 分子量: 510.493
• InChiKey: FFPSFFARBWMASQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-2-naphthyl(trifluoromethyl)sulfonate 、 二苯基膦 在 三乙烯二胺 、 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 以60%的产率得到(R,S)-diphenyl(1-(2-(p-methoxyphenyl)-quinazolin-4-yl)(2-naphthyl))phosphine
  参考文献：
  名称：

  Rhodium-catalysed hydroboration employing new Quinazolinap ligands; an investigation into electronic effects

  摘要：

  As part of an ongoing effort to improve the efficiency and substrate scope of our Quinazolinap ligand series in the rhodium-catalysed asymmetric hydroboration of vinyl arenes, 2-(p-trifluoromethylphenyl)Quinazolinap and 2-(p-methoxyphenyl)-Quinazolinap have been synthesised and resolved in good yield. These, along with the previously reported 2-(2-pyridyl)-Quinazolinap and 2-(2-pyrazinyl)-Quinazolinap, form part of an electronic series of Quinazolinap ligands synthesised in order to explore electronic effects in this ligand class. The application of this series of ligands to the rhodium-catalysed asymmetric hydroboration of a range of vinylarenes is described. Good conversions and regioselectivities as well as excellent enantioselectivities up to 97% were obtained. 2-(p-Methoxyphenyl)-Quinazolinap demonstrated consistently high enantioselectivities in the hydroboration of sterically demanding vinylarenes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.012
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-naphthalen-2-ol 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-2-naphthyl(trifluoromethyl)sulfonate
  参考文献：
  名称：

  Rhodium-catalysed hydroboration employing new Quinazolinap ligands; an investigation into electronic effects

  摘要：

  As part of an ongoing effort to improve the efficiency and substrate scope of our Quinazolinap ligand series in the rhodium-catalysed asymmetric hydroboration of vinyl arenes, 2-(p-trifluoromethylphenyl)Quinazolinap and 2-(p-methoxyphenyl)-Quinazolinap have been synthesised and resolved in good yield. These, along with the previously reported 2-(2-pyridyl)-Quinazolinap and 2-(2-pyrazinyl)-Quinazolinap, form part of an electronic series of Quinazolinap ligands synthesised in order to explore electronic effects in this ligand class. The application of this series of ligands to the rhodium-catalysed asymmetric hydroboration of a range of vinylarenes is described. Good conversions and regioselectivities as well as excellent enantioselectivities up to 97% were obtained. 2-(p-Methoxyphenyl)-Quinazolinap demonstrated consistently high enantioselectivities in the hydroboration of sterically demanding vinylarenes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.012

文献信息

• Rhodium-catalysed hydroboration employing new Quinazolinap ligands; an investigation into electronic effects
  作者：Aoife C. Maxwell、Susan P. Flanagan、Richard Goddard、Patrick J. Guiry

  DOI：10.1016/j.tetasy.2010.06.012

  日期：2010.6

  As part of an ongoing effort to improve the efficiency and substrate scope of our Quinazolinap ligand series in the rhodium-catalysed asymmetric hydroboration of vinyl arenes, 2-(p-trifluoromethylphenyl)Quinazolinap and 2-(p-methoxyphenyl)-Quinazolinap have been synthesised and resolved in good yield. These, along with the previously reported 2-(2-pyridyl)-Quinazolinap and 2-(2-pyrazinyl)-Quinazolinap, form part of an electronic series of Quinazolinap ligands synthesised in order to explore electronic effects in this ligand class. The application of this series of ligands to the rhodium-catalysed asymmetric hydroboration of a range of vinylarenes is described. Good conversions and regioselectivities as well as excellent enantioselectivities up to 97% were obtained. 2-(p-Methoxyphenyl)-Quinazolinap demonstrated consistently high enantioselectivities in the hydroboration of sterically demanding vinylarenes. (C) 2010 Elsevier Ltd. All rights reserved.