2-(p-methoxyphenyl)-4-(2-benzyloxy-naphthalen-1-yl)-quinazoline | 1242459-62-6

• 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: 2-(p-methoxyphenyl)-4-(2-benzyloxy-naphthalen-1-yl)-quinazoline
• 英文别名: 2-(4-Methoxyphenyl)-4-(2-phenylmethoxynaphthalen-1-yl)quinazoline；2-(4-methoxyphenyl)-4-(2-phenylmethoxynaphthalen-1-yl)quinazoline
• CAS: 1242459-62-6
• 化学式: C₃₂H₂₄N₂O₂
• 分子量: 468.555
• InChiKey: RWASMBPNTBWTLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(p-methoxyphenyl)-4-(2-benzyloxy-naphthalen-1-yl)-quinazoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以96%的产率得到1-(2-(p-methoxyphenyl)-quinazolin-4-yl)-naphthalen-2-ol
  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：

  4-氯-2-(4-甲氧基苯基)-喹唑啉 、 (2-(苄氧基)萘-1-基)硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 以62%的产率得到2-(p-methoxyphenyl)-4-(2-benzyloxy-naphthalen-1-yl)-quinazoline
  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.