1-(2-(p-trifluoromethylphenyl)-quinazolin-4-yl)-naphthalen-2-ol | 1242459-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-(p-trifluoromethylphenyl)-quinazolin-4-yl)-naphthalen-2-ol
• CAS: 1242459-63-7
• 化学式: C₂₅H₁₅F₃N₂O
• 分子量: 416.402
• InChiKey: LYZDXTXBEFSOLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  46.01
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 1-(2-(p-trifluoromethylphenyl)-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92%的产率得到1-(2-(p-trifluoromethylphenyl)-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
• 作为产物：
  描述：

  2-(p-trifluoromethylphenyl)-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92%的产率得到1-(2-(p-trifluoromethylphenyl)-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