(+/-)-diethyl[3-(2-[1,1';3',1'']terphenyl-5'-yl-naphthalen-1-yl)pyridin-4-yl]amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-diethyl[3-(2-[1,1';3',1'']terphenyl-5'-yl-naphthalen-1-yl)pyridin-4-yl]amine
• 英文别名: 3-[2-(3,5-diphenylphenyl)naphthalen-1-yl]-N,N-diethylpyridin-4-amine
• 化学式: C₃₇H₃₂N₂
• 分子量: 504.674
• InChiKey: AIBZLLSQJSBHJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3,5-二苯基苯)硼酸 、 1-(4-diethylaminopyridin-3-yl)naphthalen-2-yl trifluoromethanesulfonate 在 palladium diacetate potassium phosphate 、 lithium chloride 、 2-(二环己基膦基)联苯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以50%的产率得到(+/-)-diethyl[3-(2-[1,1';3',1'']terphenyl-5'-yl-naphthalen-1-yl)pyridin-4-yl]amine
  参考文献：
  名称：

  Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis

  摘要：

  Two new atropisomeric 4-aminopyridine-based nucleophilic catalysts containing terphenyl 'blocking groups' have been prepared and evaluated for kinetic resolution (KR) of aryl alkyl sec-alcohols. One of these biaryls is shown to be the most selective atropisomeric catalyst yet prepared for several sec-alcohols but its low reactivity makes it non-optimal for use at room temperature (rt). Optimisation of the conditions for conducting KRs at rt using a previously described catalyst (containing a phenyl blocking group) at the 1 mol% level indicates that PPh3 (1 equiv) is beneficial for enantioselectivity and allows KR of (+/-)-1-(naphthyl)ethanol in less than 30 min with s > 15 (i.e. similar to 40% recovered alcohol with > 95% ee). These conditions constitute a convenient and practical method for rapid KR of sec-alcohols and are anticipated to facilitate a detailed kinetic study of this catalytic manifold by calorimetry. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.124

文献信息

• Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis
  作者：Alan C. Spivey、Stellios Arseniyadis、Tomasz Fekner、Adrian Maddaford、David P. Leese

  DOI：10.1016/j.tet.2005.08.124

  日期：2006.1

  Two new atropisomeric 4-aminopyridine-based nucleophilic catalysts containing terphenyl 'blocking groups' have been prepared and evaluated for kinetic resolution (KR) of aryl alkyl sec-alcohols. One of these biaryls is shown to be the most selective atropisomeric catalyst yet prepared for several sec-alcohols but its low reactivity makes it non-optimal for use at room temperature (rt). Optimisation of the conditions for conducting KRs at rt using a previously described catalyst (containing a phenyl blocking group) at the 1 mol% level indicates that PPh3 (1 equiv) is beneficial for enantioselectivity and allows KR of (+/-)-1-(naphthyl)ethanol in less than 30 min with s > 15 (i.e. similar to 40% recovered alcohol with > 95% ee). These conditions constitute a convenient and practical method for rapid KR of sec-alcohols and are anticipated to facilitate a detailed kinetic study of this catalytic manifold by calorimetry. (c) 2005 Elsevier Ltd. All rights reserved.