[3-(2-benzyloxynaphthalen-1-yl)pyridin-4-yl]dimethylamine | 719304-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [3-(2-benzyloxynaphthalen-1-yl)pyridin-4-yl]dimethylamine
• 英文别名: N,N-dimethyl-3-(2-phenylmethoxynaphthalen-1-yl)pyridin-4-amine
• CAS: 719304-50-4
• 化学式: C₂₄H₂₂N₂O
• 分子量: 354.451
• InChiKey: CUVVVGSDJJJLLU-UHFFFAOYSA-N

物化性质

• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(2-benzyloxynaphthalen-1-yl)pyridin-4-yl]dimethylamine 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 trifluoromethanesulfonic acid 1-(4-dimethylaminopyridin-3-yl)naphthalen-2-yl ester
  参考文献：
  名称：

  4-氨基吡啶的新的阻转异构联芳基衍生物—仲醇不对称酰化的改进亲核催化剂的鉴定

  摘要：

  描述了一系列基于4-二烷基氨基吡啶的阻转异构联芳基的合成，CSP-HPLC拆分和绝对构型分配。对于1-（1-萘基）乙醇的动力学拆分，这些仅对4-二烷基氨基取代基的性质不同的对映体纯催化剂的筛选揭示了该基团对催化选择性的重要性。二正丁基氨基衍生物显示出最有利的催化特性。这种催化剂用于选择的动力学拆分的效用秒-醇，包括抗抑郁药氟西汀盐酸盐（百忧解的合成的前体®被报告）。讨论了二烷基氨基在手性转移中的可能作用。

  DOI：

  10.1016/j.tet.2004.01.098
• 作为产物：
  描述：

  1-溴-2-萘酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [3-(2-benzyloxynaphthalen-1-yl)pyridin-4-yl]dimethylamine
  参考文献：
  名称：

  Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine:  A Novel Class of Chiral Nucleophilic Catalysts

  摘要：

  A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an Ar-Ar bond, has been developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core 16 by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls 31, 38, and 43 containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, respectively, have demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing Ar-Ar rotation. Biaryls containing all three cores have been shown to retain DMAP-like catalytic activity in the acylation of a hindered alcohol. Biaryls 55 and 56, which are configurationally stable at ambient temperature, have also been prepared via modification of configurationally labile derivatives. Compounds 55 and 56 in optically pure form should provide a useful starting point for studies on catalytic asymmetric acyl transfer using atropisomeric analogues of DMAP.

  DOI：

  10.1021/jo991011h

文献信息

• US7291739B2
  申请人：——

  公开号：US7291739B2

  公开（公告）日：2007-11-06
• Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine:  A Novel Class of Chiral Nucleophilic Catalysts
  作者：Alan C. Spivey、Tomasz Fekner、Sharon E. Spey、Harry Adams

  DOI：10.1021/jo991011h

  日期：1999.12.1

  A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an Ar-Ar bond, has been developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core 16 by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls 31, 38, and 43 containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, respectively, have demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing Ar-Ar rotation. Biaryls containing all three cores have been shown to retain DMAP-like catalytic activity in the acylation of a hindered alcohol. Biaryls 55 and 56, which are configurationally stable at ambient temperature, have also been prepared via modification of configurationally labile derivatives. Compounds 55 and 56 in optically pure form should provide a useful starting point for studies on catalytic asymmetric acyl transfer using atropisomeric analogues of DMAP.
• New atropisomeric biaryl derivatives of 4-aminopyridine—identification of an improved nucleophilic catalyst for asymmetric acylation of sec-alcohols
  作者：Alan C Spivey、David P Leese、Fujiang Zhu、Stephen G Davey、Richard L Jarvest

  DOI：10.1016/j.tet.2004.01.098

  日期：2004.5

  described. Screening of these enantiomerically pure catalysts, which differ only in the nature of the 4-dialkylamino substituent, for the kinetic resolution of 1-(1-naphthyl)ethanol reveals the importance of this group on the selectivity of catalysis. The di-n-butylamino derivative displays the most favourable catalytic profile. The utility of this catalyst for the kinetic resolution of a selection of sec-alcohols

  描述了一系列基于4-二烷基氨基吡啶的阻转异构联芳基的合成，CSP-HPLC拆分和绝对构型分配。对于1-（1-萘基）乙醇的动力学拆分，这些仅对4-二烷基氨基取代基的性质不同的对映体纯催化剂的筛选揭示了该基团对催化选择性的重要性。二正丁基氨基衍生物显示出最有利的催化特性。这种催化剂用于选择的动力学拆分的效用秒-醇，包括抗抑郁药氟西汀盐酸盐（百忧解的合成的前体®被报告）。讨论了二烷基氨基在手性转移中的可能作用。