[4-(naphthalen-2-ylmethoxy)pyridine-2,6-diyl]dimethanol | 1245504-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [4-(naphthalen-2-ylmethoxy)pyridine-2,6-diyl]dimethanol
• 英文别名: [6-(Hydroxymethyl)-4-(naphthalen-2-ylmethoxy)pyridin-2-yl]methanol；[6-(hydroxymethyl)-4-(naphthalen-2-ylmethoxy)pyridin-2-yl]methanol
• CAS: 1245504-07-7
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: KDMBVPYCMLVVLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(naphthalen-2-ylmethoxy)pyridine-2,6-diyl]dimethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到4-(naphthalen-2-ylmethoxy)pyridine-2,6-dicarboxaldehyde
  参考文献：
  名称：

  Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

  摘要：

  A family of pyridine based dialdehydes has been efficiently prepared starting from chelidamic acid by chemical modification of its 4-hydroxyl group. The condensation of these dialdehydes with commercially available (1R,2R)-(-)-cyclohexane-1,2-diamine in the presence of Ba2+ template led, after the in situ reduction, to the synthesis of a family of enantiopure hexaazapyridinophanes substituted at the periphery. These new receptors have been used as chiral shift agents towards different carboxylic acids. Good splitting of the carboxylic acid NMR signals (up to Delta Delta delta=0.13 ppm) were observed using substoichiometrical amount of the receptor. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.009
• 作为产物：
  描述：

  diethyl 4-(naphthalen-2-ylmethoxy)pyridine-2,6-dicarboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以84%的产率得到[4-(naphthalen-2-ylmethoxy)pyridine-2,6-diyl]dimethanol
  参考文献：
  名称：

  Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

  摘要：

  A family of pyridine based dialdehydes has been efficiently prepared starting from chelidamic acid by chemical modification of its 4-hydroxyl group. The condensation of these dialdehydes with commercially available (1R,2R)-(-)-cyclohexane-1,2-diamine in the presence of Ba2+ template led, after the in situ reduction, to the synthesis of a family of enantiopure hexaazapyridinophanes substituted at the periphery. These new receptors have been used as chiral shift agents towards different carboxylic acids. Good splitting of the carboxylic acid NMR signals (up to Delta Delta delta=0.13 ppm) were observed using substoichiometrical amount of the receptor. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.009

文献信息

• Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids
  作者：Eduardo Busto、Almudena González-Álvarez、Vicente Gotor-Fernández、Ignacio Alfonso、Vicente Gotor

  DOI：10.1016/j.tet.2010.06.009

  日期：2010.8

  A family of pyridine based dialdehydes has been efficiently prepared starting from chelidamic acid by chemical modification of its 4-hydroxyl group. The condensation of these dialdehydes with commercially available (1R,2R)-(-)-cyclohexane-1,2-diamine in the presence of Ba2+ template led, after the in situ reduction, to the synthesis of a family of enantiopure hexaazapyridinophanes substituted at the periphery. These new receptors have been used as chiral shift agents towards different carboxylic acids. Good splitting of the carboxylic acid NMR signals (up to Delta Delta delta=0.13 ppm) were observed using substoichiometrical amount of the receptor. (c) 2010 Elsevier Ltd. All rights reserved.