4-[6-(4-Carboxyphenoxy)hexa-2,4-diynoxy]benzoic acid | 166983-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[6-(4-Carboxyphenoxy)hexa-2,4-diynoxy]benzoic acid
• 英文别名: 4-[6-(4-carboxyphenoxy)hexa-2,4-diynoxy]benzoic acid
• CAS: 166983-90-0
• 化学式: C₂₀H₁₄O₆
• 分子量: 350.328
• InChiKey: VPNNWYSMJWRZQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-羟基间苯二甲酸二甲酯 在 copper(II) choride dihydrate 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 4-[6-(4-Carboxyphenoxy)hexa-2,4-diynoxy]benzoic acid 、 4-((6-(3,5-bis(methoxycarbonyl)phenoxy)hexa-2,4-diyn-1-yl)oxy)benzoic acid
  参考文献：
  名称：

  One-pot esterification-click (CuAAC) and esterification–acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin

  摘要：

  We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.034

文献信息

• One-pot esterification-click (CuAAC) and esterification–acetylene coupling (Glaser/Eglinton) for functionalization of Wang polystyrene resin
  作者：Sagi Eppel、Moshe Portnoy

  DOI：10.1016/j.tetlet.2013.07.034

  日期：2013.9

  We report three new sets of one-pot reactions for functionalization of Wang polystyrene resin and its derivatives. We first show that it is possible to combine esterification and CuAAC (Copper-Catalyzed Alkyne-Azide Cycloaddition) in a one-pot reaction with a very high yield. We also demonstrate for the first time that it is possible to combine esterification with either Glaser or Eglinton acetylene-couplings in a one-pot reaction. Finally, we show that the esterification, CuAAC, and Glaser-coupling reactions are all compatible with each other, and it is possible to run in parallel esterification/CuAAC and esterification/Glaser coupling in a single vessel. All reactions are performed at room temperature while the only separation method required is filtering and washing the resin. (C) 2013 Elsevier Ltd. All rights reserved.