2,3-dichloro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-1,4-benzoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dichloro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-1,4-benzoquinone
• 英文别名: 2-(4-Tert-butylpyridin-1-ium-1-yl)-5,6-dichloro-3,4-dioxocyclohexa-1,5-dien-1-olate
• 化学式: C₁₅H₁₃Cl₂NO₃
• 分子量: 326.179
• InChiKey: TWNKPJPLLVGDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-叔丁基吡啶 、 四氯苯醌 以 乙醚 为溶剂， 反应 18.0h， 以53.6%的产率得到2,3-dichloro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-1,4-benzoquinone
  参考文献：
  名称：

  Stability of Pyridiniumylquinones to Aqueous Media:  The Formation of Pyridinium−Oxy Zwitterionic Quinones

  摘要：

  The stability of perpyridiniumyl- and halopyridiniumylbenzoquinones was investigated. Reactions of p-chloranil and p-fluoranil with pyridines, followed by hydrolysis under mild conditions, gave 2,3-dihalo-5-oxy-6-(pyridinium-1'-yl)-1,4-benzoquinones 1 and 2,5-dioxy-3,6-bis(pyridinium-1'-yl)-1,4-benzoquinone 2. Using the H-0 technique, the aqueous pK(a)'s for two of these pyridinium-oxy zwitterions were determined to be -3 for 2,5-bis(4'-tert-butylpyridinium-1'-yl)-3,6-dioxy-1,4-benzoquinone(2) and -2 for 2,3-dichloro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-3,6-dioxy-1,4-benzoquinone (1a). In addition, it was found that a pyridinium-substituted anthraquinone, 1-[4'-(dimethylamino)-pyridinium-1'-yl]anthraquinone (3), is quite stable toward hydrolysis conditions and shows two reversible reductions at E(1/2) = -0.69 and -1.10 V vs SCE.

  DOI：

  10.1021/jo9600924

文献信息

• Stability of Pyridiniumylquinones to Aqueous Media:  The Formation of Pyridinium−Oxy Zwitterionic Quinones
  作者：Andrew S. Koch、Warren Grant Harbison、Joshua M. Hubbard、Martin de Kort、Barbara A. Roe

  DOI：10.1021/jo9600924

  日期：1996.1.1

  The stability of perpyridiniumyl- and halopyridiniumylbenzoquinones was investigated. Reactions of p-chloranil and p-fluoranil with pyridines, followed by hydrolysis under mild conditions, gave 2,3-dihalo-5-oxy-6-(pyridinium-1'-yl)-1,4-benzoquinones 1 and 2,5-dioxy-3,6-bis(pyridinium-1'-yl)-1,4-benzoquinone 2. Using the H-0 technique, the aqueous pK(a)'s for two of these pyridinium-oxy zwitterions were determined to be -3 for 2,5-bis(4'-tert-butylpyridinium-1'-yl)-3,6-dioxy-1,4-benzoquinone(2) and -2 for 2,3-dichloro-5-oxy-6-(4'-tert-butylpyridinium-1'-yl)-3,6-dioxy-1,4-benzoquinone (1a). In addition, it was found that a pyridinium-substituted anthraquinone, 1-[4'-(dimethylamino)-pyridinium-1'-yl]anthraquinone (3), is quite stable toward hydrolysis conditions and shows two reversible reductions at E(1/2) = -0.69 and -1.10 V vs SCE.