3,3'-(1,3-butadiyne-1,4-diyl)bis-2(1H)-pyridinone | 145143-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,3'-(1,3-butadiyne-1,4-diyl)bis-2(1H)-pyridinone
• 英文别名: 3-[4-(2-oxo-1H-pyridin-3-yl)buta-1,3-diynyl]-1H-pyridin-2-one
• CAS: 145143-34-6
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: NDISQRHNMAFDFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-(1,3-butadiyne-1,4-diyl)bis-2(1H)-pyridinone 在 三氟乙酸 作用下， 反应 3.0h， 以87%的产率得到2,2'-bifuro<2,3-b>pyridine
  参考文献：
  名称：

  Use of hydrogen bonds to control molecular aggregation. Behavior of a self-complementary dipyridone designed to self-replicate

  摘要：

  In principle, the simple dipyridone 4 encodes enough chemical information to allow it to self-replicate by acting as a template for the assembly and controlled oxidative coupling of ethynylpyridone subunits 5 and 6. This could occur by the formation of ternary hydrogen-bonded complex 18, followed by copper-induced oxidative coupling of the bound ethynylpyridone subunits. In fact, treatment of an equimolar mixture of compounds 5 and 6 with excess CuCl.TMEDA and O2 in a variety of solvents produced only a normal statistical ratio of dipyridone 4 and symmetric isomers 10 and 11. This is presumably because dipyridone 4 is too highly self-associated to permit the formation of significant amounts of ternary complex 18. Moreover, even if dipyridone 4 can act as a template for the juxtaposition of its subunits, it may not be able to promote the subsequent copper-induced oxidative coupling that joins them together.

  DOI：

  10.1021/jo00053a020
• 作为产物：
  描述：

  3-ethynyl-2-(phenylmethoxy)pyridine 在 吡啶 、 copper diacetate 、 三氟乙酸 作用下， 反应 9.0h， 生成 3,3'-(1,3-butadiyne-1,4-diyl)bis-2(1H)-pyridinone
  参考文献：
  名称：

  Use of hydrogen bonds to control molecular aggregation. Behavior of a self-complementary dipyridone designed to self-replicate

  摘要：

  In principle, the simple dipyridone 4 encodes enough chemical information to allow it to self-replicate by acting as a template for the assembly and controlled oxidative coupling of ethynylpyridone subunits 5 and 6. This could occur by the formation of ternary hydrogen-bonded complex 18, followed by copper-induced oxidative coupling of the bound ethynylpyridone subunits. In fact, treatment of an equimolar mixture of compounds 5 and 6 with excess CuCl.TMEDA and O2 in a variety of solvents produced only a normal statistical ratio of dipyridone 4 and symmetric isomers 10 and 11. This is presumably because dipyridone 4 is too highly self-associated to permit the formation of significant amounts of ternary complex 18. Moreover, even if dipyridone 4 can act as a template for the juxtaposition of its subunits, it may not be able to promote the subsequent copper-induced oxidative coupling that joins them together.

  DOI：

  10.1021/jo00053a020