2-(phenylmethoxy)-3-<4-<6-(phenylmethoxy)-2-pyridinyl>-1,3-butadiynyl>pyridine | 145143-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(phenylmethoxy)-3-<4-<6-(phenylmethoxy)-2-pyridinyl>-1,3-butadiynyl>pyridine
• 英文别名: 2-Phenylmethoxy-3-[4-(6-phenylmethoxypyridin-2-yl)buta-1,3-diynyl]pyridine
• CAS: 145143-38-0
• 化学式: C₂₈H₂₀N₂O₂
• 分子量: 416.479
• InChiKey: AERSHBLEWSWIEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(phenylmethoxy)-3-<4-<6-(phenylmethoxy)-2-pyridinyl>-1,3-butadiynyl>pyridine 在 三氟乙酸 作用下， 反应 1.0h， 以81%的产率得到3-<4-(1,6-dihydro-6-oxo-2-pyridinyl)-1,3-butadiynyl>-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
• 作为产物：
  描述：

  2-ethynyl-6-(phenylmethoxy)pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 溴 、 三乙胺 作用下， 以 水 为溶剂， 反应 60.0h， 生成 2-(phenylmethoxy)-3-<4-<6-(phenylmethoxy)-2-pyridinyl>-1,3-butadiynyl>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

文献信息

• Use of hydrogen bonds to control molecular aggregation. Behavior of a self-complementary dipyridone designed to self-replicate
  作者：Francois Persico、James D. Wuest

  DOI：10.1021/jo00053a020

  日期：1993.1

  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.