3-ethynyl-2-(phenylmethoxy)pyridine | 145143-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethynyl-2-(phenylmethoxy)pyridine
• 英文别名: 2-(Benzyloxy)-3-ethynylpyridine；3-ethynyl-2-phenylmethoxypyridine
• CAS: 145143-40-4
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: IWQYEDDKNRDHDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethynyl-2-(phenylmethoxy)pyridine 在 吡啶 、 copper diacetate 作用下， 反应 6.0h， 以76%的产率得到3,3'-(1,3-butadiyne-1,4-diyl)bis<2-(phenylmethoxy)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：

  2-苄氧基-3-溴吡啶 在 甲醇 、 氢氧化钾 、 copper(l) iodide 、 PdCl₂(PPh₃) 、 三乙胺 作用下， 反应 14.0h， 生成 3-ethynyl-2-(phenylmethoxy)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 Dipyridones and Pyridone-Pyrimidones Designed To Form Cyclic Triplexes
  作者：Eric Boucher、Michel Simard、James D. Wuest

  DOI：10.1021/jo00110a050

  日期：1995.3

  The tendency of 2-pyridones and related heterocycles to form cyclic hydrogen-bonded dimers allows them to be used as sticky sites that induce molecules in which they are incorporated to associate in particular ways. Compound 7, which is constructed from pyridone and pyrimidone subunits linked to a rigid linear acetylenic spacer, incorporates an array of hydrogen-bonding sites designed to favor the formation of a cyclic tripler. Pyridone-pyrimidone 7 was synthesized and the structure of its DMSO solvate was determined by X-ray crystallography. Aggregation does not produce a cyclic tripler but rather gives chains in which adjacent molecules of compound 7 are linked by single hydrogen bonds.