2-<(4-bromophenyl)ethynyl>-4-methoxypyrimidine | 219915-21-6

• 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: 2-<(4-bromophenyl)ethynyl>-4-methoxypyrimidine
• 英文别名: 2-[2-(4-Bromophenyl)ethynyl]-4-methoxypyrimidine
• CAS: 219915-21-6
• 化学式: C₁₃H₉BrN₂O
• 分子量: 289.131
• InChiKey: QOWJUMPUJKZGQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(4-bromophenyl)ethynyl>-4-methoxypyrimidine 在 bis-triphenylphosphine-palladium(II) chloride 、 氢氧化钾 、 正丁基锂 、 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 2,5'-(1,4-phenylenedi-2,1-ethynediyl)bis<4(3H)-pyrimidinone>
  参考文献：
  名称：

  Synthesis and Self-Association of 4-Pyrimidinones

  摘要：

  Crystallization of 4-pyrimidinone from CHCl3 produced colorless needles that were shown by X-ray crystallography to consist of cyclic hydrogen-bonded dimers 2 of the 4(3H)-pyrimidinone tautomer 1. Vapor-pressure osmometry established that a simple derivative, 5-(2-phenylethyl)-4(3H)-pyrimidinone (5), self-associates in solution with a value of K-a (220 +/- 110 m(-1) at 26 degrees C in CH2Cl2) close to that measured for 2-pyridinone under similar conditions. These observations suggest that 4-pyrimidinones and 2-pyridinones have similar modes and degrees of association and should be equally suitable for use as sticky functional groups that can be incorporated in complex molecules to make them associate in particular ways. This hypothesis was tested by synthesizing three dipyrimidinones (12, 16, and 21) designed to form strongly hydrogen-bonded dimers and by making a tetrapyrimidinone (26) designed to self-associate and to thereby generate a three-dimensional hydrogen-bonded network. In all cases, however, the compounds proved to have very low solubilities in organic solvents, and crystals suitable for X-ray diffraction could not be obtained despite intensive effort. It is possible that the simultaneous presence of multiple tautomers, all capable of strong intermolecular association? disfavors the sustained growth of single crystalline phases.

  DOI：

  10.1021/jo981285p
• 作为产物：
  描述：

  对溴碘苯 、 2-乙炔基-4-甲氧基嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 24.0h， 以91%的产率得到2-<(4-bromophenyl)ethynyl>-4-methoxypyrimidine
  参考文献：
  名称：

  Synthesis and Self-Association of 4-Pyrimidinones

  摘要：

  Crystallization of 4-pyrimidinone from CHCl3 produced colorless needles that were shown by X-ray crystallography to consist of cyclic hydrogen-bonded dimers 2 of the 4(3H)-pyrimidinone tautomer 1. Vapor-pressure osmometry established that a simple derivative, 5-(2-phenylethyl)-4(3H)-pyrimidinone (5), self-associates in solution with a value of K-a (220 +/- 110 m(-1) at 26 degrees C in CH2Cl2) close to that measured for 2-pyridinone under similar conditions. These observations suggest that 4-pyrimidinones and 2-pyridinones have similar modes and degrees of association and should be equally suitable for use as sticky functional groups that can be incorporated in complex molecules to make them associate in particular ways. This hypothesis was tested by synthesizing three dipyrimidinones (12, 16, and 21) designed to form strongly hydrogen-bonded dimers and by making a tetrapyrimidinone (26) designed to self-associate and to thereby generate a three-dimensional hydrogen-bonded network. In all cases, however, the compounds proved to have very low solubilities in organic solvents, and crystals suitable for X-ray diffraction could not be obtained despite intensive effort. It is possible that the simultaneous presence of multiple tautomers, all capable of strong intermolecular association? disfavors the sustained growth of single crystalline phases.

  DOI：

  10.1021/jo981285p

文献信息

• Synthesis and Self-Association of 4-Pyrimidinones
  作者：Louis Vaillancourt、Michel Simard、James D. Wuest

  DOI：10.1021/jo981285p

  日期：1998.12.1

  Crystallization of 4-pyrimidinone from CHCl3 produced colorless needles that were shown by X-ray crystallography to consist of cyclic hydrogen-bonded dimers 2 of the 4(3H)-pyrimidinone tautomer 1. Vapor-pressure osmometry established that a simple derivative, 5-(2-phenylethyl)-4(3H)-pyrimidinone (5), self-associates in solution with a value of K-a (220 +/- 110 m(-1) at 26 degrees C in CH2Cl2) close to that measured for 2-pyridinone under similar conditions. These observations suggest that 4-pyrimidinones and 2-pyridinones have similar modes and degrees of association and should be equally suitable for use as sticky functional groups that can be incorporated in complex molecules to make them associate in particular ways. This hypothesis was tested by synthesizing three dipyrimidinones (12, 16, and 21) designed to form strongly hydrogen-bonded dimers and by making a tetrapyrimidinone (26) designed to self-associate and to thereby generate a three-dimensional hydrogen-bonded network. In all cases, however, the compounds proved to have very low solubilities in organic solvents, and crystals suitable for X-ray diffraction could not be obtained despite intensive effort. It is possible that the simultaneous presence of multiple tautomers, all capable of strong intermolecular association? disfavors the sustained growth of single crystalline phases.