4,4'-dimethoxy-2,5'-bipyrimidine | 219915-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4,4'-dimethoxy-2,5'-bipyrimidine
• 英文别名: 4-Methoxy-2-(4-methoxypyrimidin-5-yl)pyrimidine
• CAS: 219915-25-0
• 化学式: C₁₀H₁₀N₄O₂
• 分子量: 218.215
• InChiKey: QXSHAPPROVNKQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-dimethoxy-2,5'-bipyrimidine 在 氢氧化钾 作用下， 反应 1.0h， 以65%的产率得到<2,5'-bipyrimidine>-4,4-'(3H,3'H)-dione
  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：

  4-氯-6-甲氧基嘧啶 在 palladium on activated charcoal 、 magnesium oxide 氢气 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 74.08h， 生成 4,4'-dimethoxy-2,5'-bipyrimidine
  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.