2,4-diamino-6-[2-(pyrazol-1-yl)phenyl]-1,3,5-triazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-diamino-6-[2-(pyrazol-1-yl)phenyl]-1,3,5-triazine
• 英文别名: 6-(2-pyrazol-1-ylphenyl)-[1,3,5]-triazine-2,4-diamine；6-(2-Pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine；6-(2-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4-diamine
• 化学式: C₁₂H₁₁N₇
• 分子量: 253.266
• InChiKey: KLAMVORRWVBMQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异氰酸苯酯 、 2,4-diamino-6-[2-(pyrazol-1-yl)phenyl]-1,3,5-triazine 以 neat (no solvent) 为溶剂， 反应 0.75h， 以65%的产率得到1-[4-amino-6-(2-1H-pyrazol-1-ylphenyl)-[1,3,5]-triazin-2-yl]-3-phenylurea
  参考文献：
  名称：

  Microwave-assisted selective and efficient synthesis of 1,3,5-triazinyl mono and bisureas

  摘要：

  An efficient and sustainable microwave-assisted approach for the one-step preparation of a wide range of 1,3,5-triazinyl mono- and bisureas has been developed, combining solvent-free conditions and microwave irradiation. In these conditions the very unreactive amino groups of 1,3,5-triazine-2,4-diamines successfully react with phenylisocyanate to yield selectively mono and bisureas.This protocol resulted in the shortest reaction times reported so far and is generally applicable for the preparation of these valuable heterocyclic systems. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.043
• 作为产物：
  描述：

  2-(1H-吡唑-1-基)苯甲腈 、 二聚氰胺 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以52%的产率得到2,4-diamino-6-[2-(pyrazol-1-yl)phenyl]-1,3,5-triazine
  参考文献：
  名称：

  Green synthesis and self-association of 2,4-diamino-1,3,5-triazine derivatives

  摘要：

  2,4-二氨基-1,3,5-三嗪是通过在微波照射下将二氰胺与腈类反应制备的，这种方法可以被视为一种绿色程序，因为在合成和纯化过程中减少了溶剂的使用，反应时间短且过程简单。通过NMR光谱在溶液中确认了其结构。可变温度实验用于计算关于氨基-三嗪键旋转的活化自由能。三种2,4-二氨基-6-R-1,3,5-三嗪衍生物（3a: R=苯基, 3i: R=1-哌啶基和3g: R=1-苯基吡唑-3-基）的晶体结构已通过X射线分析确定。N–H⋯N相互作用因结构的不同而变化，导致从伪蜂窝网络到波纹玫瑰层的变化。

  DOI：

  10.1039/b315956f

文献信息

• Green synthesis and self-association of 2,4-diamino-1,3,5-triazine derivatives
  作者：Ángel Díaz-Ortiz、José Elguero、Concepción Foces-Foces、Antonio de la Hoz、Andrés Moreno、María del Carmen Mateo、Ana Sánchez-Migallón、Gema Valiente

  DOI：10.1039/b315956f

  日期：——

  2,4-Diamino-1,3,5-triazines have been prepared by reaction of dicyandiamide with nitriles under microwave irradiation, a method that can be considered as a green procedure due to the reduction in the use of solvents during synthesis and purification, the short reaction time and the simplicity of the procedure. The structures have been confirmed in solution by NMR spectroscopy. Variable temperature experiments have been used to calculate the free energy of activation for rotation about the amino–triazine bond. The crystal structures of three 2,4-diamino-6-R-1,3,5-triazine derivatives (3a: R = phenyl, 3i: R = 1-piperidino and 3g: R = 1-phenylpyrazol-3-yl) have been determined by X-ray analysis. The N–H⋯N interactions change from structure to structure, resulting in a variation from pseudo-honeycomb networks to corrugated rosette layers.

  2,4-二氨基-1,3,5-三嗪是通过在微波照射下将二氰胺与腈类反应制备的，这种方法可以被视为一种绿色程序，因为在合成和纯化过程中减少了溶剂的使用，反应时间短且过程简单。通过NMR光谱在溶液中确认了其结构。可变温度实验用于计算关于氨基-三嗪键旋转的活化自由能。三种2,4-二氨基-6-R-1,3,5-三嗪衍生物（3a: R=苯基, 3i: R=1-哌啶基和3g: R=1-苯基吡唑-3-基）的晶体结构已通过X射线分析确定。N–H⋯N相互作用因结构的不同而变化，导致从伪蜂窝网络到波纹玫瑰层的变化。
• Microwave-assisted selective and efficient synthesis of 1,3,5-triazinyl mono and bisureas
  作者：Amparo Ruiz-Carretero、José Ramón Ramírez、Ana Sánchez-Migallón、Antonio de la Hoz

  DOI：10.1016/j.tet.2014.01.043

  日期：2014.3

  An efficient and sustainable microwave-assisted approach for the one-step preparation of a wide range of 1,3,5-triazinyl mono- and bisureas has been developed, combining solvent-free conditions and microwave irradiation. In these conditions the very unreactive amino groups of 1,3,5-triazine-2,4-diamines successfully react with phenylisocyanate to yield selectively mono and bisureas.This protocol resulted in the shortest reaction times reported so far and is generally applicable for the preparation of these valuable heterocyclic systems. (C) 2014 Elsevier Ltd. All rights reserved.