N²-(2,4-dimethoxybenzyl)-N⁴-ethyl-N⁶-isopropyl-1,3,5-triazine-2,4,6-triamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: N²-(2,4-dimethoxybenzyl)-N⁴-ethyl-N⁶-isopropyl-1,3,5-triazine-2,4,6-triamine
• 英文别名: 4-N-[(2,4-dimethoxyphenyl)methyl]-6-N-ethyl-2-N-propan-2-yl-1,3,5-triazine-2,4,6-triamine
• 化学式: C₁₇H₂₆N₆O₂
• 分子量: 346.432
• InChiKey: FBOISFVLPNWHJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.2
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-(2,4-dimethoxybenzyl)-N⁴-ethyl-N⁶-isopropyl-1,3,5-triazine-2,4,6-triamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以88%的产率得到N²-ethyl-N⁴-isopropyl-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Strategies for protecting and manipulating triazine derivatives

  摘要：

  Aminotriazine derivatives are available in two steps by treating chlorotriazines with acid-labile benzylic amines including triphenylmethylamine, diphenylmethylamine, and 2,4-dimethoxybenzyl-amine (Dmb-amine), followed by deprotection using trifluoroacetic acid. This high yielding (85-99%) protocol is a milder alternative to the traditional method that uses ammonia and high temperature as a route to aminotriazine derivatives. The nucleophilic substitution reaction that installs the benzylic amine on monochlorotriazine herbicide derivatives may be performed using conventional heating. Alternatively, a microwave reactor can be used to decrease the reaction times 100-fold. The intermediates in these syntheses are soluble in a range of organic solvents and amenable to chromatography. In some cases when dimethoxybenzyl groups are used, oligornerization of the dimethoxybenzyl side product upon treatment with trifluoroacetic acid yields a precipitate that facilitates purification by simple filtration. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.150
• 作为产物：
  描述：

  2,4-二甲氧基苯甲胺 、 阿特拉津 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以99%的产率得到N²-(2,4-dimethoxybenzyl)-N⁴-ethyl-N⁶-isopropyl-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Strategies for protecting and manipulating triazine derivatives

  摘要：

  Aminotriazine derivatives are available in two steps by treating chlorotriazines with acid-labile benzylic amines including triphenylmethylamine, diphenylmethylamine, and 2,4-dimethoxybenzyl-amine (Dmb-amine), followed by deprotection using trifluoroacetic acid. This high yielding (85-99%) protocol is a milder alternative to the traditional method that uses ammonia and high temperature as a route to aminotriazine derivatives. The nucleophilic substitution reaction that installs the benzylic amine on monochlorotriazine herbicide derivatives may be performed using conventional heating. Alternatively, a microwave reactor can be used to decrease the reaction times 100-fold. The intermediates in these syntheses are soluble in a range of organic solvents and amenable to chromatography. In some cases when dimethoxybenzyl groups are used, oligornerization of the dimethoxybenzyl side product upon treatment with trifluoroacetic acid yields a precipitate that facilitates purification by simple filtration. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.150

文献信息

• Strategies for protecting and manipulating triazine derivatives
  作者：Emily Hollink、Eric E. Simanek、David E. Bergbreiter

  DOI：10.1016/j.tetlet.2005.01.150

  日期：2005.3

  Aminotriazine derivatives are available in two steps by treating chlorotriazines with acid-labile benzylic amines including triphenylmethylamine, diphenylmethylamine, and 2,4-dimethoxybenzyl-amine (Dmb-amine), followed by deprotection using trifluoroacetic acid. This high yielding (85-99%) protocol is a milder alternative to the traditional method that uses ammonia and high temperature as a route to aminotriazine derivatives. The nucleophilic substitution reaction that installs the benzylic amine on monochlorotriazine herbicide derivatives may be performed using conventional heating. Alternatively, a microwave reactor can be used to decrease the reaction times 100-fold. The intermediates in these syntheses are soluble in a range of organic solvents and amenable to chromatography. In some cases when dimethoxybenzyl groups are used, oligornerization of the dimethoxybenzyl side product upon treatment with trifluoroacetic acid yields a precipitate that facilitates purification by simple filtration. (C) 2005 Elsevier Ltd. All rights reserved.