3-[2-(2-hydroxyethoxy)ethoxy]-1-methylpyridazin-6-one | 874113-83-4

• 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: 3-[2-(2-hydroxyethoxy)ethoxy]-1-methylpyridazin-6-one
• 英文别名: 6-[2-(2-hydroxyethoxy)ethoxy]-2-methylpyridazin-3-one
• CAS: 874113-83-4
• 化学式: C₉H₁₄N₂O₄
• 分子量: 214.221
• InChiKey: IJHWVXSMFQNXAX-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  352.4±48.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.58
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-[2-(2-hydroxyethoxy)ethoxy]-1-methylpyridazin-6-one 、 间二溴苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以32%的产率得到1,3-bis{2-[2-(1-methyl-6-oxopyridazin-3-yloxy)ethoxy]ethoxymethyl}benzene
  参考文献：
  名称：

  New acyclic receptors containing pyridazine units. The influence of π-stacking on the selective transport of lipophilic phenethylamines

  摘要：

  The synthesis of four new series of acyclic heteroaromatic receptors is described. They are built by two flexible polyether chains functionalised at their end with pyridazinone or methylpyridazine rings and connected by pyridine or benzene units. Their ability as carriers of lipophilic and hydrophilic phenethylamines and metallic cations has been evaluated. Transport rates show that, in general, these compounds are much more efficient carriers of lipophilic amines than of dopamine and Na+, K+ and Ca2+ ions. Their transport selectivities towards phenethylamine and homoveratrylamine are discussed on the basis of their structural features. Molecular modelling studies suggest that interaction of the aromatic moiety of the guest with the pyridazinone rings via double pi-stacking, or with the pyridine ring by single pi-stacking, should be responsible of their enhanced efficacy and selectivity in the transport of lipophilic phenethylamines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.069
• 作为产物：
  描述：

  6-氯-2-甲基吡嗪-3(2H)-酮 、 二乙二醇 在 sodium 作用下， 反应 1.0h， 以52%的产率得到3-[2-(2-hydroxyethoxy)ethoxy]-1-methylpyridazin-6-one
  参考文献：
  名称：

  New acyclic receptors containing pyridazine units. The influence of π-stacking on the selective transport of lipophilic phenethylamines

  摘要：

  The synthesis of four new series of acyclic heteroaromatic receptors is described. They are built by two flexible polyether chains functionalised at their end with pyridazinone or methylpyridazine rings and connected by pyridine or benzene units. Their ability as carriers of lipophilic and hydrophilic phenethylamines and metallic cations has been evaluated. Transport rates show that, in general, these compounds are much more efficient carriers of lipophilic amines than of dopamine and Na+, K+ and Ca2+ ions. Their transport selectivities towards phenethylamine and homoveratrylamine are discussed on the basis of their structural features. Molecular modelling studies suggest that interaction of the aromatic moiety of the guest with the pyridazinone rings via double pi-stacking, or with the pyridine ring by single pi-stacking, should be responsible of their enhanced efficacy and selectivity in the transport of lipophilic phenethylamines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.069

文献信息

• New acyclic receptors containing pyridazine units. The influence of π-stacking on the selective transport of lipophilic phenethylamines
  作者：Lucrecia Campayo、Fabián Calzado、M. Carmen Cano、María J.R. Yunta、Mercedes Pardo、Pilar Navarro、M. Luisa Jimeno、Fernando Gómez-Contreras、Ana M. Sanz

  DOI：10.1016/j.tet.2005.09.069

  日期：2005.12

  The synthesis of four new series of acyclic heteroaromatic receptors is described. They are built by two flexible polyether chains functionalised at their end with pyridazinone or methylpyridazine rings and connected by pyridine or benzene units. Their ability as carriers of lipophilic and hydrophilic phenethylamines and metallic cations has been evaluated. Transport rates show that, in general, these compounds are much more efficient carriers of lipophilic amines than of dopamine and Na+, K+ and Ca2+ ions. Their transport selectivities towards phenethylamine and homoveratrylamine are discussed on the basis of their structural features. Molecular modelling studies suggest that interaction of the aromatic moiety of the guest with the pyridazinone rings via double pi-stacking, or with the pyridine ring by single pi-stacking, should be responsible of their enhanced efficacy and selectivity in the transport of lipophilic phenethylamines. (c) 2005 Elsevier Ltd. All rights reserved.