5-{[2-(2-propynyloxy)-1-naphthyl]methylene}-2,4,6(1H,3H,5H)-pyrimidinetrione | 365519-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-{[2-(2-propynyloxy)-1-naphthyl]methylene}-2,4,6(1H,3H,5H)-pyrimidinetrione
• 英文别名: 5-[(2-Prop-2-ynoxynaphthalen-1-yl)methylidene]-1,3-diazinane-2,4,6-trione
• CAS: 365519-45-5
• 化学式: C₁₈H₁₂N₂O₄
• 分子量: 320.304
• InChiKey: FWSISXXRANKKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-{[2-(2-propynyloxy)-1-naphthyl]methylene}-2,4,6(1H,3H,5H)-pyrimidinetrione 在 copper(l) iodide 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以72%的产率得到
  参考文献：
  名称：

  Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI

  摘要：

  A new method for the preparation of tetracyclic uracils (oxa-helicene) 4 was developed. The intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadiene 3 and an unactivated alkyne in the presence of CuI led to tetracyclic uracils 4 in aqueous media with good yields. The 1-oxa-1,3-butadiene 3 was prepared through Knoevenagel reaction of O-propargylated salicylaldehyde derivatives and barbituric acid or 1,3-dimethylbarbituric acid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.08.056
• 作为产物：
  描述：

  巴比妥酸 、 2-(2-丙炔氧基)-1-萘醛 在 盐酸 作用下， 以93%的产率得到5-{[2-(2-propynyloxy)-1-naphthyl]methylene}-2,4,6(1H,3H,5H)-pyrimidinetrione
  参考文献：
  名称：

  Intramolecular hetero-Diels–Alder reaction of 1-oxa-1,3-butadienes with terminal acetylenes in aqueous media using CuI

  摘要：

  A new method for the preparation of tetracyclic uracils (oxa-helicene) 4 was developed. The intramolecular hetero-Diels-Alder reaction of 1-oxa-1,3-butadiene 3 and an unactivated alkyne in the presence of CuI led to tetracyclic uracils 4 in aqueous media with good yields. The 1-oxa-1,3-butadiene 3 was prepared through Knoevenagel reaction of O-propargylated salicylaldehyde derivatives and barbituric acid or 1,3-dimethylbarbituric acid. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.08.056