2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide | 213769-94-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide
• 英文别名: 2-Oxochromene-4-carbonitrile oxide
• CAS: 213769-94-9
• 化学式: C₁₀H₅NO₃
• 分子量: 187.155
• InChiKey: QPGRNRUHFNVHEY-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide 以 乙醚 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 4-(5-methyl-4-phenyl-5H-1,2,4-oxadiazol-3-yl)chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives

  摘要：

  A series of novel coumarin-4-carboxamidoximes 6a-g and 3-(coumarin-4-yl)-1,2,4-oxadiazoles 9a-e were synthesized from coumarin-4-carboxaldehyde 1 via the intermediate coumarin-4-nitriloxide 4. These coumarin derivatives were isolated and characterized, and evaluated for their ability to inhibit trypsin, glucuronidase, and soybean lipoxygenase. The compounds were also tested for antioxidant activity, and as antiiflammatory agents in the rat carrageenin paw edema assay. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80030-5
• 作为产物：
  描述：

  4-Oximino-2-oxo-2H-1-benzopyran 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide
  参考文献：
  名称：

  2-氧代-2 H- [1]苯并吡喃-4-腈N-氧化物的1，3-环加成反应。几种新的4-取代的香豆素的合成

  摘要：

  新的2-oxo-2 H- [1]苯并吡喃-4-腈N-氧化物2与双极性亲和剂，邻氨基苯酚和邻苯二胺的1，3-环加成反应生成4-杂环取代的香豆素衍生物。通过它们的抗蛋白水解活性，与1,1-二苯基-2-吡啶并肼基的相互作用以及影响超氧阴离子和抑制β-葡萄糖醛酸苷酶和大豆脂氧合酶的能力，筛选了这些衍生物的体外抗炎活性。

  DOI：

  10.1002/jhet.5570350321

文献信息

• 1,3-cycloaddition reactions of 2-oxo-2<i>H</i>-[1]benzopyran-4-carbonitrile<i>N</i>-oxide. Synthesis of several new 4-substituted coumarins
  作者：Demetrios N. Nicolaides、Konstantina C. Fylaktakidou、Konstantinos E. Litinas、George K. Papageorgiou、Dimitra J. Hadjipavlou-Litina

  DOI：10.1002/jhet.5570350321

  日期：1998.5

  1,3-Cycloaddition reactions of new 2-oxo-2H-[1]benzopyran-4-carbonitrile N-oxide 2 with dipolarophiles, o-aminophenols and o-phenylenediamine resulted in 4-heterocyclic substituted coumarin derivatives. These derivatives are screened for antiinflammatory activity in vitro through their antiproteolytic activity, the interaction with 1,1-diphenyl-2-picrylhydrazyl and the ability to affect superoxide

  新的2-oxo-2 H- [1]苯并吡喃-4-腈N-氧化物2与双极性亲和剂，邻氨基苯酚和邻苯二胺的1，3-环加成反应生成4-杂环取代的香豆素衍生物。通过它们的抗蛋白水解活性，与1,1-二苯基-2-吡啶并肼基的相互作用以及影响超氧阴离子和抑制β-葡萄糖醛酸苷酶和大豆脂氧合酶的能力，筛选了这些衍生物的体外抗炎活性。
• Synthesis and biological evaluation of several coumarin-4-carboxamidoxime and 3-(coumarin-4-yl)-1,2,4-oxadiazole derivatives
  作者：Demetrios N. Nicolaides、Konstantina C. Fylaktakidou、Konstantinos E. Litinas、Dimitra Hadjipavlou-Litina

  DOI：10.1016/s0223-5234(98)80030-5

  日期：1998.9

  A series of novel coumarin-4-carboxamidoximes 6a-g and 3-(coumarin-4-yl)-1,2,4-oxadiazoles 9a-e were synthesized from coumarin-4-carboxaldehyde 1 via the intermediate coumarin-4-nitriloxide 4. These coumarin derivatives were isolated and characterized, and evaluated for their ability to inhibit trypsin, glucuronidase, and soybean lipoxygenase. The compounds were also tested for antioxidant activity, and as antiiflammatory agents in the rat carrageenin paw edema assay. (C) Elsevier, Paris.