3-nitro-4-phenoxy-2H-1-benzopyran-2-one | 139722-41-1

• 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: 3-nitro-4-phenoxy-2H-1-benzopyran-2-one
• 英文别名: 3-Nitro-4-phenoxy-2H-chromen-2-one；3-nitro-4-phenoxychromen-2-one
• CAS: 139722-41-1
• 化学式: C₁₅H₉NO₅
• mdl: MFCD00416526
• 分子量: 283.24
• InChiKey: XTTIBAZZBUWMHG-UHFFFAOYSA-N

物化性质

• 沸点：
  415.9±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯-3-硝基香豆素 、 苯酚 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以80%的产率得到3-nitro-4-phenoxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Anionic spirocyclization of 3-nitro-4-(2-hydroxyphenoxy)-2H-1-benzopyran-2-one: Formation of stabilized meisenheimer-type salts

  摘要：

  The interaction of 3-nitro- and 3,6-dinitro-4-(2-hydroxy-4,5-R2-phenoxy)-2H-1-benzopyran-2-ones 4a-d with triethylamine leads to the formation of triethylammonium salts of corresponding anionic spirocyclic compounds 5a-d as a result of intramolecular nucleophilic attack of aroxide-ion on position 4 of the benzopyran system. The structures are proved by H NMR, IR spectroscopy and X-ray analysis of 5c. The distribution of electron density in the model anion M was calculated from X-ray data.

  DOI：

  10.1016/s0040-4020(01)89009-8

文献信息

• Anionic spirocyclization of 3-nitro-4-(2-hydroxyphenoxy)-2H-1-benzopyran-2-one: Formation of stabilized meisenheimer-type salts
  作者：V.N. Drozd、V.N. Knyazev、N.L. Nam、D.S. Yufit、Yu.T. Struchkov、I.V. Stankevich、A.L. Chistyakov、V.P. Lezina、T.Ya. Mozhaeva、V.L. Saveljev

  DOI：10.1016/s0040-4020(01)89009-8

  日期：——

  The interaction of 3-nitro- and 3,6-dinitro-4-(2-hydroxy-4,5-R2-phenoxy)-2H-1-benzopyran-2-ones 4a-d with triethylamine leads to the formation of triethylammonium salts of corresponding anionic spirocyclic compounds 5a-d as a result of intramolecular nucleophilic attack of aroxide-ion on position 4 of the benzopyran system. The structures are proved by H NMR, IR spectroscopy and X-ray analysis of 5c. The distribution of electron density in the model anion M was calculated from X-ray data.