2-(4-Nitro-phenyl)-3-phenylamino-chromen-4-one | 208931-92-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-Nitro-phenyl)-3-phenylamino-chromen-4-one
• CAS: 208931-92-4
• 化学式: C₂₁H₁₄N₂O₄
• 分子量: 358.353
• InChiKey: AKGPBCGAFGLCPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.38
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(4-Nitro-phenyl)-3-phenylamino-chromen-4-one 在 碘苯二乙酸 作用下， 反应 6.0h， 以59%的产率得到(2R,3R)-2,3-Dimethoxy-2-(4-nitro-phenyl)-3-phenylamino-chroman-4-one
  参考文献：
  名称：

  Synthesis of <i>trans</i>-2,3-dimetho×y-3- (phenylamino)flavanones and related compounds

  摘要：

  trans-2,3-Dimethoxy-3-(phenylamino)flavanones (2), a new type of flavanone derivatives, are synthesized from flavanones or 2'-hydroxychalcones in two steps, the first one being a condensation with nitrosobenzenes (Ehrlich-Sachs reaction) and the second an oxidation with (diacetoxyiodo)benzene in methanol. Nitrone formation, an important side reaction of the Ehrlich-Sachs reaction, has also been exploited to synthesize 2 simply by use of an excess of nitrosobenzene in aqueous methanol. Syntheses of several analogues of 2 are also reported.

  DOI：

  10.1139/cjc-76-2-199
• 作为产物：
  描述：

  (E)-2'-hydroxy-4-nitrochalcone 、 亚硝基苯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以39%的产率得到2-(4-Nitro-phenyl)-3-phenylamino-chromen-4-one
  参考文献：
  名称：

  Synthesis of <i>trans</i>-2,3-dimetho×y-3- (phenylamino)flavanones and related compounds

  摘要：

  trans-2,3-Dimethoxy-3-(phenylamino)flavanones (2), a new type of flavanone derivatives, are synthesized from flavanones or 2'-hydroxychalcones in two steps, the first one being a condensation with nitrosobenzenes (Ehrlich-Sachs reaction) and the second an oxidation with (diacetoxyiodo)benzene in methanol. Nitrone formation, an important side reaction of the Ehrlich-Sachs reaction, has also been exploited to synthesize 2 simply by use of an excess of nitrosobenzene in aqueous methanol. Syntheses of several analogues of 2 are also reported.

  DOI：

  10.1139/cjc-76-2-199