3-(3-methoxy-9-xanthenylidene)-2,4-pentanedione | 141221-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(3-methoxy-9-xanthenylidene)-2,4-pentanedione
• 英文别名: 3-(3-Methoxyxanthen-9-ylidene)pentane-2,4-dione
• CAS: 141221-83-2
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: GHBIXVZMEFGLIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methoxyxanthene 、 乙酰丙酮 在 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 0.02h， 以44%的产率得到3-(3-methoxy-9-xanthenyl)-2,4-pentanedione
  参考文献：
  名称：

  Manganese(III)-mediated carbon-carbon bond formation in the reaction of xanthenes with active methylene compounds

  摘要：

  Oxidation of xanthenes with manganese(III) acetate in the presence of active methylene compounds such as 1,3-dicarbonyl compounds, malononitrile derivatives, acetone, and nitromethane selectively gives 9-substituted xanthene derivatives in good yields. A similar oxidation of thioxanthene also yields 2-(9-thioxanthenyl)-1,3-dicarbonyl compounds in 57-91% yields. The obtained 2-(9-xanthenyl)-1,3-dicarbonyl compounds are readily converted to 2-(9-xanthenylidene)-1,3-dicarbonyl derivatives using manganese(III) complexes or 2,3-dichloro-5, 6-dicyano-1,4-benzoquinone. The mechanisms for the formation of 9-substituted xanthenes are discussed on the basis of the reaction of intermediates, the electron-donating substituent effect on the xanthene ring system, effect of additives, and comparison with a reaction of radical-trapping reagents.

  DOI：

  10.1021/jo00039a010