4',6-dimethoxy-3-fluoroflavone

• 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: 4',6-dimethoxy-3-fluoroflavone
• 英文别名: 3-fluoro-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one；3-Fluoro-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• 化学式: C₁₇H₁₃FO₄
• 分子量: 300.286
• InChiKey: BQLXTTHPVFOIIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-双(4-甲氧基苯基)1,3-丙二酮 在 N-氯代丁二酰亚胺 、 lithium perchlorate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 23.5h， 生成 4',6-dimethoxy-3-fluoroflavone
  参考文献：
  名称：

  Photocyclization of 2-Chloro-Substituted 1,3-Diarylpropan-1,3-diones to Flavones

  摘要：

  The photochemical behavior of 2-halo-substituted 1,3-diarylpropan-1,3-dione strongly depends on the nature of the halogen atom bonded and the presence of electron-donor groups on the phenyl ring. In the case of 2-chloro-1,3-diphenylpropan-1,3-dione and 1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione, cyclization to flavones was the sole reaction pathway, whereas in the case of 2-chloro-1,3-di(4-methoxyphenyl)propan-1,3-dione, only products derived from alpha-cleavage were observed. 2-Fluoro derivatives of 1,3-diarylpropan-1,3-diones were photostable; on the other hand, 2-chloro-2-fluoro derivates resulted in 3-fluoroflavones.

  DOI：

  10.1021/ol701654c

文献信息

• One-pot synthesis of 3-fluoroflavones <i>via</i> 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones and selectfluor at room temperature
  作者：Rui Wang、Jie Han、Chenchen Li、Jie Zhang、Yong Liang、Tao Wang、Zunting Zhang

  DOI：10.1039/c8ob00135a

  日期：——

  developed. 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones were fluorinated using selectfluor with a small amount of CH3CN at room temperature, followed by cyclization and dehydration in the presence of a trace amount of conc. H2SO4 to provide 3-fluoroflavones. The desired 3-fluoroflavone analogues were obtained in moderate to excellent yields. This strategy tolerated a wide range of functional groups and

  开发了一种简洁高效的一锅法合成3-氟黄酮。在室温下，使用带有少量CH 3 CN的selectfluor对1-（2-羟基苯基）-3-苯基丙烷-1,3-二酮进行氟化，然后在痕量浓盐酸存在下进行环化和脱水。H 2 SO 4提供3-氟黄酮。以中等至优异的产率获得了所需的3-氟黄酮类似物。该策略可耐受各种官能团，不需要复杂的仪器或繁琐的底物制备。
• Photocyclization of 2-Chloro-Substituted 1,3-Diarylpropan-1,3-diones to Flavones
  作者：Berta Košmrlj、Boris Šket

  DOI：10.1021/ol701654c

  日期：2007.9.1

  The photochemical behavior of 2-halo-substituted 1,3-diarylpropan-1,3-dione strongly depends on the nature of the halogen atom bonded and the presence of electron-donor groups on the phenyl ring. In the case of 2-chloro-1,3-diphenylpropan-1,3-dione and 1-(3,5-dimethoxyphenyl)-3-phenylpropan-1,3-dione, cyclization to flavones was the sole reaction pathway, whereas in the case of 2-chloro-1,3-di(4-methoxyphenyl)propan-1,3-dione, only products derived from alpha-cleavage were observed. 2-Fluoro derivatives of 1,3-diarylpropan-1,3-diones were photostable; on the other hand, 2-chloro-2-fluoro derivates resulted in 3-fluoroflavones.