4-(4-Fluorophenyl)-2-oxochromene-7-carboxylic acid | 1229617-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(4-Fluorophenyl)-2-oxochromene-7-carboxylic acid
• CAS: 1229617-73-5
• 化学式: C₁₆H₉FO₄
• 分子量: 284.243
• InChiKey: KSLKDZHQAYVMGA-UHFFFAOYSA-N

物化性质

• 沸点：
  489.3±45.0 °C(predicted)
• 密度：
  1.450±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  一氧化碳 、 4-(4-fluorophenyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate 在 三乙基硅烷 、 1,3-双(二苯基膦)丙烷 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、689.49 kPa 条件下， 反应 1.0h， 以49%的产率得到4-(4-fluorophenyl)-2-oxo-2H-chromene-7-carboxaldehyde
  参考文献：
  名称：

  A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633

  摘要：

  Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesullonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).

  DOI：

  10.1021/jo100561u

文献信息

• A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633
  作者：Francis Gosselin、Robert A. Britton、Ian W. Davies、Sarah J. Dolman、Danny Gauvreau、R. Scott Hoerrner、Gregory Hughes、Jacob Janey、Stephen Lau、Carmela Molinaro、Christian Nadeau、Paul D. O’Shea、Michael Palucki、Rick Sidler

  DOI：10.1021/jo100561u

  日期：2010.6.18

  Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesullonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).