1,3-Bis[[4-(4-fluorophenyl)-2-oxochromen-7-yl]methyl]thiourea | 1229617-80-4

• 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: 1,3-Bis[[4-(4-fluorophenyl)-2-oxochromen-7-yl]methyl]thiourea
• CAS: 1229617-80-4
• 化学式: C₃₃H₂₂F₂N₂O₄S
• 分子量: 580.611
• InChiKey: MEYDDKQSBTYPSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  硫光气 、 4-(4-fluorophenyl)-7-(aminomethyl)-2H-chromen-2-one hydrochloride 在 三乙胺 作用下， 以 乙腈 为溶剂， 以70%的产率得到1,3-Bis[[4-(4-fluorophenyl)-2-oxochromen-7-yl]methyl]thiourea
  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).