(R)-3-(4-trifluoromethoxybenzyl)-1-(3,5-dichlorophenyl)-6-bromo-3-methyl-1H-imidazo[1,2a]imidazole-2-one | 1246745-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-(4-trifluoromethoxybenzyl)-1-(3,5-dichlorophenyl)-6-bromo-3-methyl-1H-imidazo[1,2a]imidazole-2-one
• CAS: 1246745-50-5
• 化学式: C₂₀H₁₃BrCl₂F₃N₃O₂
• 分子量: 535.147
• InChiKey: NXOXCPVSEMILTG-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (R)-1-(3,5-dichloro-phenyl)-3-methyl-3-(4-trifluoromethoxy-benzyl)-1H-imidazo[1,2-a]-imidazol-2-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 醋酸异丙酯 为溶剂， 反应 1.0h， 生成 (R)-3-(4-trifluoromethoxybenzyl)-1-(3,5-dichlorophenyl)-5-bromo-3-methyl-1H-imidazo[1,2a]imidazole-2-one 、 (R)-3-(4-trifluoromethoxybenzyl)-1-(3,5-dichlorophenyl)-6-bromo-3-methyl-1H-imidazo[1,2a]imidazole-2-one 、 (R)-3-(4-trifluoromethoxybenzyl)-1-(3,5-dichlorophenyl)-5,6-dibromo-3-methyl-1H-imidazo[1,2a]imidazole-2-one
  参考文献：
  名称：

  Efficient Synthesis of a Small Molecule, Nonpeptide Inhibitor of LFA-1

  摘要：

  A three-stage process for the synthesis of LFA-1 inhibitor 1 from amine 4 with an overall yield of 65% is described. The key stage involves a Ph(3)PCl(2)-induced dehydration/cyclization of urea 6 followed by a regioselective bromination to give (1)H-imidazo[1,2-a]imidazol-2-one 9. Br/Mg exchange of 9 followed by addition to SO(2) in THF and subsequent oxidation produces a sulfonyl chloride which is directly reacted with L-alaninamide using K(2)CO(3) as base in aqueous DMF/THF to give 1 in a one-pot operation. The process was implemented for the production of 1 on a metric ton scale.

  DOI：

  10.1021/ol101960x