4-[[(5R)-7-(3,5-dichlorophenyl)-5-methyl-3,6-dioxo-2H-imidazo[1,2-a]imidazol-5-yl]methyl]benzonitrile | 835917-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-[[(5R)-7-(3,5-dichlorophenyl)-5-methyl-3,6-dioxo-2H-imidazo[1,2-a]imidazol-5-yl]methyl]benzonitrile
• CAS: 835917-16-3
• 化学式: C₂₀H₁₄Cl₂N₄O₂
• 分子量: 413.263
• InChiKey: WRGLFEWLKFYBDQ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[[(5R)-7-(3,5-dichlorophenyl)-5-methyl-3,6-dioxo-2H-imidazo[1,2-a]imidazol-5-yl]methyl]benzonitrile 在 三甲基氯硅烷 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 4-[[(5R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-3-piperazin-1-ylsulfonylimidazo[1,2-a]imidazol-5-yl]methyl]benzonitrile
  参考文献：
  名称：

  A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of thiohydantoins

  摘要：

  An efficient and chromatography-free approach for synthesis of a new class of LFA- I inhibitor was developed. A copper(I) chloride-promoted intramolecular cyclization of thiohydantoins 7a-b serves as a key step to highly functionalized bicyclic guanidines 5a-b, that were subsequently converted to H-imidazol[l,2-a]imidazol-2-one LFA-1 inhibitors. This process has been successfully implemented in the pilot plant to produce multikilogram quantities of LFA-1 inhibitors such as la-b. (C) 2004 Elsevier Ltd. All ri.-hts reserved

  DOI：

  10.1016/j.tetlet.2004.11.065
• 作为产物：
  描述：

  4-[[(2R,4R)-1-(3,5-dichlorophenyl)-4-methyl-5-oxo-2-propan-2-yl-3-(2,2,2-trifluoroacetyl)imidazolidin-4-yl]methyl]benzonitrile 在 sodium hydroxide 、 Celite 、 三甲基乙酰氯 、 苄基三甲基氢氧化铵 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 4-[[(5R)-7-(3,5-dichlorophenyl)-5-methyl-3,6-dioxo-2H-imidazo[1,2-a]imidazol-5-yl]methyl]benzonitrile
  参考文献：
  名称：

  A practical synthesis of LFA-1 inhibitors utilizing CuCl-promoted intramolecular cyclization of thiohydantoins

  摘要：

  An efficient and chromatography-free approach for synthesis of a new class of LFA- I inhibitor was developed. A copper(I) chloride-promoted intramolecular cyclization of thiohydantoins 7a-b serves as a key step to highly functionalized bicyclic guanidines 5a-b, that were subsequently converted to H-imidazol[l,2-a]imidazol-2-one LFA-1 inhibitors. This process has been successfully implemented in the pilot plant to produce multikilogram quantities of LFA-1 inhibitors such as la-b. (C) 2004 Elsevier Ltd. All ri.-hts reserved

  DOI：

  10.1016/j.tetlet.2004.11.065