(Z)-5-<(2-amino-4,5-dichlorophenyl)methylene>imidazolidine-2,4-dione | 175918-55-5

• 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: (Z)-5-<(2-amino-4,5-dichlorophenyl)methylene>imidazolidine-2,4-dione
• 英文别名: Z-5-<(2-amino-4,5-dichlorophenyl)methylene>imidazolidin-2,4-dione；(5Z)-5-[(2-amino-4,5-dichlorophenyl)methylidene]imidazolidine-2,4-dione
• CAS: 175918-55-5
• 化学式: C₁₀H₇Cl₂N₃O₂
• 分子量: 272.09
• InChiKey: IMGVGHNXHMBYMV-WAPJZHGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-<(2-amino-4,5-dichlorophenyl)methylene>imidazolidine-2,4-dione 在 ammonium hydroxide 、 四氯化锡 、 copper(II) sulfate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 69.0h， 生成 6,7-dichloro-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo<4,5-b>quinolin-2-one
  参考文献：
  名称：

  Synthesis and Regioselective Ribosylation of 6,7-Dichloroimidazo[4,5-b]quinolin-2-one

  摘要：

  The polyhalogenated benzimidazole nucleosides 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) and the 2-bromo analogue (BDCRB) were synthesized in our laboratory and established as potent and selective antiviral agents against human cytomegalovirus (HCMV) with a novel mode of action. In an effort to study the behavior of the key substructure of these analogues in a dimensionally stretched-out manner and probe the spatial limitation of the target enzyme(s), a series of N1- and N3-ribonucleosides of imidazo[4,5-b]quinolines were designed as linear dimensional analogues. The nucleosides 6,7-dichloro-1-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one and 6,7-dichloro-3-(beta-D-ribofuranosyl)imidazo[4,5-b]quinolin-2-one were selected and prepared as the key intermediates in this study. During this study, a novel photoassisted annulation was developed for the synthesis of 6,7-dichloroimidazo[4,5-b]quinolin-2-one, which overcame several problems that were encountered with the literature annulation method. Regioselective ribosylations of this heterocycle were developed and gave both the N1 and the N3 isomers in high yield.

  DOI：

  10.1021/jo982084o
• 作为产物：
  描述：

  4,5-二氯-2-硝基苯甲醛 在 铁粉 、 iron(II) sulfate 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 (Z)-5-<(2-amino-4,5-dichlorophenyl)methylene>imidazolidine-2,4-dione
  参考文献：
  名称：

  新型光辅助环化反应合成6,7-二氯咪唑并[4,5-b]喹啉-2-酮

  摘要：

  开发了一种新型的光辅助环用于合成6,7-二氯咪唑并[4,5-b]喹啉-2-酮。这种温和的闭环方法避免了与以前的方法有关的问题，应该可以耐受各种官能团。

  DOI：

  10.1016/0040-4039(96)00308-5