(E)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide

• 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: (E)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide
• 英文别名: 3,5-dichloro-N-[(E)-2-(2-oxo-3H-benzimidazol-1-yl)-2-[4-(trifluoromethoxy)phenyl]ethenyl]-N-(2-phenylethyl)benzamide
• 化学式: C₃₁H₂₂Cl₂F₃N₃O₃
• 分子量: 612.435
• InChiKey: BKDOOSKOZHSUOB-TURZUDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide 反应 0.17h， 生成 (Z)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide
  参考文献：
  名称：

  (Z)-Stereoselective Synthesis ofMono- andBis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction

  摘要：

  Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.

  DOI：

  10.1021/acs.joc.5b00955
• 作为产物：
  描述：

  3,5-二氯苯甲酸 在 三氟乙酸 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 0.33h， 生成 (E)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide 、 (Z)-3,5-dichloro-N-(2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(4-(trifluoromethoxy)phenyl)vinyl)-N-phenethylbenzamide
  参考文献：
  名称：

  (Z)-Stereoselective Synthesis ofMono- andBis-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction

  摘要：

  Several novel cascade reactions are herein reported that enable access to a variety of unique mono- and bis-heterocyclic scaffolds. The sequence of cascade events are mediated through acid treatment of an Ugi adduct that affords 1,5-benzodiazepines which subsequently undergo an elegant rearrangement to deliver (E)-benzimidazolones, which through acid-promoted tautomerization convert to their corresponding (Z)-isomers. Moreover, a variety of heterocycles tethered to (Z)-benzimidazole-2-ones are also accessible through similar domino-like processes, demonstrating a general strategy to access significantly new scaffold diversity, each containing four points of potential diversification. Final structures of five scaffolds have been definitively proven by X-ray crystallography.

  DOI：

  10.1021/acs.joc.5b00955