2-(furan-2-yl)-4-(4-(4-methoxyphenyl)-2-oxo-2,5-dihydro-1Hbenzo[b][1,4]diazepin-3-yl)-4,5-dihydro-3H-benzo[e][1,4]diazepin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2-(furan-2-yl)-4-(4-(4-methoxyphenyl)-2-oxo-2,5-dihydro-1Hbenzo[b][1,4]diazepin-3-yl)-4,5-dihydro-3H-benzo[e][1,4]diazepin-3-one
• 英文别名: 2-(furan-2-yl)-4-[4-(4-methoxyphenyl)-2-oxo-1,5-dihydro-1,5-benzodiazepin-3-yl]-5H-1,4-benzodiazepin-3-one
• 化学式: C₂₉H₂₂N₄O₄
• 分子量: 490.518
• InChiKey: IHFVYTIRGUEFAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(furan-2-yl)-4-(4-(4-methoxyphenyl)-2-oxo-2,5-dihydro-1Hbenzo[b][1,4]diazepin-3-yl)-4,5-dihydro-3H-benzo[e][1,4]diazepin-3-one 反应 0.17h， 以94%的产率得到(Z)-2-(furan-2-yl)-4-(2-(4-methoxyphenyl)-2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)vinyl)-4,5-dihydro-3H-benzo[e][1,4]-diazepin-3-one
  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：

  α-氧代-2-呋喃乙酸 在 三氟乙酸 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 2-(furan-2-yl)-4-(4-(4-methoxyphenyl)-2-oxo-2,5-dihydro-1Hbenzo[b][1,4]diazepin-3-yl)-4,5-dihydro-3H-benzo[e][1,4]diazepin-3-one
  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

文献信息

• (<i>Z</i>)-Stereoselective Synthesis of<i>Mono</i>- and<i>Bis</i>-heterocyclic Benzimidazol-2-ones via Cascade Processes Coupled with the Ugi Multicomponent Reaction
  作者：Zhigang Xu、Guillermo Martinez-Ariza、Alexandra P. Cappelli、Sue A. Roberts、Christopher Hulme

  DOI：10.1021/acs.joc.5b00955

  日期：2015.9.18

  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.