3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitrile | 150008-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitrile
• 英文别名: 3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxobenzimidazole-1-carbonitrile
• CAS: 150008-62-1
• 化学式: C₁₁H₉N₅O
• 分子量: 227.225
• InChiKey: BCZHTWBPLXOSIL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±25.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitrile 在 盐酸 、 sodium hydroxide 、 sodium carbonate 作用下， 反应 24.0h， 以23%的产率得到1-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole
  参考文献：
  名称：

  Synthesis and Transformations of 2-Amino-1-(4,5-Dihydro-1H-imidazol-2-yl)benzimidazoles. A Route to 2,3-Dihydrobenzo[4,5]imidazo[1,2-c]imidazo[1,2-a][1,3,5]triazine Ring System

  摘要：

  Starting from 3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitriles (la-e) the 2-amino-1-(4,5-dihydro-1H-imidazol-2-yl)benzimidazoles (2a-e) and 1-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazoles (3a-e) have been synthesized. Cyclocondensation of 2a with acetic anhydride or acyl chlorides gave novel functionalized 2,3-dihydrobenzo[4,5]imidazo[1,2-c]imidazo[1,2-a]triazines (4a-d).

  DOI：

  10.3987/com-98-8222
• 作为产物：
  描述：

  溴化氰 、 N-(4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydroxylamine hydrochloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitrile
  参考文献：
  名称：

  串联1,4-二氮杂，3-oxa-Cope重排-亲核加成反应。通往2-oxobenzimidazoles的途径。

  摘要：

  已经进行了一种新颖的串联1,4-二氮杂-3-氧杂-Cope重排-亲核加成反应，其中在N-的初始[3,3]σ重排的基础上合理化了2-oxobenzimidazoles的形成。氰基苯胺，然后在中间异氰酸酯中进行分子内亲核加成。

  DOI：

  10.1016/s0040-4039(00)73577-5

文献信息

• Tandem 1,4-diaza,3-oxa-Cope rearrangement - nucleophilic addition reaction. A route to 2-oxobenzimidazoles.
  作者：Franciszek Saczewski、Tomasz Debowski

  DOI：10.1016/s0040-4039(00)73577-5

  日期：1993.4

  A novel tandem 1,4-diaza-3-oxa-Cope rearrangement - nucleophilic addition reaction has been deviced in which the formation of 2-oxobenzimidazoles has been rationalized on the basis of an initial [3,3]sigmatropic rearrangment of the N-cyanato-anilines , followed by an intramolecular nucleophilic addition in the intermediate isocyanates .

  已经进行了一种新颖的串联1,4-二氮杂-3-氧杂-Cope重排-亲核加成反应，其中在N-的初始[3,3]σ重排的基础上合理化了2-oxobenzimidazoles的形成。氰基苯胺，然后在中间异氰酸酯中进行分子内亲核加成。
• Synthesis and Transformations of 2-Amino-1-(4,5-Dihydro-1H-imidazol-2-yl)benzimidazoles. A Route to 2,3-Dihydrobenzo[4,5]imidazo[1,2-c]imidazo[1,2-a][1,3,5]triazine Ring System
  作者：Franciszek Saczewski、Tomasz Debowski、Jacek Szmigiel

  DOI：10.3987/com-98-8222

  日期：——

  Starting from 3-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazole-1-carbonitriles (la-e) the 2-amino-1-(4,5-dihydro-1H-imidazol-2-yl)benzimidazoles (2a-e) and 1-(4,5-dihydro-1H-imidazol-2-yl)-2-oxo-2,3-dihydrobenzimidazoles (3a-e) have been synthesized. Cyclocondensation of 2a with acetic anhydride or acyl chlorides gave novel functionalized 2,3-dihydrobenzo[4,5]imidazo[1,2-c]imidazo[1,2-a]triazines (4a-d).
• Synthesis, Structure, and Biological Activities of SomeN-(4,5-Dihydro-1H-imidazol-2-yl)-l,3-dihydrobenzimidazole Derivatives
  作者：Franciszek Sączewski、Tomasz Debowski、Jacek Petrusewicz、Henryk Trzeciak、Ewa Krzystanek、Marak Krzystanek、Maria Gdaniec、Emilia Novakowska

  DOI：10.1002/(sici)1521-4184(199807)331:7/8<241::aid-ardp241>3.0.co;2-6

  日期：1998.7

  A series of novel N-(4,5-dihydroimidazol-2-yl)-1,3-dihydrobenzimidazole derivatives 2a-d, 3a-d and 4a-p were prepared and their structure was determined by IR and NMR spectroscopic data as well as X-ray analysis of carbonitrile 2a. The compounds were studied as potential inhibitors of the human blood platelet aggregation induced by adrenaline or ADP. Compounds of type 3 proved efficacious for the reduction of arterial blood pressure upon intravenous administration to normotensive rats.