1-(o-tolyl)-1,3-dihydro-2H-benzoimidazol-2-one | 1225535-04-5

• 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: 1-(o-tolyl)-1,3-dihydro-2H-benzoimidazol-2-one
• 英文别名: 1-(o-tolyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one；N-(2-methylphenyl)benzimidazol-2-one；3-(2-methylphenyl)-1H-benzimidazol-2-one
• CAS: 1225535-04-5
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: RHFREVRAPAZXTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(o-tolyl)-1,3-dihydro-2H-benzoimidazol-2-one 、 1,2-二溴乙烷 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 10.0h， 生成 1-(2-bromoethyl)-3-(o-tolyl)-1,3-dihydro-2H-benzo[d]imidazol-2-one
  参考文献：
  名称：

  Benzimidazolone-based serotonin 5-HT1A or 5-HT7R ligands: Synthesis and biological evaluation

  摘要：

  A new group of serotoninergic 5-HT1A or 5-HT7 receptor ligands was identified. These compounds were designed and synthesized on a benzimidazolone scaffold and they enrich the well-known arylpiperazine class of 5-HT ligands. Diverse pharmacomodulations induced a shift in the affinity and selectivity pro. le with final identification of new potent hits. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.008
• 作为产物：
  描述：

  C₁₉H₂₀N₂O₃ 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到1-(o-tolyl)-1,3-dihydro-2H-benzoimidazol-2-one
  参考文献：
  名称：

  Benzimidazolone-based serotonin 5-HT1A or 5-HT7R ligands: Synthesis and biological evaluation

  摘要：

  A new group of serotoninergic 5-HT1A or 5-HT7 receptor ligands was identified. These compounds were designed and synthesized on a benzimidazolone scaffold and they enrich the well-known arylpiperazine class of 5-HT ligands. Diverse pharmacomodulations induced a shift in the affinity and selectivity pro. le with final identification of new potent hits. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.008

文献信息

• Chan-Lam cross-coupling reaction based on the Cu 2 S/TMEDA system
  作者：Kateřina Janíková、Lukáš Jedinák、Tereza Volná、Petr Cankař

  DOI：10.1016/j.tet.2017.12.042

  日期：2018.2

  several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding

  基于Chan-Lam交叉偶联反应，开发了一种基于使用稳定铜（I）源的现成Cu 2 S / TMEDA系统的催化剂。用1 H-苯并[ d ]咪唑-2（3 H）-1，1 H-苯并[ d ]咪唑和1 H-咪唑以及缺电子，富电子和在室温下，在大气氧的存在下，对空间需求量高的硼酸，以中等至极好的收率得到交叉偶联的产物。另外，1 H-苯并[ d]的偶联反应]咪唑与几种频哪醇或新戊二醇硼酸酯表明该催化剂的进一步潜力。反应条件容许羟基和溴官能团。该催化体系还能够由伯脂族胺合成单-N-取代的苯胺。但是，仲胺和芳族胺的两种模型化合物哌啶和苯胺不会反应。两个空间要求的产品与受限Ç N键的旋转，通过将合成的Ñ 1的-arylation ħ -苯并[ d ]咪唑-2（3 H ^） -酮与ö-甲苯磺酸，能够确认由Chan-Lam交叉偶联反应制得的阻转异构体。此外，已经报道了一锅Chan-Lam和Suzuki-Miyaura反应的例子。
• Selenium‐Catalyzed Carbonylative Synthesis of 2‐Benzimidazolones from 2‐Nitroanilines with TFBen as the CO Source
  作者：Xinxin Qi、Rong Zhou、Jin‐Bao Peng、Jun Ying、Xiao‐Feng Wu

  DOI：10.1002/ejoc.201801739

  日期：2019.9

  A selenium‐catalyzed carbonylative reaction for the synthesis of 2‐benzimidazolones from 2‐nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene‐1,3,5‐triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2‐benzimidazolones were produced in moderate to excellent yields.

  已开发了一种硒催化的羰基化反应，用于从2-硝基苯胺合成2-苯并咪唑酮。在此策略中，为避免使用有毒的CO气体，TFBen（苯-1,3,5-三甲酸酯三甲酸酯）被用作固体和稳定的CO前体，并且生产了各种所需的2-苯并咪唑酮，其中中等至极好。产量。
• Benzimidazolone-based serotonin 5-HT1A or 5-HT7R ligands: Synthesis and biological evaluation
  作者：Eduard Badarau、Franck Suzenet、Andrzej J. Bojarski、Adriana-Luminiţa Fînaru、Gérald Guillaumet

  DOI：10.1016/j.bmcl.2009.02.008

  日期：2009.3

  A new group of serotoninergic 5-HT1A or 5-HT7 receptor ligands was identified. These compounds were designed and synthesized on a benzimidazolone scaffold and they enrich the well-known arylpiperazine class of 5-HT ligands. Diverse pharmacomodulations induced a shift in the affinity and selectivity pro. le with final identification of new potent hits. (C) 2009 Elsevier Ltd. All rights reserved.