4-[1-(4-(benzoyloxy)benzyl)-1H-benzimidazol-2-yl]phenylbenzoate | 1407156-93-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-[1-(4-(benzoyloxy)benzyl)-1H-benzimidazol-2-yl]phenylbenzoate
• 英文别名: [4-[[2-(4-Benzoyloxyphenyl)benzimidazol-1-yl]methyl]phenyl] benzoate；[4-[[2-(4-benzoyloxyphenyl)benzimidazol-1-yl]methyl]phenyl] benzoate
• CAS: 1407156-93-7
• 化学式: C₃₄H₂₄N₂O₄
• 分子量: 524.576
• InChiKey: LFDGOBYOTIPTBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲酰基苯甲酸苯酯 、 邻苯二胺 以 2,2,2-三氟乙醇 为溶剂， 反应 0.5h， 以92%的产率得到4-[1-(4-(benzoyloxy)benzyl)-1H-benzimidazol-2-yl]phenylbenzoate
  参考文献：
  名称：

  Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity

  摘要：

  Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.

  DOI：

  10.1021/jo301793z

文献信息

• Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity
  作者：Rajesh Chebolu、Damodara N. Kommi、Dinesh Kumar、Narendra Bollineni、Asit K. Chakraborti

  DOI：10.1021/jo301793z

  日期：2012.11.16

  Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1,2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1,2-disubstituted benzimidazoles at rt in short times. A mechanistic insight is invoked by NMR, mass spectrometry, and chemical studies to rationalize the selectivity. The ability of the fluorous alcohols in promoting the reaction and controlling the selectivity can be envisaged from their better hydrogen bond donor (HBD) abilities compared to that of the other organic solvents as well as of water. Due to the better HBD values, the fluorous alcohols efficiently promote the initial bisimine formation by electrophilic activation of the aldehyde carbonyl. Subsequently the hydrogen-bond-mediated activation of the in situ-formed bisimine triggers the rearrangement via 1,3-hydride shift to form the 1,2-disubstituted benzimidazoles.