bis(1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol | 380892-07-9

• 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: bis(1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol
• 英文别名: bis(1-methyl-1H-benzimidazol-2-yl)(phenyl)methanol；bis(1-methylbenzimidazol-2-yl)-phenylmethanol
• CAS: 380892-07-9
• 化学式: C₂₃H₂₀N₄O
• 分子量: 368.438
• InChiKey: VCNVRFKYHNHSNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol 在 三氟甲磺酸 作用下， 以91%的产率得到1-methyl-9-(1-methyl-1H-benzimidazol-2-yl)-1H-benzimidazo[1,2-a]indole
  参考文献：
  名称：

  Charge Delocalization and Enhanced Acidity in Tricationic Superelectrophiles

  摘要：

  This Article presents the results from studies related to the chemistry of tricationic superelectrophiles. A series of triaryl methanols were ionized in Bronsted superacids, and the corresponding tricationic intermediates were formed. The trications are found to participate in two types of reactions; both are characteristic of highly charged organic cations. One set of reactions occurs through charge migration. A second set of reactions occurs through deprotonation of an unusually acidic site on the tricationic species. One of the tricationic intermediates has been directly observed by low temperature NMR spectroscopy. These highly charged ions and their reactions have also been studied using density functional theory calculations. As a result of charge migration, electron density at a carbocation site is found to increase with progression from monocationic to pentacationic structures.

  DOI：

  10.1021/ja2046364
• 作为产物：
  描述：

  苯甲酸甲酯 、 1-甲基苯并咪唑 在 正丁基锂 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 bis(1-methyl-1H-benzo[d]imidazol-2-yl)(phenyl)methanol
  参考文献：
  名称：

  Charge Delocalization and Enhanced Acidity in Tricationic Superelectrophiles

  摘要：

  This Article presents the results from studies related to the chemistry of tricationic superelectrophiles. A series of triaryl methanols were ionized in Bronsted superacids, and the corresponding tricationic intermediates were formed. The trications are found to participate in two types of reactions; both are characteristic of highly charged organic cations. One set of reactions occurs through charge migration. A second set of reactions occurs through deprotonation of an unusually acidic site on the tricationic species. One of the tricationic intermediates has been directly observed by low temperature NMR spectroscopy. These highly charged ions and their reactions have also been studied using density functional theory calculations. As a result of charge migration, electron density at a carbocation site is found to increase with progression from monocationic to pentacationic structures.

  DOI：

  10.1021/ja2046364

文献信息

• Charge Delocalization and Enhanced Acidity in Tricationic Superelectrophiles
  作者：Rajasekhar Reddy Naredla、Chong Zheng、Sten O. Nilsson Lill、Douglas A. Klumpp

  DOI：10.1021/ja2046364

  日期：2011.8.24

  This Article presents the results from studies related to the chemistry of tricationic superelectrophiles. A series of triaryl methanols were ionized in Bronsted superacids, and the corresponding tricationic intermediates were formed. The trications are found to participate in two types of reactions; both are characteristic of highly charged organic cations. One set of reactions occurs through charge migration. A second set of reactions occurs through deprotonation of an unusually acidic site on the tricationic species. One of the tricationic intermediates has been directly observed by low temperature NMR spectroscopy. These highly charged ions and their reactions have also been studied using density functional theory calculations. As a result of charge migration, electron density at a carbocation site is found to increase with progression from monocationic to pentacationic structures.