5-benzhydryl-4-methyl-1H-imidazole | 86347-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzhydryl-4-methyl-1H-imidazole
• 英文别名: 4-benzhydryl-5-methyl-1H-imidazole
• CAS: 86347-10-6
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: VNVJVZFATHMEQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-甲基咪唑-4-甲醛 、 苯 在 三氟甲磺酸 作用下， 以99%的产率得到5-benzhydryl-4-methyl-1H-imidazole
  参考文献：
  名称：

  Superelectrophilic Chemistry of Imidazoles

  摘要：

  The mechanistic and synthetic chemistry of imidazole-based superelectrophiles has been studied. The protonated imidazole ring, or imidazolium group, is shown to enhance the electrophilic reactivity of an adjacent carboxonium group (compared to a related monocationic species). This leads to efficient condensation reactions between imidazole aldehydes and ketone with arenes in the Bronsted superacid CF3SO3H. The imidazole-based superelectrophiles are shown to be useful in other reactions leading to functionalized heterocycles. The imidazolium group may also trigger charge migration reactions in dicationic species.

  DOI：

  10.1021/jo802798x

文献信息

• Substituted imidazole derivatives and their preparation and use
  申请人：Farmos Group Ltd.

  公开号：EP0072615B1

  公开（公告）日：1985-12-27
• US4544664A
  申请人：——

  公开号：US4544664A

  公开（公告）日：1985-10-01
• US4639464A
  申请人：——

  公开号：US4639464A

  公开（公告）日：1987-01-27
• US4826864A
  申请人：——

  公开号：US4826864A

  公开（公告）日：1989-05-02
• Superelectrophilic Chemistry of Imidazoles
  作者：Matthew R. Sheets、Ang Li、Edward A. Bower、Andrew R. Weigel、Matthew P. Abbott、Robert M. Gallo、Adam A. Mitton、Douglas A. Klumpp

  DOI：10.1021/jo802798x

  日期：2009.3.20

  The mechanistic and synthetic chemistry of imidazole-based superelectrophiles has been studied. The protonated imidazole ring, or imidazolium group, is shown to enhance the electrophilic reactivity of an adjacent carboxonium group (compared to a related monocationic species). This leads to efficient condensation reactions between imidazole aldehydes and ketone with arenes in the Bronsted superacid CF3SO3H. The imidazole-based superelectrophiles are shown to be useful in other reactions leading to functionalized heterocycles. The imidazolium group may also trigger charge migration reactions in dicationic species.