2-Methyl-1-[(5-methylfuran-2-yl)-methyl]-1h-benzimidazole | 1494888-83-3

• 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: 2-Methyl-1-[(5-methylfuran-2-yl)-methyl]-1h-benzimidazole
• 英文别名: 2-methyl-1-[(5-methylfuran-2-yl)methyl]benzimidazole
• CAS: 1494888-83-3
• 化学式: C₁₄H₁₄N₂O
• mdl: MFCD23147876
• 分子量: 226.278
• InChiKey: NTUKZXRESCYHMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-1-[(5-methylfuran-2-yl)-methyl]-1h-benzimidazole 在 盐酸 作用下， 以 乙醇 为溶剂， 以59%的产率得到
  参考文献：
  名称：

  Synthesis of 2-Methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-Methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles

  摘要：

  A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H-benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening of the furan ring leading to the formation of a diketone fragment, which was then used for the formation of N-substituted pyrrole ring by the Paal-Knorr method. The effect of the nature of the amine on the cyclization was demonstrated.

  DOI：

  10.1007/s10593-013-1374-2
• 作为产物：
  描述：

  邻氨基乙酰苯胺 在 盐酸 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 苯 为溶剂， 生成 2-Methyl-1-[(5-methylfuran-2-yl)-methyl]-1h-benzimidazole
  参考文献：
  名称：

  Synthesis of 2-Methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-Methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles

  摘要：

  A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H-benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening of the furan ring leading to the formation of a diketone fragment, which was then used for the formation of N-substituted pyrrole ring by the Paal-Knorr method. The effect of the nature of the amine on the cyclization was demonstrated.

  DOI：

  10.1007/s10593-013-1374-2

文献信息

• Synthesis of 2-Methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-Methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles
  作者：T. A. Stroganova、V. M. Red’kin、G. A. Kovalenko、V. K. Vasilin、G. D. Krapivin

  DOI：10.1007/s10593-013-1374-2

  日期：2013.12

  A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H-benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening of the furan ring leading to the formation of a diketone fragment, which was then used for the formation of N-substituted pyrrole ring by the Paal-Knorr method. The effect of the nature of the amine on the cyclization was demonstrated.