4-acetyl-1-benzyl-5-methyl-1H-imidazole 3-oxide | 1310826-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-1-benzyl-5-methyl-1H-imidazole 3-oxide
• CAS: 1310826-04-0
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: PZFVBFJDXDCLDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  48.94
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2,4,4-四甲基-1,3-环丁烷二硫酮 、 4-acetyl-1-benzyl-5-methyl-1H-imidazole 3-oxide 以 氯仿 为溶剂， 以72%的产率得到4-acetyl-1-benzyl-5-methylimidazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis of New Imidazole 3-Oxides; Unexpected Deoxygenation of Some Derivatives in the Reaction with 2,2,4,4-Tetramethylcyclobutane-1,3-dithione

  摘要：

  Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)-5-methylimidazole 3-oxide. It was shown that the presence of an electron-withdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.

  DOI：

  10.3987/com-10-12130
• 作为产物：
  描述：

  1,3,5-三苄基六氢-1,3,5-三嗪 、 2,3,4-戊三酮肟 (6ci,7ci,8ci,9ci) 以 乙醚 为溶剂， 以57%的产率得到4-acetyl-1-benzyl-5-methyl-1H-imidazole 3-oxide
  参考文献：
  名称：

  Synthesis of New Imidazole 3-Oxides; Unexpected Deoxygenation of Some Derivatives in the Reaction with 2,2,4,4-Tetramethylcyclobutane-1,3-dithione

  摘要：

  Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)-5-methylimidazole 3-oxide. It was shown that the presence of an electron-withdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.

  DOI：

  10.3987/com-10-12130