ethyl 1-(adamantan-1-yl)-5-methyl-3-oxido-1H-imidazole-4-carboxylate | 1310826-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(adamantan-1-yl)-5-methyl-3-oxido-1H-imidazole-4-carboxylate
• CAS: 1310826-07-3
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: YEWYLSHVIQDCBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  58.17
• 氢给体数：
  0.0
• 氢受体数：
  4.0

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 、 ethyl 1-(adamantan-1-yl)-5-methyl-3-oxido-1H-imidazole-4-carboxylate 以 氯仿 为溶剂， 以64%的产率得到ethyl 1-(adamantan-1-yl)-5-methylimidazole-4-carboxylate
  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：

  N-methylidene adamantan-1-amine 、 2-(羟亚氨基)乙酰乙酸乙酯 以 溶剂黄146 为溶剂， 反应 24.0h， 以34%的产率得到ethyl 1-(adamantan-1-yl)-5-methyl-3-oxido-1H-imidazole-4-carboxylate
  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