2-ethynyl-1-methyl-4,5-diphenyl-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-ethynyl-1-methyl-4,5-diphenyl-1H-imidazole
• 英文别名: 2-Ethynyl-1-methyl-4,5-diphenylimidazole；2-ethynyl-1-methyl-4,5-diphenylimidazole
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: VKBXEOKFJJMYMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethynyl-1-methyl-4,5-diphenyl-1H-imidazole 在 copper(l) iodide 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.25h， 生成 4-(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)-1-[((S)-pyrrolidin-2-yl)methyl]-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings

  摘要：

  Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl) methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.019
• 作为产物：
  描述：

  1-methyl-4,5-diphenyl-1H-imidazole 3-oxide 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.83h， 生成 2-ethynyl-1-methyl-4,5-diphenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings

  摘要：

  Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl) methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.019

文献信息

• Tetrahydronaphthalinderivate und diese enthaltende Arzneimittel
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0268148B1

  公开（公告）日：1991-12-11