3-benzyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole | 1394843-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-benzyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole
• CAS: 1394843-50-5
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: XSKUONVSMTZHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯乙腈 、 5-azidopent-1-yne 在 gold(III) chloride 、 甲烷磺酸 作用下， 反应 8.0h， 以66%的产率得到3-benzyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole
  参考文献：
  名称：

  Synthesis of Bicyclic Imidazoles via [2 + 3] Cycloaddition between Nitriles and Regioselectively Generated α-Imino Gold Carbene Intermediates

  摘要：

  The cyclic alpha-imino gold carbene intermediate B is most likely generated in situ via regioselective nitrene transfer from an azido group to a tethered terminal alkyne in the presence of a gold catalyst and at ambient temperature. This highly electrophilic intermediate can react with a weakly nucleophilic nitrile, which is used as the reaction solvent, to deliver a bicyclic imidazole rapidly in an overall bimolecular [2 + 2 + 1] cycloaddition and in mostly serviceable yield. The competing intramolecular Huisgen reaction, although likely also catalyzed by gold, is minimized by using AuCl3 as the catalyst.

  DOI：

  10.1021/ol302102h