1-ethynyl-2-(hex-5-en-1-ynyl)-1H-imidazole | 874399-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-ethynyl-2-(hex-5-en-1-ynyl)-1H-imidazole
• 英文别名: 1-Ethynyl-2-hex-5-en-1-ynylimidazole；1-ethynyl-2-hex-5-en-1-ynylimidazole
• CAS: 874399-45-8
• 化学式: C₁₁H₁₀N₂
• 分子量: 170.214
• InChiKey: FCQKCSIBZCMBAF-UHFFFAOYSA-N

物化性质

• 沸点：
  300.9±35.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-ethynyl-2-(hex-5-en-1-ynyl)-1H-imidazole 、 六氟苯 反应 84.0h， 以72%的产率得到3,6-Diazatetracyclo[7.4.0.01,12.02,7]trideca-2,4,6,8-tetraene
  参考文献：
  名称：

  Intra- and intermolecular trapping of cyclopentapyrazine carbenes derived from 1,2-dialkynylimidazoles

  摘要：

  The thermolysis of 1,2-dialkynylimidazoles in benzene solution affords high yields of 7-pheiiyl-5H-cyclopentapyrazines, which presumably form by solvent trapping of cyclopentapyrazine carbene intermediates. In cases where dialkynylimidazole contains side chains that can participate in intramolecular carbene C-H insertion or olefin addition, these processes compete with solvent addition to afford novel tri- and tetracyclic pyrazines, which can be obtained in good yield when the thermolysis is carried out in hexafluoro benzene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.010
• 作为产物：
  描述：

  N-(2-trimethylsilyl)ethynyl-2-iodoimidazole 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 1-ethynyl-2-(hex-5-en-1-ynyl)-1H-imidazole
  参考文献：
  名称：

  Thermal cyclization of 1,2-dialkynylimidazoles to imidazo[1,2-a]pyridines

  摘要：

  Thermolysis of 1,2-dialkynylimidazoles in chlorinated solvents leads to 5-chloroimidazo[1,2-a]-pyridine products, which are also formed in DMF containing 1 equiv of HCI. Deuterium labeling of the starting dialkynylimidazoles indicates that reaction may proceed by multiple pathways, depending upon conditions and substituents. Dialkynylimidazoles can also give rise to 5-diethylamino-substituted imidazopyridines when the thermolysis is carried out in the presence of diethylamine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.084