Dimethyl 7-cyanopyrrolo<1,2-b>pyrazin-5,6-dicarboxylat | 27425-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Dimethyl 7-cyanopyrrolo<1,2-b>pyrazin-5,6-dicarboxylat
• CAS: 27425-46-3
• 化学式: C₁₂H₉N₃O₄
• 分子量: 259.221
• InChiKey: QIUVIYMGEMEGFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.69
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 pyridazinium dicyanomethylide 以 乙腈 为溶剂， 反应 5.0h， 以95%的产率得到Dimethyl 7-cyanopyrrolo<1,2-b>pyrazin-5,6-dicarboxylat
  参考文献：
  名称：

  Water and Organic Synthesis: A Focus on the In-Water and On-Water Border. Reversal of the In-Water Breslow Hydrophobic Enhancement of the Normal endo-Effect on Crossing to On-Water Conditions for Huisgen Cycloadditions with Increasingly Insoluble Organic Liquid and Solid 2π-Dipolarophiles

  摘要：

  Measurements of the endo/exo product ratios for Huisgen cycloadditions with a series of vinyl ketones, alkyl acrylates, and substituted styrenes as dipolarophiles with phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles in acetonitrile and water show that as the reactions change from in-water (large hydrophobic enhancement of endo-products) to on-water, the hydrophobic enhancement of the endo-products is reduced and partially reversed (relative to acetonitrile). An expected increase of the endo-effect with increasing hydrophobic character of the dipolarophile is overcome by decreasing water solubility causing changeover to on-water conditions. On-water reactions do not show increased cycloaddition endo-effects (relative to organic solvents) as do in-water reactions.

  DOI：

  10.1021/jo400055g