ethyl (E)-3-bromo-3-(4,5,6,7-tetrahydro-1H-indol-2-yl)acrylate | 1257544-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl (E)-3-bromo-3-(4,5,6,7-tetrahydro-1H-indol-2-yl)acrylate
• CAS: 1257544-15-2
• 化学式: C₁₃H₁₆BrNO₂
• 分子量: 298.18
• InChiKey: CJRLRLVQZPDBSV-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4,5,6,7-四氢吲哚 、 3-溴丙酸乙酯 在 aluminum oxide 作用下， 反应 0.5h， 以54%的产率得到ethyl (E)-3-bromo-3-(4,5,6,7-tetrahydro-1H-indol-2-yl)acrylate
  参考文献：
  名称：

  Cross-coupling of 4,5,6,7-tetrahydroindole with functionalized haloacetylenes on active surfaces of metal oxides and salts

  摘要：

  Screening was performed of metal oxides (MgO, CaO, ZnO, BaO, Al(2)O(3), TiO(2), ZrO(2)) and salts (CaCO(3), K(2)CO(3), ZrSiO(4)) as active surfaces for the reaction of ethynylation of 4,5,6,7-tetrahydroindole with ethyl bromopropynoate and bromobenzoylacetylene. It was established that Ca, Mg, Zn, and Ba oxides assist the ethynylation of 4,5,6,7-tetrahydroindole, and their activity in the reaction with ethyl bromopropynoate considerably exceeds that of aluminum oxide. The ethynylation is accompanied with the formation of intermediate E-2-(1-bromoethenyl)-4,5,6,7-tetrahydroindole and side 1,1-di(4,5,6,7-tetrahydroindol-2-yl)ethenes and 1,1-di(4,5,6,7-tetrahydroindol-2-yl)bromoethanes.

  DOI：

  10.1134/s1070428010090186