3-diethylcarbamoyl-2-ethoxycarbonyl-4-phenylpyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-diethylcarbamoyl-2-ethoxycarbonyl-4-phenylpyrrole
• 英文别名: ethyl 3-(diethylcarbamoyl)-4-phenyl-1H-pyrrole-2-carboxylate
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: KRDIVIUYZDFWQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰基乙酸乙酯 、 N,N-diethyl-3-phenylpropiolamide 在 1,3-双(二苯基膦)丙烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以17%的产率得到3-diethylcarbamoyl-2-ethoxycarbonyl-4-phenylpyrrole
  参考文献：
  名称：

  Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst

  摘要：

  The copper-catalyzed reaction of isocyanides (CNCH(2)EWG(1)) 1 with electron-deficient alkynes (RC equivalent to CEWG(2)) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.

  DOI：

  10.1021/ja051875m

文献信息

• Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst
  作者：Shin Kamijo、Chikashi Kanazawa、Yoshinori Yamamoto

  DOI：10.1021/ja051875m

  日期：2005.6.1

  The copper-catalyzed reaction of isocyanides (CNCH(2)EWG(1)) 1 with electron-deficient alkynes (RC equivalent to CEWG(2)) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.