dimethyl N-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate | 1144503-18-3

• 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 N-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate
• 英文别名: Dimethyl 1-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate；dimethyl 1-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate
• CAS: 1144503-18-3
• 化学式: C₂₇H₂₃NO₄
• 分子量: 425.484
• InChiKey: DJEBMVSUZVPSMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl N-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate 在 Pearlman's catalist 、 甲酸铵 作用下， 以 乙醇 为溶剂， 以100%的产率得到dimethyl 3,4-diphenyl-1H-pyrrole-2,5-dicarboxylate
  参考文献：
  名称：

  A General Method for the Synthesis of N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylates

  摘要：

  A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.

  DOI：

  10.3987/com-08-s(f)89
• 作为产物：
  描述：

  dimethyl N-benzyl-3,4-bis(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate 、 苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到dimethyl N-benzyl-3,4-diphenylpyrrole-2,5-dicarboxylate
  参考文献：
  名称：

  A General Method for the Synthesis of N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylates

  摘要：

  A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.

  DOI：

  10.3987/com-08-s(f)89

文献信息

• A General Method for the Synthesis of N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylates
  作者：Masatomo Iwao、Tsutomu Fukuda、Yukie Hayashida

  DOI：10.3987/com-08-s(f)89

  日期：——

  A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.