N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid | 1338462-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid
• CAS: 1338462-84-2
• 化学式: C₂₀H₃₃NO₄
• 分子量: 351.486
• InChiKey: VWQUHEYKPPVYIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  25.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.69
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid 在 potassium hydrogencarbonate 、 bis(acetylacetonato)palladium(II) 、 三(邻甲基苯基)磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 43.0h， 以44%的产率得到4,7-bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrol-2-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles via Pd-Mediated Decarboxylative Cross-Coupling

  摘要：

  A general scheme for the synthesis of pi-conjugated molecules based on 3,4-dioxypyrroles is presented. The pi-conjugated molecules were synthesized via Pd-mediated decarboxylative cross-coupling using various 3,4-propylenedioxypyrrole carboxylic acids and aryl bromides, including the base-sensitive electron acceptor 4,7-dibromobenzo[c][1,2,5]-thiadiazole (BTD). N-Methylpyrrolidone was used as solvent, Pd(acac)(2) was employed as the palladium source and P(o-tol)(3) as the ligand. The methodology was applied to 3,4-dioxypyrrole monoacids and 3,4-dioxypyrrole diacids to produce multi-ring pi-conjugated systems containing phenyl, thiophenyl, BTD, and pyridinyl units. In general, the method has yielded a practical approach for the synthesis of 3,4-dioxypyrrole-based pi-conjugated molecules in acceptable to high yields of 44-94%.

  DOI：

  10.1021/jo201770j
• 作为产物：
  描述：

  N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid 在 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 120.0h， 生成 N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles via Pd-Mediated Decarboxylative Cross-Coupling

  摘要：

  A general scheme for the synthesis of pi-conjugated molecules based on 3,4-dioxypyrroles is presented. The pi-conjugated molecules were synthesized via Pd-mediated decarboxylative cross-coupling using various 3,4-propylenedioxypyrrole carboxylic acids and aryl bromides, including the base-sensitive electron acceptor 4,7-dibromobenzo[c][1,2,5]-thiadiazole (BTD). N-Methylpyrrolidone was used as solvent, Pd(acac)(2) was employed as the palladium source and P(o-tol)(3) as the ligand. The methodology was applied to 3,4-dioxypyrrole monoacids and 3,4-dioxypyrrole diacids to produce multi-ring pi-conjugated systems containing phenyl, thiophenyl, BTD, and pyridinyl units. In general, the method has yielded a practical approach for the synthesis of 3,4-dioxypyrrole-based pi-conjugated molecules in acceptable to high yields of 44-94%.

  DOI：

  10.1021/jo201770j