diethyl 5,5'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate) | 1338463-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: diethyl 5,5'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate)
• 英文别名: ethyl 7-dodecyl-8-[4-(7-dodecyl-6-ethoxycarbonyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrol-8-yl)-2,1,3-benzothiadiazol-7-yl]-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-6-carboxylate
• CAS: 1338463-03-8
• 化学式: C₅₀H₇₄N₄O₈S
• 分子量: 891.226
• InChiKey: RTWCDFKWUROYMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  63
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid 在 bis(acetylacetonato)palladium(II) 、 potassium hydrogencarbonate 、 三(邻甲基苯基)磷 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以94%的产率得到diethyl 5,5'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate)
  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

文献信息

• Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles <i>via</i> Pd-Mediated Decarboxylative Cross-Coupling
  作者：Frank A. Arroyave、John R. Reynolds

  DOI：10.1021/jo201770j

  日期：2011.11.4

  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%.