diethyl 5,5'-(1,4-phenylene)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate) | 1218780-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 5,5'-(1,4-phenylene)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)phenyl]-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-6-carboxylate
• CAS: 1218780-28-9
• 化学式: C₅₀H₇₆N₂O₈
• 分子量: 833.162
• InChiKey: JCAXFMBISFECAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  60
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  99.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 5,5'-(1,4-phenylene)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate) 在 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 72.0h， 以92%的产率得到potassium 5,5'-(1,4-phenylene)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
• 作为产物：
  描述：

  在 2,2'-联吡啶 、 四(三苯基膦)钯 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 正庚烷 、 水 、 甲苯 为溶剂， 反应 42.0h， 生成 diethyl 5,5'-(1,4-phenylene)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

• 3,4-Propylenedioxypyrrole-Based Conjugated Oligomers <i>via</i> Pd-Mediated Decarboxylative Cross Coupling
  作者：Frank A. Arroyave、John R. Reynolds

  DOI：10.1021/ol100231g

  日期：2010.3.19

  An effective decarboxylative cross-coupling involving a 3,4-dioxypyrrole is reported. Several conjugated oligomers were synthesized in high yields using various aryl bromides. No copper salt or other transmetalating agent was required. The reaction conditions employed displayed relatively low sensitivity toward the presence of water.