N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid | 1218780-26-7

• 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-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid
• 英文别名: 7-dodecyl-6-ethoxycarbonyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-8-carboxylic acid
• CAS: 1218780-26-7
• 化学式: C₂₃H₃₇NO₆
• 分子量: 423.55
• InChiKey: HDAJKVORNLMDOW-UHFFFAOYSA-N

物化性质

• 沸点：
  566.3±50.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid 在 N-碘代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 生成 ethyl 7-dodecyl-6-iodo-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-8-carboxylate
  参考文献：
  名称：

  Dioxypyrrole-Based Polymers via Dehalogenation Polycondensation Using Various Electrophilic Halogen Sources

  摘要：

  A convenient and efficient deiodination polycondensation method for the synthesis of dioxypyrrole-based (XDOP) polymers is reported. N-Halosuccinimides, iodine, and bromine were evaluated as halogenating agents to produce 2,5-halodioxypyrroles in situ via halodecarboxylation of 3,4-dioxypyrrole-2,5-dicarboxylic acids, which were then polymerized at 60 degrees C using dichloromethane or chloroform as solvent. When iodine and N-iodosuccinimide were employed as electrophilic halogen sources, the methodology produced macromolecules (M-n = 6.2-22.9 kDa) in satisfactory yields (55-71%) for two N-alkyl-3,4-dialkyloxypyrrole-based monomers that were tested. This method can be employed to produce a variety of XDOP-based homopolymers and regioregular copolymers starting from discrete oligomers under relatively mild reaction conditions.

  DOI：

  10.1021/ma300684t
• 作为产物：
  描述：

  diethyl N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2,5-dicarboxylate 在 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylic acid
  参考文献：
  名称：

  3,4-Propylenedioxypyrrole-Based Conjugated Oligomers via Pd-Mediated Decarboxylative Cross Coupling

  摘要：

  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.

  DOI：

  10.1021/ol100231g

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%.
• 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.
• Dioxypyrrole-Based Polymers via Dehalogenation Polycondensation Using Various Electrophilic Halogen Sources
  作者：Frank A. Arroyave、John R. Reynolds

  DOI：10.1021/ma300684t

  日期：2012.8.14

  A convenient and efficient deiodination polycondensation method for the synthesis of dioxypyrrole-based (XDOP) polymers is reported. N-Halosuccinimides, iodine, and bromine were evaluated as halogenating agents to produce 2,5-halodioxypyrroles in situ via halodecarboxylation of 3,4-dioxypyrrole-2,5-dicarboxylic acids, which were then polymerized at 60 degrees C using dichloromethane or chloroform as solvent. When iodine and N-iodosuccinimide were employed as electrophilic halogen sources, the methodology produced macromolecules (M-n = 6.2-22.9 kDa) in satisfactory yields (55-71%) for two N-alkyl-3,4-dialkyloxypyrrole-based monomers that were tested. This method can be employed to produce a variety of XDOP-based homopolymers and regioregular copolymers starting from discrete oligomers under relatively mild reaction conditions.