3,4-丙烯基二氧基吡咯-2,5-二羧酸二乙酯 | 870704-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3,4-丙烯基二氧基吡咯-2,5-二羧酸二乙酯
• 英文名称: Diethyl 3,4-propylenedioxypyrrole-2,5-dicarboxylate
• 英文别名: diethyl 2,3,4,7-tetrahydro-[1,4]dioxepino[2,3-c]pyrrole-6,8-dicarboxylate
• CAS: 870704-20-4
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: OSXOFGHIVBAAEW-UHFFFAOYSA-N

物化性质

• 熔点：
  74.0-75.5 °C(lit.)
• 沸点：
  457.5±45.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26
• 危险类别码：
  R36

反应信息

• 作为反应物：
  描述：

  3,4-丙烯基二氧基吡咯-2,5-二羧酸二乙酯 在 potassium tert-butylate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 36.5h， 生成 potassium N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2,5-dicarboxylate
  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%.