8-[5-(6-carboxy-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrol-8-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-6-carboxylic acid | 1338533-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 8-[5-(6-carboxy-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrol-8-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-6-carboxylic acid
• CAS: 1338533-84-8
• 化学式: C₄₆H₆₈N₂O₁₀S
• 分子量: 841.119
• InChiKey: NZYCMMLDLFVGPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  59
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  potassium N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2,5-dicarboxylate 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 、 、 8-[5-(6-carboxy-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrol-8-yl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl]-7-dodecyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-c]pyrrole-6-carboxylic acid
  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

文献信息

• SYNTHESIS OF DIOXYHETEROCYCLE-BASED POLYMERS
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20130217801A1

  公开（公告）日：2013-08-22

  A method of polymerization for the preparation of conjugated polymers and copolymers comprising dioxypyrrole and/or dioxyfuran repeating units involves the halogen, N-haloimide, or N-haloamine promoted polymerization of monomers and/or oligomers comprising one or more dioxypyrrole and/or dioxyfuran units. The polymerization can be carried out over a wide range of temperatures and can be carried out with or without a solvent. The monomers allow the preparation of polymers having an oligomeric repeating unit comprising a conjugated unit other than a dioxypyrrole or dioxyfuran that is bound to two dioxypyrrole or dioxyfuran units.
• US9012600B2
  申请人：——

  公开号：US9012600B2

  公开（公告）日：2015-04-21
• 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.