N-benzyl-3,4-ethylenedioxypyrrole | 376395-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-3,4-ethylenedioxypyrrole
• 英文别名: 6-benzyl-3,6-dihydro-2H-[1,4]dioxino[2,3-c]pyrrole；6-Benzyl-2,3-dihydro-[1,4]dioxino[2,3-c]pyrrole
• CAS: 376395-16-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: KRRSHRMPBOCZJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3,4-ethylenedioxypyrrole 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 3.0h， 生成 (E)-3-(6-benzyl-2,3-dihydro-[1,4]dioxino[2,3-c]pyrrol-5-yl)-2-thiophen-2-ylprop-2-enenitrile
  参考文献：
  名称：

  3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers

  摘要：

  New functionalized derivatives of 3,4-ethylenedioxypyrrole (EDOP, 5a) and 3,4-(1,3-propylenedioxy)-pyrrole (ProDOP, 5b) as especially electron-rich monomers which yield highly electroactive and stable conducting polymers useful for a diverse set Of applications have been synthesized. N-Alkylations of ProDOP were carried out to yield a variety of ProDOP derivatives having alkyl, sulfonatoalkoxy, glyme, and glyme alcohol pendant chains. Iodization of EDOP and ProDOP via iodo-decarboxylation afforded iodo-functionalized derivatives useful for subsequent aryl coupling chemistry. N-Protection and formylation of EDOP, followed by Knoevenagel condensation of the resultant 2-formyl-EDOP with aryl acetonitrile derivatives, led to 1-cyano-2-(2-(3,4-ethylenedioxy-pyrryl))-1-(2-thienyl)vinylene (23) (Th-CNV-EDOP) and 1-cyano-2-(2-(3,4-ethylenedioxypyrryl))-1-(2-(3,4-ethylenedioxythienyl)vinylene (26) (EDOT-CNV-EDOP). A 14-crown-4-ether 34 based dioxypyrrole was synthesized with a cavity potentially useful for lithium ion coordination and sensing in the resultant electroactive polymer. C-Alkylated ProDOPs (43a, 43b, and 43c) containing octyl, ethylhexyl, and dioctyl substituents appended to the central methylene of the propylene bridge, were prepared as monomers for potentially soluble pi -conjugated polymers.

  DOI：

  10.1021/jo001620l
• 作为产物：
  描述：

  dimethyl 1-benzyl-3,4-ethylenedioxypyrrole-2,5-dicarboxylate 在 sodium hydroxide 、 三乙醇胺 作用下， 以 乙醇 、 水 为溶剂， 反应 6.17h， 生成 N-benzyl-3,4-ethylenedioxypyrrole
  参考文献：
  名称：

  3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers

  摘要：

  New functionalized derivatives of 3,4-ethylenedioxypyrrole (EDOP, 5a) and 3,4-(1,3-propylenedioxy)-pyrrole (ProDOP, 5b) as especially electron-rich monomers which yield highly electroactive and stable conducting polymers useful for a diverse set Of applications have been synthesized. N-Alkylations of ProDOP were carried out to yield a variety of ProDOP derivatives having alkyl, sulfonatoalkoxy, glyme, and glyme alcohol pendant chains. Iodization of EDOP and ProDOP via iodo-decarboxylation afforded iodo-functionalized derivatives useful for subsequent aryl coupling chemistry. N-Protection and formylation of EDOP, followed by Knoevenagel condensation of the resultant 2-formyl-EDOP with aryl acetonitrile derivatives, led to 1-cyano-2-(2-(3,4-ethylenedioxy-pyrryl))-1-(2-thienyl)vinylene (23) (Th-CNV-EDOP) and 1-cyano-2-(2-(3,4-ethylenedioxypyrryl))-1-(2-(3,4-ethylenedioxythienyl)vinylene (26) (EDOT-CNV-EDOP). A 14-crown-4-ether 34 based dioxypyrrole was synthesized with a cavity potentially useful for lithium ion coordination and sensing in the resultant electroactive polymer. C-Alkylated ProDOPs (43a, 43b, and 43c) containing octyl, ethylhexyl, and dioctyl substituents appended to the central methylene of the propylene bridge, were prepared as monomers for potentially soluble pi -conjugated polymers.

  DOI：

  10.1021/jo001620l

文献信息

• 3,4-Ethylenedioxypyrrole (EDOP) Monomers with Aromatic Substituents for Parahydrophobic Surfaces by Electropolymerization
  作者：Claudio Mortier、Thierry Darmanin、Frédéric Guittard

  DOI：10.1021/acs.macromol.5b01054

  日期：2015.8.11

  properties through the electropolymerization of 3,4-ethylenedioxypyrrole (EDOP) derivatives. We report for the first time an electrochemical study of EDOP derivatives bearing aromatic cycles (phenyl, naphthalene, biphenyl, and pyrene). Eight novel EDOP monomers are studied with and without the presence of an ethyl acetate spacer in order to give more mobility to the aromatic substituents. Surprinsgly, higher

  在自然界中，例如荷叶和红玫瑰中存在超疏水性（低附着力）和副疏水性（高附着力）特性。例如，水粘附力的控制对于集水应用极为重要。在这里，我们报告通过3,4-乙二氧基吡咯（EDOP）衍生物的电聚合获得对疏水性。我们首次报道了带有芳香环（苯基，萘，联苯和pyr）的EDOP衍生物的电化学研究。在有或没有乙酸乙酯间隔基的情况下，研究了八种新的EDOP单体，以赋予芳族取代基更多的迁移率。令人惊讶的是，在用间隔物进行电聚合的过程中观察到更高的空间位阻。但是，这些聚合物更不溶于间隔基，这是电聚合的重要点。用联苯基和间隔基获得最高的对疏水性能，这是由于存在微观结构和纳米结构。
• Electrochromic polymers and polymer electrochromic devices
  申请人：University of Florida

  公开号：US20030174377A1

  公开（公告）日：2003-09-18

  The subject invention pertains to electrochromic polymers and polymer electrochromic devices. In a specific embodiment, two complementary polymers can be matched and incorporated into dual polymer electrochromic devices. The anodically coloring polymers in accordance with the subject invention can allow control over the color, brightness, and environmental stability of an electrochromic window. In addition, high device contrast ratios, high transmittance changes, and high luminance changes can be achieved, along with half-second switching times for full color change. Also provided are electrochromic devices such as advertising signage, video monitors, stadium scoreboards, computers, announcement boards, warning systems for cell phones, warning/information systems for automobiles, greeting cards, electrochromic windows, billboards, electronic books, and electrical wiring. The subject invention also provides for the use of complementary electrochromic polymers in the manufacture of electrochromic devices. In some embodiments, the devices of the invention can be prepared using metal vapor deposition or line patterning.

  本发明涉及电致变色聚合物和聚合物电致变色器件。在一个特定的实施例中，可以将两种互补的聚合物配对并纳入双聚合物电致变色器件中。根据本发明的阳极着色聚合物可以允许控制电致变色窗户的颜色、亮度和环境稳定性。此外，可以实现高对比度比、高透射率变化和高亮度变化，以及半秒钟的全彩色变换时间。还提供了电致变色器件，例如广告标志、视频监视器、体育场记分牌、计算机、公告牌、手机警告系统、汽车警告/信息系统、贺卡、电致变色窗户、广告牌、电子书和电气布线。本发明还提供了在制造电致变色器件时使用互补电致变色聚合物的方法。在一些实施例中，可以使用金属蒸汽沉积或线路图案制备本发明的器件。
• ELECTROCHROMIC POLYMERS AND POLYMER ELECTROCHROMIC DEVICES
  申请人：University of Florida

  公开号：EP1465962A1

  公开（公告）日：2004-10-13
• US6791738B2
  申请人：——

  公开号：US6791738B2

  公开（公告）日：2004-09-14
• [EN] ELECTROCHROMIC POLYMERS AND POLYMER ELECTROCHROMIC DEVICES<br/>[FR] POLYMERES ELECTROCHROMIQUES ET DISPOSITIFS ELECTROCHROMIQUES POLYMERIQUES
  申请人：UNIV FLORIDA

  公开号：WO2003046106A1

  公开（公告）日：2003-06-05

  The subject invention pertains to electrochromic polymers and polymer electrochromic devices. In a specific embodiment, two complementary polymers can be matched and incorporated into dual polymer electrochromic devices. The anodically coloring polymers in accordance with the subject invention can allow control over the color, brightness, and environmental stability of an electrochromic window. In addition, high device contrast ratios, high transmittance changes, and high luminance changes can be achieved, along with half-second switching times for full color change. Also provided are electrochromic devices such as advertising signage, video monitors, stadium scoreboards, computers, announcement boards, warning systems for cell phones, warning/information systems for automobiles, greeting cards, electrochromic windows, billboards, electronic books, and electrical wiring. The subject invention also provides for the use of complementary electrochromic polymers in the manufacture of electrochromic devices. In some embodiments, the devices of the invention can be prepared using metal vapor deposition or line patterning.