N-benzyl-2-formyl-3,4-ethylenedioxypyrrole | 376395-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-2-formyl-3,4-ethylenedioxypyrrole
• 英文别名: 6-Benzyl-2,3-dihydro-[1,4]dioxino[2,3-c]pyrrole-5-carbaldehyde
• CAS: 376395-17-4
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: KMXFUTAKPVQSKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-formyl-3,4-ethylenedioxypyrrole 在 potassium tert-butylate 、 氨 、 sodium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 6.0h， 生成 1-cyano-2-(2-(3,4-ethylenedioxypyrrolyl))-1-(2-thienyl)vinylene
  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：

  3,4-乙基二氧吡咯 在 sodium hydride 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.33h， 生成 N-benzyl-2-formyl-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

• 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：EP1465962B1

  公开（公告）日：2012-01-04
• US6791738B2
  申请人：——

  公开号：US6791738B2

  公开（公告）日：2004-09-14
• 3,4-Alkylenedioxypyrroles:  Functionalized Derivatives as Monomers for New Electron-Rich Conducting and Electroactive Polymers
  作者：Kyukwan Zong、John R. Reynolds

  DOI：10.1021/jo001620l

  日期：2001.10.1

  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.