5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine-1,3-dicarboxylic acid | 202927-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine-1,3-dicarboxylic acid
• 英文别名: 5,10-dihydrothieno[3,4-c][2,5]benzodioxocine-1,3-dicarboxylic acid
• CAS: 202927-54-6
• 化学式: C₁₄H₁₀O₆S
• 分子量: 306.296
• InChiKey: WDNGIYILSXXDBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine-1,3-dicarboxylic acid 在 喹啉 、 copper chromite 作用下， 反应 8.0h， 以50%的产率得到5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine
  参考文献：
  名称：

  Preparation of an EDOT-based polymer: optoelectronic properties and electrochromic device application

  摘要：

  一个新型TPA/DTD电致变色器件的光谱电化学图。

  DOI：

  10.1039/c4ra13060j
• 作为产物：
  描述：

  3,4-二羟基噻吩-2,5-二甲酸二乙酯 在 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine-1,3-dicarboxylic acid
  参考文献：
  名称：

  Preparation of an EDOT-based polymer: optoelectronic properties and electrochromic device application

  摘要：

  一个新型TPA/DTD电致变色器件的光谱电化学图。

  DOI：

  10.1039/c4ra13060j

文献信息

• Diprotodecarboxylation Reactions of 3,4-Dialkoxythiophene-2,5-dicarboxylic Acids Mediated by Ag₂CO₃ and Microwaves
  作者：Pablo A. Cisneros-Pérez、Diego Martínez-Otero、Erick Cuevas-Yánez、Bernardo A. Uribe-Frontana

  DOI：10.1080/00397911.2013.800212

  日期：2014.1.17

  An efficient and rapid method is reported to obtain 3,4-dialkoxythiophenes from 3,4-dialkoxythiophene-2,5-dicarboxylic acids through a diprotodecarboxylation reaction with Ag2CO3/AcOH as a catalytic system and microwave heating in dimethylsulfoxide (DMSO) as solvent. This methodology lets us obtain for the first time good performance with thiophenes bearing strong electron-donating groups such as alkoxides. This methodology eliminates the usage of harmful quinoline as solvent, as well as the long reaction times typically used (12-18h) to obtain the 3,4-dialkoxythiophenes. The reaction of 7 diacids showed good yields (60-89%) following 20min of microwave heating in a temperature range of 120-150 degrees C. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]