diethyl (5-formylthiophen-2-yl)methylphosphonate | 362526-27-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (5-formylthiophen-2-yl)methylphosphonate
• 英文别名: diethyl 5-formyl-2-thienylmethylphosphonate；Diethyl [(5-Formyl-2-thienyl)methyl]phosphonate；5-(diethoxyphosphorylmethyl)thiophene-2-carbaldehyde
• CAS: 362526-27-0
• 化学式: C₁₀H₁₅O₄PS
• 分子量: 262.266
• InChiKey: IHJYJYBHUWZJHV-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±37.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (5-formylthiophen-2-yl)methylphosphonate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 5-[(E)-2-[5-(4-hydroxypiperidin-1-yl)thiophen-2-yl]ethenyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  FORMYLATION OF DIETHYL 2-THIENYLMETHYLPHOSPHONATE FOR ONE-POT SYNTHESIS OF AMINOTHIENOSTILBENECARBOXALDEHYDE

  摘要：

  Diethyl 5-formyl-2-thienylmethylphosphonate is synthesized via the formylation of 2-thienylmethylphosphonate, and has been demonstrated to be an efficient intermediate thienylvinylene elongation of electron-rich conjugate systems.

  DOI：

  10.1081/scc-100104045
• 作为产物：
  描述：

  2-(噻吩甲基)膦酸二乙酯 、 1,1-二氯甲醚 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到diethyl (5-formylthiophen-2-yl)methylphosphonate
  参考文献：
  名称：

  FORMYLATION OF DIETHYL 2-THIENYLMETHYLPHOSPHONATE FOR ONE-POT SYNTHESIS OF AMINOTHIENOSTILBENECARBOXALDEHYDE

  摘要：

  Diethyl 5-formyl-2-thienylmethylphosphonate is synthesized via the formylation of 2-thienylmethylphosphonate, and has been demonstrated to be an efficient intermediate thienylvinylene elongation of electron-rich conjugate systems.

  DOI：

  10.1081/scc-100104045

文献信息

• Synthesis and Photovoltaic Properties of Efficient Organic Dyes Containing the Benzo[<i>b</i>]furan Moiety for Solar Cells
  作者：Il Jung、Jae Kwan Lee、Kyu Ho Song、Kihyung Song、Sang Ook Kang、Jaejung Ko

  DOI：10.1021/jo0625150

  日期：2007.5.1

  New organic dyes composed of the benzo[b]furan donor, thiophene-conjugated bridge, and cyano acrylic acid acceptor have been newly synthesized through the one-pot coupling cyclization key step. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using this dye. A solar-to-electric conversion efficiency of 6.65% and 4.70% is achieved with 1 and 2, respectively.
• FORMYLATION OF DIETHYL 2-THIENYLMETHYLPHOSPHONATE FOR ONE-POT SYNTHESIS OF AMINOTHIENOSTILBENECARBOXALDEHYDE
  作者：Cheng Zhang、Aaron W. Harper、Larry R. Dalton

  DOI：10.1081/scc-100104045

  日期：2001.1

  Diethyl 5-formyl-2-thienylmethylphosphonate is synthesized via the formylation of 2-thienylmethylphosphonate, and has been demonstrated to be an efficient intermediate thienylvinylene elongation of electron-rich conjugate systems.