diethyl ester (2,5-diiodo-3-thienylmethyl)phosphonic acid | 883556-16-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl ester (2,5-diiodo-3-thienylmethyl)phosphonic acid
• 英文别名: diethyl diiodothiophenphosphonate；3-(Diethoxyphosphorylmethyl)-2,5-diiodothiophene
• CAS: 883556-16-9
• 化学式: C₉H₁₃I₂O₃PS
• 分子量: 486.049
• InChiKey: JGTQYPXJIRYLIO-UHFFFAOYSA-N

物化性质

• 沸点：
  454.6±45.0 °C(Predicted)
• 密度：
  2.006±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl ester (2,5-diiodo-3-thienylmethyl)phosphonic acid 在 四(三苯基膦)钯 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 (E)-1-((2',2'':5'',2'''-terthiophen)-3''-yl)-2-(2''''-pyridyl)ethene
  参考文献：
  名称：

  A modular procedure for the synthesis of functionalised β-substituted terthiophene monomers for conducting polymer applications

  摘要：

  An efficient modular strategy has been developed for the synthesis of beta-functionalised terthiophene monomers using Suzuki-Miyaura and Wittig/Horner-Emmons chemistries. This paper discusses the problems encountered with converting the beta-terthiophene aldehyde building block to the beta-terthiophene phosphonium salt and the use of this material in a Wittig condensation. An improved strategy using the beta-terthiophene phosphonate building block constructed via Suzuki-Miyaura coupling protocols was developed. We have synthesised and characterised a broad range of functionalised terthiophene materials that have been designed for specific end-use applications. The availability of these building blocks has dramatically increased access to a range of key monomers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.022
• 作为产物：
  描述：

  diethyl 3-thenylphosphonate 在 碘化吡啶单盐酸盐 、 mercury(II) nitrate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以86%的产率得到diethyl ester (2,5-diiodo-3-thienylmethyl)phosphonic acid
  参考文献：
  名称：

  A modular procedure for the synthesis of functionalised β-substituted terthiophene monomers for conducting polymer applications

  摘要：

  An efficient modular strategy has been developed for the synthesis of beta-functionalised terthiophene monomers using Suzuki-Miyaura and Wittig/Horner-Emmons chemistries. This paper discusses the problems encountered with converting the beta-terthiophene aldehyde building block to the beta-terthiophene phosphonium salt and the use of this material in a Wittig condensation. An improved strategy using the beta-terthiophene phosphonate building block constructed via Suzuki-Miyaura coupling protocols was developed. We have synthesised and characterised a broad range of functionalised terthiophene materials that have been designed for specific end-use applications. The availability of these building blocks has dramatically increased access to a range of key monomers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.022

文献信息

• Synthesis and characterization of novel styryl-substituted oligothienylenevinylenes
  作者：Pawel Wagner、Amy M. Ballantyne、Kenneth W. Jolley、David L. Officer

  DOI：10.1016/j.tet.2005.12.017

  日期：2006.3

  A number of 3-monosubstituted bis(thienylvinyl)thiophenes, suitable for the preparation of electronically-variable poly(thienytenevinylene)s have been synthesized for the first time. These materials have been characterized by both NMR spectroscopy and mass spectrometry, and a single crystal X-ray structure analysis of (E,E)-3-(5,5-dimethyl[1,3]dioxin-2-yl)-2,5-bis(2-thien-2-ylvinyl)thiophene has shown that the planarity of the terthienylenevinylene chain is maintained on substitution at the 3 position of the central thiophene ring. UV/visible spectroscopy measurements are reported and cyclic voltammetric measurements show that, with the exception of (E,E,E)-2,5-bis(2-thien-2-ylvinyl)-3-(2-(4-dimethylaminophenyl)vinyl)-thiophene, electroactive films are produced on electrochemical oxidation of the monomers. (c) 2005 Elsevier Ltd. All rights reserved.