diethyl ester (3'-methylene-2:2',5':2''-terthiophene)phosphonic acid | 393109-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: diethyl ester (3'-methylene-2:2',5':2''-terthiophene)phosphonic acid
• 英文别名: 3-(Diethoxyphosphorylmethyl)-2,5-dithiophen-2-ylthiophene
• CAS: 393109-72-3
• 化学式: C₁₇H₁₉O₃PS₃
• 分子量: 398.508
• InChiKey: LJZWFNMIMPITRR-UHFFFAOYSA-N

物化性质

• 沸点：
  515.4±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-formyl-2,2':5',2''-terthiophene 、 diethyl ester (3'-methylene-2:2',5':2''-terthiophene)phosphonic acid 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 以86%的产率得到(E)-1,2-bis((2',2'':5'',2'''-terthiophen)-3''-yl)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 四(三苯基膦)钯 碘化吡啶单盐酸盐 、 sodium carbonate 、 mercury(II) nitrate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 14.5h， 生成 diethyl ester (3'-methylene-2:2',5':2''-terthiophene)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

• β-Terthiophene aldehyde and phosphonate: key building blocks for the synthesis of functionalised conducting polymers
  作者：Gavin E Collis、Anthony K Burrell、David L Officer

  DOI：10.1016/s0040-4039(01)01894-9

  日期：2001.12

  A simple and efficient methodology has been developed for the synthesis of beta -functionalised terthiophene monomers, conducting polymer precursors. Using a building block approach, the key materials, beta -terthiophene aldehyde and phosphonate, were constructed with Suzuki chemistry. Reactions of these building blocks with the appropriate coupling partner under Wittig/Horner-Emmons conditions provides conjugatively-linked functionalised monomers. (C) 2001 Elsevier Science Ltd. All rights reserved.