diethyl 3-thenylphosphonate | 21382-79-6

• 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 3-thenylphosphonate
• 英文别名: Diethyl [(thiophen-3-yl)methyl]phosphonate；3-(diethoxyphosphorylmethyl)thiophene
• CAS: 21382-79-6
• 化学式: C₉H₁₅O₃PS
• 分子量: 234.256
• InChiKey: COEUIMNMEJZFLM-UHFFFAOYSA-N

物化性质

• 沸点：
  137-140 °C(Press: 3 Torr)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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 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
• 作为产物：
  描述：

  3-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 9.0h， 生成 diethyl 3-thenylphosphonate
  参考文献：
  名称：

  3-取代的噻吩与芳基硼酸的区域选择性氧化偶联反应

  摘要：

  在优化的条件下，3-取代的噻吩（EWG = COOEt，PO（OEt）2）在碳原子C4处进行便捷的区域选择性氧化偶联反应。反应是在氧化银（2.0当量），三氟乙酸铯（tfa）（1.0当量），苯醌（BQ）（0.5当量）和催化量的Pd（tfa）2存在下，以各种芳基硼酸作为亲核试剂进行的。使用三氟乙酸（TFA）作为溶剂的（10mol％）。

  DOI：

  10.1021/ol201292v

文献信息

• Synthesis of fused heterocyclic systems via the Mallory photoreaction of arylthienylethenes
  作者：Natalia V. Dyachenko、Andrey V. Khoroshutin、Yulia A. Sotnikova、Valentina A. Karnoukhova、Sergey D. Tokarev、Alexander V. Anisimov、Yurii V. Fedorov、Olga A. Fedorova

  DOI：10.1039/c9pp00289h

  日期：2019.12

  Photochemical oxidative cyclization of 2- and 3-thienylstilbenes (heterostilbenes) containing mono-, di- and trimethoxy groups in the benzene ring or heterocyclic fragment results in the formation of isomeric thieno-annelated polycyclic aromatic compounds demonstrating optical properties that differ from those of initial stilbene derivatives. The structures of cyclic products were evaluated via1H and

  苯环或杂环片段中含有单，二和三甲氧基的2-和3-噻吩基苯乙烯（杂苯）的光化学氧化环化导致形成异噻吩基退火的多环芳族化合物，这表明其光学性质不同于最初的光学性质二苯乙烯衍生物。通过1 H和13 C NMR，HRMS，元素分析和X射线晶体学对环状产物的结构进行了评估。该研究旨在研究噻吩的二苯乙烯衍生物中的取代基以及噻吩核中苯乙烯基片段的位置对光环化反应发生的影响。
• Synthesis of phenanthro[<i>b</i>]thiophenes
  作者：Masatomo Iwao、Milton L. Lee、Raymond N. Castle

  DOI：10.1002/jhet.5570170623

  日期：1980.9

  All isomers of the parent phenanthro[b]thiophenes, namely, phenanthro[1,2-b]thiophene, phenanthro-[2,1-b]thiophene, phenanthro[2,3-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[3,4-b]thiophene, phenanthro[4,3-b]thiophene and phenanthro[9,10-b]thiophene have been synthesized.

  母菲并[ b ]噻吩的所有异构体，即菲[1,2- b ]噻吩，菲-[2,1- b ]噻吩，菲[2,3- b ]噻吩，菲[3,4-]合成了b ]噻吩，菲[3,4- b ]噻吩，菲[4,3- b ]噻吩和菲[9,10- b ]噻吩。
• Novel crown-containing 3-styryl derivatives of oligothiophenes: synthesis, structure, and optical and electrochemical characteristics
  作者：E. V. Lukovskaya、A. A. Bobyleva、O. A. Fedorova、Yu. V. Fedorov、A. V. Anisimov、Y. Didane、H. Brisset、F. Fages

  DOI：10.1007/s11172-009-0203-3

  日期：2009.7

  polythiophene derivatives including two crown-containing styryl fragments was proposed. The optical properties of the obtained compounds are characterized by the presence of intense absorption and fluorescence bands. The oxidation to the thiophene derivatives involves the crown-containing styryl fragment and should be sensitive to the presence of the metal cation in the crown ether cavity.

  提出了一种合成包含两个含冠苯乙烯基片段的 3-取代聚噻吩衍生物的方法。所得化合物的光学性质以存在强吸收带和荧光带为特征。噻吩衍生物的氧化涉及含冠的苯乙烯基片段，并且应该对冠醚腔中金属阳离子的存在敏感。
• A novel polythiophene derivative as a sensitive colorimetric and fluorescent sensor for anionic surfactants in water
  作者：Lin Wang、Qilong Feng、Xiangyong Wang、Meishan Pei、Guangyou Zhang

  DOI：10.1039/c2nj40460e

  日期：——

  A novel cationic polythiophene derivative, poly[N,N,N-trimethyl-4-(thiophen-3-ylmethylene)cyclohexanaminium chloride] (PTCA-Cl), has been prepared successfully and applied as a colorimetric and fluorometric probe for the detection of anionic surfactants. In particular, a new method for the polymerization of cationic polythiophene derivatives is found, which has not been reported previously. The colorimetric

  一种新型的阳离子聚噻吩衍生物，聚[ N，N，N[三甲基-4-（噻吩-3-基亚甲基）环己氯化铵]（PTCA-Cl）已成功制备，并用作比色和荧光探针，用于检测阴离子表面活性剂。特别地，发现了聚合阳离子聚噻吩衍生物的新方法，该方法以前没有被报道过。通过吸收和发射光谱研究了PTCA-Cl对阴离子表面活性剂的比色和荧光响应。可以用肉眼明显地观察到传感相互作用，这为它的实际应用提供了很大的优势。此外，传感器（PTCA-Cl）在存在其他带负电荷的分析物的情况下，对阴离子表面活性剂具有很高的选择性，并且灵敏度很高，检测极限为10 -9使用荧光法测定M，这是目前所有可用的合成阴离子表面活性剂传感器中最低的。因此，水溶性聚噻吩衍生物可以用作比色和荧光探针，以高选择性和高灵敏度检测阴离子表面活性剂。
• Facile Synthesis of Thienoquinolines and Thienoisoquinolines via Photocyclization
  作者：A. L. Marzinzik、P. Rademacher

  DOI：10.1055/s-1995-4062

  日期：1995.9

  A synthetic route starting from diethyl thenylphosphonates offers a facile and efficient method for the preparation of new isomeric thienoquinolines and thienoisoquinolines. Their structure and heteronuclear connectivity information was unambiguously established by analysis of NMR data using CH COSY and HMBC techniques.

  以二乙基膦酸盐为起点的合成路线为制备新的异构噻吩喹啉和噻吩异喹啉提供了一种简便高效的方法。通过使用 CH COSY 和 HMBC 技术分析核磁共振数据，明确地确定了它们的结构和异核连接信息。