4-(2-Hydroxyethylthio)tetrathiafulvalene | 138682-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 4-(2-Hydroxyethylthio)tetrathiafulvalene
• 英文别名: 2-[[2-(1,3-Dithiol-2-ylidene)-1,3-dithiol-4-yl]sulfanyl]ethanol
• CAS: 138682-21-0
• 化学式: C₈H₈OS₅
• 分子量: 280.481
• InChiKey: GIJLBWBUCLFFIX-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2-Hydroxyethylthio)tetrathiafulvalene 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-malonic acid bis-[2-([2,2']bi[[1,3]dithiolylidene]-4-ylsulfanyl)-ethyl] ester
  参考文献：
  名称：

  Bis- and tris(tetrathiafulvalenes) (TTFs) derived from reactions of the TTF-thiolate anion

  摘要：

  A range of new bis- and tris-TTF derivatives has been prepared using the TTF-thiolate anion 2 as a key intermediate. Thiolate anion 2 reacts with 2-bromoethanol to yield alcohol 3 from which the bis- and tris-TTF systems 4-7 have been obtained by reaction with the appropriate acid chloride. Subsequent reactions of the malonate anion of dimeric TTF 7 yield derivatives 8-10, which include the amphiphilic system 8. Thiolate anion 2 reacts with bis- and tris(bromomethyl)benzene to yield bis- and tris-TTF derivatives 11 and 12, respectively. Thioester 13, which serves as a shelf-stable precursor of thiolate anion 2, has been used in the synthesis of bis-TTF systems 17 and 18. The solution electrochemistry of the new multi-TTF derivatives has been studied by cyclic voltammetry, which reveals that the TTF moieties do not interact to any significant extent.

  DOI：

  10.1021/jo00044a020
• 作为产物：
  描述：

  四硫富瓦烯 、 2-溴乙醇 生成 4-(2-Hydroxyethylthio)tetrathiafulvalene
  参考文献：
  名称：

  Bis- and tris(tetrathiafulvalenes) (TTFs) derived from reactions of the TTF-thiolate anion

  摘要：

  A range of new bis- and tris-TTF derivatives has been prepared using the TTF-thiolate anion 2 as a key intermediate. Thiolate anion 2 reacts with 2-bromoethanol to yield alcohol 3 from which the bis- and tris-TTF systems 4-7 have been obtained by reaction with the appropriate acid chloride. Subsequent reactions of the malonate anion of dimeric TTF 7 yield derivatives 8-10, which include the amphiphilic system 8. Thiolate anion 2 reacts with bis- and tris(bromomethyl)benzene to yield bis- and tris-TTF derivatives 11 and 12, respectively. Thioester 13, which serves as a shelf-stable precursor of thiolate anion 2, has been used in the synthesis of bis-TTF systems 17 and 18. The solution electrochemistry of the new multi-TTF derivatives has been studied by cyclic voltammetry, which reveals that the TTF moieties do not interact to any significant extent.

  DOI：

  10.1021/jo00044a020

文献信息

• Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF)
  作者：Adrian J. Moore、Martin R. Bryce、Graeme Cooke、Gary J. Marshallsay、Peter J. Skabara、Andrei S. Batsanov、Judith A. K. Howard、Stephen T. A. K. Daley

  DOI：10.1039/p19930001403

  日期：——

  particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. Onepot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular

  单硅化四硫富瓦烯（TTF）与元素硫或元素硒在–78°C的反应产生瞬态物质TTF-S – Li +和TTF-Se – Li +分别被一系列烷基卤捕获，得到了新的烷基硫代和烷基硒代TTF衍生物。TTF-硫醇盐阴离子与2-溴乙醇的反应生成4-（2-羟乙基硫基）四硫富瓦烯，它是用于合成一系列新的含醚，酯，丙烯酸酯，氨基甲酸酯和乙烯基硫基的新型单官能化TTF衍生物的通用型结构单元侧链中的基团。据报道，由TTF一锅合成乙二硫基-TTF（EDT-TTF）和乙二硒基-TTF（EDS-TTF）。EDS-TTF的结构已通过单晶X射线分析确定，该分析揭示了分子平面彼此正交的二聚体。
• Covalently attached ferrocene and tetrathiafulvalene redox systems
  作者：Adrian J. Moore、Peter J. Skabara、Martin R. Bryce、Andrei S. Batsanov、Judith A. K. Howard、Stephen T. A. K. Daley

  DOI：10.1039/c39930000417

  日期：——

  The synthesis and solution redox properties of several covalently attached ferrocene and tetrathiafulvalene units are reported, together with the X-ray crystal structure of a 1,1′-bis(1,3-dithiole-2-ylidene)-substituted ferrocene derivative.

  报道了几个共价连接的二茂铁和四硫富瓦烯单元的合成和溶液的氧化还原性质，以及1,1'-双（1,3-二硫代-2-亚烷基）取代的二茂铁衍生物的X射线晶体结构。
• Highly-functionalised tetrathiafulvalene (TTF) derivatives
  作者：Adrian J. Moore、Martin R. Bryce

  DOI：10.1039/c39910001638

  日期：——

  Efficient syntheses are described for a range of new functionalised tetrathiafulvalene donors, notably those substituted with vinylthio and acrylate groups; solution redox properties have been studied by cyclic voltammetry.

  描述了一系列新型官能化的四硫富瓦烯给体的有效合成方法，特别是被乙烯基硫基和丙烯酸酯基取代的那些。循环伏安法研究了溶液的氧化还原特性。
• Bis- and tris(tetrathiafulvalenes) (TTFs) derived from reactions of the TTF-thiolate anion
  作者：Martin R. Bryce、Gary J. Marshallsay、Adrian J. Moore

  DOI：10.1021/jo00044a020

  日期：1992.8

  A range of new bis- and tris-TTF derivatives has been prepared using the TTF-thiolate anion 2 as a key intermediate. Thiolate anion 2 reacts with 2-bromoethanol to yield alcohol 3 from which the bis- and tris-TTF systems 4-7 have been obtained by reaction with the appropriate acid chloride. Subsequent reactions of the malonate anion of dimeric TTF 7 yield derivatives 8-10, which include the amphiphilic system 8. Thiolate anion 2 reacts with bis- and tris(bromomethyl)benzene to yield bis- and tris-TTF derivatives 11 and 12, respectively. Thioester 13, which serves as a shelf-stable precursor of thiolate anion 2, has been used in the synthesis of bis-TTF systems 17 and 18. The solution electrochemistry of the new multi-TTF derivatives has been studied by cyclic voltammetry, which reveals that the TTF moieties do not interact to any significant extent.