2-(ethoxycarbonyl)tetrathiafulvalene | 63822-39-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 2-(ethoxycarbonyl)tetrathiafulvalene
• 英文别名: ethyl tetrathiafulvalenecarboxylate；Tetrathiofulvalen-monocarbonsaeureethylester；[2,2']bi[1,3]dithiolylidenecarboxylic acid ethyl ester；Ethyl 2-(1,3-dithiol-2-ylidene)-1,3-dithiole-4-carboxylate
• CAS: 63822-39-9
• 化学式: C₉H₈O₂S₄
• 分子量: 276.425
• InChiKey: NQZXOBSDYGCZOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  318.1±42.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(ethoxycarbonyl)tetrathiafulvalene 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 [2,2']Bi[[1,3]dithiolylidene]-4-carboxylic acid [2-(3,4,5-tris-dodecyloxy-benzoylamino)-ethyl]-amide
  参考文献：
  名称：

  Creation of a Mixed-Valence State from One-Dimensionally Aligned TTF Utilizing the Self-Assembling Nature of a Low Molecular-Weight Gel

  摘要：

  One-dimensional TTF assemblies have been obtained through the design of low molecular-weight gels, which show a characteristic absorption band at around 1750 nm upon I2 doping, assignable to a mixed-valence state of the TTF assemblies.

  DOI：

  10.1021/ja0552038
• 作为产物：
  描述：

  tetrathiafulvalene-4-carboxylic acid 在 吡啶 、 4-二甲氨基吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-(ethoxycarbonyl)tetrathiafulvalene
  参考文献：
  名称：

  Fluorocarbonyltetrathiafulvalene: an effective building block for the production of tetrathiafulvalene esters and amides

  摘要：

  4-Fluorocarbonyltetrathiafulvalene has been synthesised under mild conditions, and has been reacted with alcohols and amides to furnish esters and amides in near quantitative yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01804-3

文献信息

• Selective Functionalization of Tetrathiafulvalene Using Mg- and Zn-TMP-Bases: Preparation of Mono-, Di-, Tri-, and Tetrasubstituted Derivatives
  作者：Julia Nafe、Florian Auras、Konstantin Karaghiosoff、Thomas Bein、Paul Knochel

  DOI：10.1021/acs.orglett.5b02715

  日期：2015.11.6

  magnesium or zinc derivatives that are obtained by a direct metalation with Mg- and Zn-TMP-bases (TMP = 2,2,6,6-tetramethylpiperidyl). This stepwise functionalization provides access to a range of new mono-, di-, tri-, and tetra-functionalized TTF-derivatives and allows for fine-tuning of their energy levels.

  四硫富瓦烯骨架（TTF）通过镁或锌衍生物（通过与Mg和Zn-TMP碱直接金属化获得的镁或锌衍生物）在烯丙基化，酰化，芳基化，卤化和硫醇化反应中选择性反应（TMP = 2,2,6 ，6-四甲基哌啶基）。这种逐步的官能化作用提供了对一系列新的单，二，三和四官能化的TTF衍生物的访问，并允许对其能级进行微调。
• Three-dimensional supramolecular polymers driven by rigid tetrahedral building blocks through tetrathiafulvalene radical cation dimerization
  作者：Lan Chen、Shao-Chen Zhang、Hui Wang、Ya-Ming Zhou、Zhan-Ting Li、Dan-Wei Zhang

  DOI：10.1016/j.tet.2014.05.035

  日期：2014.8

  tetrahedral compounds T1 and T2 that bear four tetrathiafulvalene (TTF) units, which are connected to a tetraphenylmethane core by the ethynylene or amide linker were designed and prepared. Upon one-electron oxidation of the TTF units by Fe(ClO4)3, the resulting TTF+ radical cations stacked intermolecularly to give rise to three-dimensional supramolecular polymers, which were supported by UV–vis spectroscopy

  设计并制备了带有四个四硫富瓦烯（TTF）单元的刚性四面体化合物T1和T2，它们通过亚乙炔基或酰胺连接基连接到四苯基甲烷核上。通过Fe（ClO 4）3对TTF单元进行单电子氧化后，所得的TTF +自由基阳离子分子间堆叠，形成了三维超分子聚合物，并通过紫外可见光谱，循环伏安法，动态光散射进行了支持。 ，和扫描电子显微镜。
• Synthesis of amphiphilic, mono-functionalised tetrathiafulvalenes; X-ray crystal structure of 4-(6-sromohexanoyl)tetrathiafulvalene
  作者：Martin R. Bryce、Graeme Cooke、Ajaib S. Dhindsa、Dominique Lorcy、Adrian J. Moore、Michael C. Petty、Michael B. Hursthouse、A. I. Karaulov

  DOI：10.1039/c39900000816

  日期：——

  Reaction of monolithiated-tetrathiafulvalene (TTF) has been used in the synthesis of amphiphilic TTF derivatives bearing long chains attached through carbon, silicon, sulphur, selenium, and tellurium atoms; the single crystal X-ray structure of the title compound is described.

  单片化四硫富瓦烯（TTF）的反应已用于合成带有通过碳，硅，硫，硒和碲原子连接的长链的两亲性TTF衍生物。描述了标题化合物的单晶X射线结构。
• Unusually direct synthesis of mono- and di-substituted tetrathiafulvalenes
  作者：R.Alan Aitken、Lawrence Hill、Neil J Wilson

  DOI：10.1016/s0040-4039(99)80112-9

  日期：1999.1

  Direct reaction of norbornadiene, tributylphosphine, carbon disulfide and acetylenic diesters affords the norbornene-fused dihydrotetrathiafulvalenes 7 in addition to the bis-adducts 4 and for less reactive acetylenic dipolarophiles only 7 is isolated. Upon flash vacuum pyrolysis the compounds 7 undergo a retro Diels-Alder reaction to give substituted tetrathiafulvalenes 8. By using the norbornadiene

  除双加合物4外，降冰片二烯，三丁基膦，二硫化碳和炔属二酯的直接反应提供了降冰片烯稠合的二氢四硫富富瓦烯7，并且对于反应性较低的炔属双极性亲和剂仅分离出7。在快速真空热解后，化合物7进行逆狄尔斯-阿尔德反应，得到取代的四硫富瓦烯8。通过使用降冰片二烯二酯代替降冰片二烯和DMAD，可以更高的总产率获得8a。尝试分离两性离子结构9给出了具有新颖的1,2,5-三噻吩稳定的内酯结构11的重排产物。。
• GREEN D. C., J. ORG. CHEM., 1979, 44, NO 9, 1476-1479
  作者：GREEN D. C.

  DOI：——

  日期：——