2-Formylmethylene-5,6-dihydro-1,3-dithiolo<4,5-b><1,4>dithiin | 127661-07-8

• 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-Formylmethylene-5,6-dihydro-1,3-dithiolo<4,5-b><1,4>dithiin
• 英文别名: 4,5-ethylenedisulfanyl[1,3]ditiol-2-ylideneacetaldehyde；4,5-(ethylenedithio)-2-(formylmethylene)-1,3-dithiole；5,6-Dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylideneacetaldehyde；2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)acetaldehyde
• CAS: 127661-07-8
• 化学式: C₇H₆OS₄
• 分子量: 234.388
• InChiKey: CGMJFDJUEFLVIL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Formylmethylene-5,6-dihydro-1,3-dithiolo<4,5-b><1,4>dithiin 在 sodium tetrahydroborate 、 三乙胺 、 zinc(II) chloride 作用下， 以 乙腈 为溶剂， 生成 {2-[2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-ethylidene]-5-hydroxymethyl-[1,3]dithiol-4-yl}-methanol
  参考文献：
  名称：

  新型2-单和2,3-双（羟甲基）-6,7-乙撑二硫代TTF乙烯基胶的合成与性能

  摘要：

  描述了由于其醇官能度而易于产生氢键的标题化合物的合成。循环伏安法证明了这些衍生物是强大的π供体，能够用作相关有机金属的便捷前体。

  DOI：

  10.1016/0040-4039(95)00085-q
• 作为产物：
  描述：

  [2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-ethylidene]-diethyl-ammonium; iodide 以100%的产率得到2-Formylmethylene-5,6-dihydro-1,3-dithiolo<4,5-b><1,4>dithiin
  参考文献：
  名称：

  BEDT-TTF的乙烯基二乙叉基-2,2'-双（4,5-乙撑二硫-1,3-二硫醇）的合成与性能

  摘要：

  DOI：

  10.1007/bf00506862

文献信息

• Generation and Trapping of Phosphorus Stabilized 4,5-Ethylenedithio-1,3-dithiol-2-ide Carbanions: Synthesis of Ethylenedithio-1,3-dithiafulvalenes
  作者：Adrian J. Moore、Martin R. Bryce

  DOI：10.1055/s-1991-26370

  日期：——

  2-Dimethoxyphosphoryl-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]-2-dithiin (8) and 2-triphenylphosphonio-5,6-dihydro-1,3-dithiolo-[4,5-b][1,4]dithiin tetrafluoroborate (9) have been obtained in four steps from 4,5-ethylenedithio-1,3-dithiole-2-thione (4) (ca. 75% overall yield). Deprotonation of (8) and (9) yields the corresponding carbanion (10) and ylide (11) which have been trapped in good yield with glyoxal, cyclopentanone and anthraquinone to afford ethylenedithio-1,3-dithiafulvalenes.

  2-二甲氧基磷酸基-5,6-二氢-1,3-二噻烷-[4,5-b][1,4]-2-二硫烯 (8) 和 2-三苯基磷酸根-5,6-二氢-1,3-二噻烷-[4,5-b][1,4]二硫烯四氟硼酸盐 (9) 通过四个步骤从 4,5-乙烯二硫-1,3-二硫烯-2-硫酮 (4) 获得，整体产率约为 75%。对 (8) 和 (9) 去质子化得到相应的负离子 (10) 和亚磷烯 (11)，这两者与乙二醛、环戊酮和蒽醌反应，良好地捕获了产物，生成乙烯二硫-1,3-二硫丰烯。
• New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries
  作者：Shintaro Iwamoto、Yuu Inatomi、Daisuke Ogi、Satoshi Shibayama、Yukiko Murakami、Minami Kato、Kazuyuki Takahashi、Kazuyoshi Tanaka、Nobuhiko Hojo、Yohji Misaki

  DOI：10.3762/bjoc.11.128

  日期：——

  Derivatives of tris-fused TTF extended with two ethanediylidenes (5), tris- and pentakis-fused TTFs extended with two thiophene-2,5-diylidenes (6–9) were successfully synthesized. Cyclic voltammograms of the tetrakis(n-hexylthio) derivative of 5 and 7 (5d, 7d) consisted of two pairs of two-electron redox waves and two pairs of one-electron redox waves. On the other hand, four pairs of two-electron redox waves and two pairs of one-electron redox waves were observed for the tetrakis(n-hexylthio) derivative of 9 (9d). Coin-type cells using the bis(ethylenedithio) derivatives of 5 (5b), 6 (6b) and the tetrakis(methylthio) derivatives of 5 (5c) and 8 (8c) as positive electrode materials showed initial discharge capacities of 157–190 mAh g⁻¹ and initial energy densities of 535–680 mAh g⁻¹. The discharge capacities after 40 cycles were 64–86% of the initial discharge capacities.

  三联噻吩并三噻吩并二乙烯基扩展衍生物 (5)、三联噻吩并五噻吩并二噻吩-2,5-二基扩展衍生物 (6-9) 成功合成。四乙硫代己烷基衍生物的 5 和 7 (5d，7d) 的循环伏安图包含两对双电子氧化还原波和两对单电子氧化还原波。另一方面，四对双电子氧化还原波和两对单电子氧化还原波被观察到在四乙硫代己烷基衍生物的 9 (9d) 中。使用 5 (5b) 和 6 (6b) 的二乙烯基硫代衍生物以及 5 (5c) 和 8 (8c) 的四甲硫代衍生物作为正极材料的硬币型电池显示出初始放电容量为157-190mAh/g和初始能量密度为535-680mAh/g。40个循环后的放电容量为初始放电容量的64-86%。
• Exceptional electron donating ability of an extended tetrathiafulvalene derivative
  作者：Tahir Khan、Peter J. Skabara、Pierre Frère、Magali Allain、Simon J. Coles、Michael B. Hursthouse

  DOI：10.1016/j.tetlet.2004.02.003

  日期：2004.3

  We report the synthesis, crystal structures and redox chemistry of two new TTF derivatives bearing fused triaryl units. Both compounds show significant planarisation within conjugated regions, assisted by close intramolecular S⋯O contacts. The extended-TTF analogue displays multi-redox activity and can be oxidised sequentially to the tetracation species.

  我们报告了两个新的带有稠合三芳基单元的TTF衍生物的合成，晶体结构和氧化还原化学。在紧密的分子内S⋯O接触的辅助下，这两种化合物在共轭区内均表现出显着的平面化。扩展的TTF类似物显示出多种氧化还原活性，可以被顺序氧化成四阳离子种类。
• New bis(ethylenedithio)tetrathiafulvalene derivatives with low oxidation potentials
  作者：Adrian J. Moore、Martin R. Bryce、David J. Ando、Michael B. Hursthouse

  DOI：10.1039/c39910000320

  日期：——

  The efficient synthesis of three new vinylogous derivatives 6–8 of bis(ethylenedithio)tetrathiafulvalene (BEDT–TTF) is described; cyclic voltammetry establishes that the new donors have significantly lower solution oxidation potentials than that of BEDT–TTF, and the single crystal X-ray structure of compound 8 is described.

  描述了三种新的乙烯基衍生物6-8（双（乙撑二硫）四硫富瓦烯（BEDT-TTF））的高效合成；循环伏安法表明，新供体的溶液氧化电位明显低于BEDT-TTF，并描述了化合物8的单晶X射线结构。
• Novel D-π-A Chromophores Based on the Fulvene Accepting Moiety
  作者：Emad Aqad、Philippe Leriche、Gilles Mabon、Alain Gorgues、Vladimir Khodorkovsky

  DOI：10.1021/ol016143n

  日期：2001.7.1

  [GRAPHICS]Novel D-pi -A chromophores based on the fulvene accepting moiety and p-dimethylamino phenyl and 1,3-dithiole-2-ylidene donor moieties have been prepared. The X-ray structures of two representative derivatives have been determined. Examination of the UV-visible spectra and cyclic voltamperometry data revealed remarkable sensitivity of the electronic structure of these derivatives to substituents at the cyclopentadiene ring.