2-thioxo-5H-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one | 129993-53-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-thioxo-5H-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one
• 英文别名: 5H-1,3-Dithiolo[4,5-b][1,4]dithiepin-6(7H)-one, 2-thioxo-；2-sulfanylidene-[1,3]dithiolo[4,5-b][1,4]dithiepin-6-one
• CAS: 129993-53-9
• 化学式: C₆H₄OS₅
• mdl: MFCD00807824
• 分子量: 252.427
• InChiKey: MFRWFNJNFMWPJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-thioxo-5H-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到6,6-difluoro-5,7-dihydro-5H-[1,3]-dithiolo[4,5-b][1,4]-dithiepin-2-thione
  参考文献：
  名称：

  基于F ... F非键相互作用的具有保留的电子给体性质和氟化的双层结构的氟化四硫富瓦烯

  摘要：

  用DAST合成氟化的4,5-（2,2'-二氟丙烯二硫基）-1,3-二硫醇-2-酮杂环可以制备几种对称和不对称的二氟和四氟取代的四硫富瓦烯，它们具有可及的氧化势尽管存在吸电子CF2基团（相对于SCE，0.6

  DOI：

  10.1021/jo000518l
• 作为产物：
  描述：

  bis(tetraetylammonium) bis(thioxo-1,3-dithiole-4,5-dithiolato)zincate(II) 、 1,3-二氯丙酮 以 乙腈 为溶剂， 反应 3.0h， 以76%的产率得到2-thioxo-5H-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one
  参考文献：
  名称：

  衍生自4,5-（丙烯二硫基）-1,3-二硫醇单元的功能化四硫富瓦烯（TTF）系统

  摘要：

  制备了一系列含有取代的4,5-（丙烯二硫基）-1,3-二硫醇单元的官能化对称和不对称四硫富瓦烯（TTF）衍生物。关键的半单元是叔丁基二苯基甲硅烷基保护的1,3-二硫醇衍生物18和缩酮保护的衍生物32。在亚磷酸三乙酯的存在下，这些半单元与1,3-二硫代-2-酮和-2-硫酮衍生物19-22的自偶联和交叉偶联反应发生。脱保护后，TTF衍生物14，24，28，34和40-43中，获得轴承羟基或酮官能团。14，24和28的一个或多个醇基团的官能化用酰氯和异氰酸酯已经获得了化合物16、17、25、26和29。循环伏安研究表明，新的TTF衍生物是有效的π电子供体。它们经历了两个可逆的单电子氧化还原波。4,5-（2-羟基丙烯二硫基）-1,3-二硫基-2-硫酮3和缩酮蛋白的X射线晶体结构

  DOI：

  10.1016/s0040-4020(01)80428-2

文献信息

• Synthesis of new multi-sulphur π-electron donors containing ketone functionality
  作者：Martin R. Bryce、Gary J. Marshallsay

  DOI：10.1016/s0040-4039(00)79457-3

  日期：1991.10

  Five new tetrathiafulvalene derivatives, (8) and (17)–(20), which contain ketone functionality incorporated into the heterocyclic framework have been synthesised; cyclic voltammetry establishes that they are efficient -electron donors which undergo two, reversible, one-electron redox waves.

  已经合成了五种新的四硫富瓦烯衍生物（8）和（17）-（20），它们都含有并入杂环骨架的酮官能团。循环伏安法证明它们是有效的电子给体，它经历了两个可逆的单电子氧化还原波。
• Synthetic strategies to chiral organosulfur donors related to bis(ethylenedithio)tetrathiafulvalene
  作者：Jon-Paul Griffiths、Hui Nie、R. James Brown、Peter Day、John D. Wallis

  DOI：10.1039/b502437d

  日期：——

  Syntheses of enantiopure organosulfur donors by three different strategies requiring only four–six steps are reported. The key step involves either double substitution of an enantiopure cyclic sulfate ester by a dithiolate, attachment of a chiral diol as a ketal, or completely diastereoselective cycloaddition of 1,3-dithiole-2,4,5-trithione to an enantiopure alkene.

  报告采用三种不同的策略合成了对映体纯有机硫给体，只需要四到六个步骤。关键步骤包括对映体纯环硫酸酯与二硫醇的双取代、手性二元醇作为酮体的连接，或 1,3-二硫代-2,4,5-三硫酮与对映体纯烯的完全非对映选择性环加成。
• A new self-assembled copper(I) complex of 2-thioxo-5H-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one showing three-dimensional supramolecular networks
  作者：Jing-Lin Zuo、Jun-Feng Bai、Zhen Shen、Xiao-Zeng You、Hoong-Kun Fun、Kandasamy Chinnakali、Chi-Ming Che

  DOI：10.1016/s0020-1693(99)00155-3

  日期：1999.9

  The synthesis and structural characterization of a supramolecular copper(I) complex of 2-thioxo-1,3-dithiolo[4,5-b][1,4]dithiepin-6(7H)-one are described. The complex crystallized in the orthorhombic space group Pna21 with the cell dimensions a=12.9124(2), b=20.7944(2), c=4.4457(1) Å, V=1193.70(3) Å3 and Z=4. The structure was refined to a final agreement factor R=0.0295. The C6H4OS5Cu units are connected

  描述了2-thioxo-1,3-dithiolo [4,5- b ] [1,4] dithiepin-6（7 H）-one的超分子铜（I）配合物的合成和结构表征。复合物中的斜方晶系，空间群结晶PNA 2 1与细胞尺寸一个= 12.9124（2），b = 20.7944（2），C ^ = 4.4457（1）埃，V = 1193.70（3）3和Ž = 4。将结构精炼为最终的协议因子R = 0.0295。C 6 H 4 OS 5Cu单元通过桥接碘原子而连接以形成梯形结构。Cu⋯Cu的间距为2.9884（9）Å，并且短的S⋯S和S⋯I接触链间形成了一个新颖的三维网络。
• Sulfur-rich CpCo(dithiolene) complexes: Isostructural or non-isostructural couples of CpCo(III) with CpNi(III) dithiolene complexes
  作者：Mitsushiro Nomura、Shigemi Kondo、Souichi Yamashita、Eriko Suzuki、Yoshiko Toyota、Glenn V. Alea、Gerardo C. Janairo、Chikako Fujita-Takayama、Toru Sugiyama、Masatsugu Kajitani

  DOI：10.1016/j.jorganchem.2010.05.024

  日期：2010.10

  Eight new sulfur-rich [CpCo(dithiolene)] complexes were synthesized from [Zn(dmit)(2)](2-) as a starting material. The structures, electrochemical behavior and electronic absorption spectra of the sulfur-rich [CpCo(S2C2S2Y)] complexes could be compared with the early data of analogous Ni complexes. [CpCo (pddt)] (Y= -(CH2)(3)-), [CpCo(dpdt)] (Y = -CH2C(CH2)CH2-), [CpCo(bddt)] (Y = -(CH2)(4)-), [CpCo(dtdt)] (Y = -CH2SCH2-) and [CpCo(poddt)] (Y = -CH2C(O)CH2-) crystallized in all isostructural with the corresponding paramagnetic [CpNi(dithiolene)](center dot) complexes, but [CpCo(dmid)] (Y =C=O), [CpCo(dddt)] (Y= -(CH2)(2)-) and [CpCo(F(2)pddt)] (Y= -CH2CF2CH2-) crystallized in non-isostructural with them. These molecules are associated with intermolecular short S center dot center dot center dot S contacts in the crystals. [CpCo(F(2)pddt)] did not show any remarkable S center dot center dot center dot S contacts but indicated interesting fluorine segregation and Cp center dot center dot center dot Cp face-to-face interactions. Redox potentials of [CpCo(dithiolene)] complexes were obtained with the cyclic voltammetry measurements and dimerized by electrochemical oxidations. Electronic absorption spectra of [CpCo(dithiolene)] complexes showed visible absorption in the range of 585-701 nm as lowest energy wavelengths (epsilon = 9800-11,800 M-1 cm(-1)) in solutions, and they were higher energy than those of [CpNi (dithiolene)](center dot) complexes (near-IR). (C) 2010 Elsevier B.V. All rights reserved.
• Russkikh; Abashev; Shklyaeva, Russian Journal of Organic Chemistry, 1997, vol. 33, # 3, p. 408 - 413
  作者：Russkikh、Abashev、Shklyaeva

  DOI：——

  日期：——