4-benzoylthio-5-methylthio-1,3-dithiole-2-thione | 161090-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzoylthio-5-methylthio-1,3-dithiole-2-thione
• 英文别名: 4-methylthio-5-benzoylthio-1,3-dithiole-2-thione；4-(benzoylthio)-5-(methylthio)-2-thioxo-1,3-dithiole；S-(5-methylsulfanyl-2-sulfanylidene-1,3-dithiol-4-yl) benzenecarbothioate
• CAS: 161090-91-1
• 化学式: C₁₁H₈OS₅
• 分子量: 316.514
• InChiKey: GJTZFQJFEKJZCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  4-benzoylthio-5-methylthio-1,3-dithiole-2-thione 在 cesium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.02h， 以54%的产率得到cesium 4-(methylthio)-2-thioxo-1,3-dithiole-5-thiolate
  参考文献：
  名称：

  铸币金属硫醚-硫醇配合物的合成及晶体结构

  摘要：

  铜 (I)、银 (I) 和两种 (Ph3P)nM(L) [n = 1, 2, 3; L = 4-(methylthio)-2-thioxo-1,3-dithiole-5-thiolate (La), 1,2-dicyano-1-(methylthio)ethene-2-thiolate (Lb)] 已经合成。这些配合物的分子结构由 X 射线晶体学确定，并显示出这些 (Ph3P)nM(L) 配合物的配位硫原子和配位几何结构的差异。在 (Ph3P)2Cu(L) (2) 中，硫醚硫醇盐配体作为双齿配体，而在银和金配合物 (Ph3P)3Ag(L) (3) 和 (Ph3P)2Au(L) (4) 中，只有硫醇硫被配位。(Ph3P)2Au(La) (4a) 的磷烷配体之一在沸腾的丙酮中发生解离，得到线性双配位金 (I) 中心 (Ph3P)Au(La) (5a)。

  DOI：

  10.1002/1099-0682(200106)2001:6<1535::aid-ejic1535>3.0.co;2-p
• 作为产物：
  描述：

  4,5-双(苯甲酰硫基)-1,3-二硫杂环戊烯-2-硫酮 在 cesium hydroxide 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 24.02h， 生成 4-benzoylthio-5-methylthio-1,3-dithiole-2-thione
  参考文献：
  名称：

  Synthesis and Reactions of Thioether-Thiolate Compounds of 1,3-Dithiole-2-thione-4,5-dithiolate (dmit)

  摘要：

  报告了一种制备不对称取代的 1,3-二硫代-2-硫酮-4,5-二硫酸盐（dmit）的有效方法。通过获得各种 1,3-二硫代-2-硫酮-4-硫醇酯-5-硫酯和醚，证明了该方法的应用。从这些化合物出发，展示了一条通往新型不对称冠化合物和四噻吩富戊烯的便捷路线。

  DOI：

  10.1055/s-1994-25711

文献信息

• Synthesis of Pyrazinoporphyrazine Derivatives Functionalised with Tetrathiafulvalene (TTF) Units: X-Ray Crystal Structures of Two Related ttf Cyclophanes and Two Bis(1,3-Dithiole-2-Thione) Intermediates
  作者：C. S. Wang、M. R. Bryce、A. S. Batsanov、J. A. K. Howard

  DOI：10.1002/chem.19970031018

  日期：1997.10

  AbstractThe pyrazinoporphyrazine system 13 (metal‐free, zinc and copper derivatives) has been synthesised by tetramerisation of 2,3‐dicyanopyrazine monomer unit 10. The structure of 13a‐c has been established by 1H NMR spectroscopy, UV/Vis spectrophotometry, MALDI‐TOF mass spectrometry, cyclic voltammetry and differential pulse voltammetry. The electrochemical redox behaviour of 13a‐c is strongly solvent dependent. The expected two‐stage oxidation of the tetrathiafulvalene (TTF) units of 13a‐c was observed in a range of solvents; in addition, oxidation and reduction of the pyrazinoporphyrazine core of the metal‐free derivative 13a was detected in benzonitrile. On excitation of 13 in the Q‐band region no fluorescence was observed, which is presumably the consequence of intramolecular charge transfer between the TTF moieties and the excited state of the central porphyrazine. Molecular modelling studies on 13a and 13c are reported. During the course of this work, the novel TTF macrocycles 11 and 20 were synthesised; their X‐ray crystal structures reveal severely bent TTF units, the conformations of which are discussed in detail. The X‐ray crystal structures of the bis(1,3‐dithiole) systems 15 and 18 have also been determined.
• Synthesis and Reactions of Thioether-Thiolate Compounds of 1,3-Dithiole-2-thione-4,5-dithiolate (dmit)
  作者：Stephan Zeltner、Ruth-Maria Olk、Michael Wagner、Bernhard Olk

  DOI：10.1055/s-1994-25711

  日期：——

  An efficient method for the preparation of the unsymmetrically substituted 1,3-dithiole-2-thione-4,5-dithiolate (dmit) is reported. Its application is demonstrated by obtainment of various 1,3-dithiole-2-thione-4-thiolate-5-thioesters and ethers. Starting from these compounds an expedient route to novel unsymmetrical crown compounds and tetrathiafulvalenes is shown.

  报告了一种制备不对称取代的 1,3-二硫代-2-硫酮-4,5-二硫酸盐（dmit）的有效方法。通过获得各种 1,3-二硫代-2-硫酮-4-硫醇酯-5-硫酯和醚，证明了该方法的应用。从这些化合物出发，展示了一条通往新型不对称冠化合物和四噻吩富戊烯的便捷路线。
• Syntheses and Crystal Structures of Coinage Metal Thioether-Thiolato Complexes
  作者：Stephan Zeltner、Svea Jelonek、Joachim Sieler、Ruth-Maria Olk

  DOI：10.1002/1099-0682(200106)2001:6<1535::aid-ejic1535>3.0.co;2-p

  日期：2001.6

  gold(I) complexes of the type (Ph3P)nM(L) [n = 1, 2, 3; L = 4-(methylthio)-2-thioxo-1,3-dithiole-5-thiolate (La), 1,2-dicyano-1-(methylthio)ethene-2-thiolate (Lb)] have been synthesized. The molecular structure of these complexes was determined by X-ray crystallography and shows differences in the coordinated sulfur atoms as well as in the coordination geometry of these (Ph3P)nM(L) complexes. In (Ph3P)2Cu(L)

  铜 (I)、银 (I) 和两种 (Ph3P)nM(L) [n = 1, 2, 3; L = 4-(methylthio)-2-thioxo-1,3-dithiole-5-thiolate (La), 1,2-dicyano-1-(methylthio)ethene-2-thiolate (Lb)] 已经合成。这些配合物的分子结构由 X 射线晶体学确定，并显示出这些 (Ph3P)nM(L) 配合物的配位硫原子和配位几何结构的差异。在 (Ph3P)2Cu(L) (2) 中，硫醚硫醇盐配体作为双齿配体，而在银和金配合物 (Ph3P)3Ag(L) (3) 和 (Ph3P)2Au(L) (4) 中，只有硫醇硫被配位。(Ph3P)2Au(La) (4a) 的磷烷配体之一在沸腾的丙酮中发生解离，得到线性双配位金 (I) 中心 (Ph3P)Au(La) (5a)。