4,5-Bis(benzoylseleno)-1,3-dithiole-2-thione | 119490-45-8

• 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: 4,5-Bis(benzoylseleno)-1,3-dithiole-2-thione
• 英文别名: 4,5-bis(benzoylseleno)-1,3-dithiol-2-thion；4,5-dibenzoyl seleno-1,3-dithiole-2-thion；4,5-Dibenzoylseleno-1,3-dithiol-2-thion；Se-(5-benzoylselanyl-2-sulfanylidene-1,3-dithiol-4-yl) benzenecarboselenoate
• CAS: 119490-45-8
• 化学式: C₁₇H₁₀O₂S₃Se₂
• 分子量: 500.383
• InChiKey: CMNLTQCZIACRAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-Bis(benzoylseleno)-1,3-dithiole-2-thione 在 cesium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 cesium 2-thioxo-1,3-dithiole-4,5-diselenolate
  参考文献：
  名称：

  Synthesis of novel tetrathiafulvalene derivatives with thiacrowns

  摘要：

  2-Thioxo-1,3-dithiole-4,5-diselenolate (DSIT) 二铯与双烷基化聚硫醚在高稀释度下缩合，可生成硫代噻吩化合物 4-7。经亚磷酸三乙酯处理后，化合物 5-7 转化为四硫杂戊烯衍生物 8-10。本文讨论了 6 的晶体结构以及四噻富戊烯 9 和 10 的循环伏安图。

  DOI：

  10.1039/p19960001995
• 作为产物：
  描述：

  (nBu4N)2[Zn(dsit)2] 、 苯甲酰氯 以 丙酮 为溶剂， 生成 4,5-Bis(benzoylseleno)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Preparation and Characterization of 5,6-Dimethyl-5,6-dihydro-[1,4]diselenino[ 2,3-d][1,3]dithiole-2-thione and Similar Compounds

  摘要：

  化合物5,6-二甲基-5,6-二氢-[1,4]二硒代[2,3-d][1,3]二硫代-2-硫酮，5-甲基-5,6-二氢-[1,4]二硒代[2,3-d][1,3]二硫代-2-硫酮和5,6-二氢-[1,4]二硒代[2,3-d]二硫代-2-硫酮已经制备并进行了分析和光谱表征。

  DOI：

  10.1515/znb-2003-0816

文献信息

• 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。
• Some New Nickel 1,2-Dichalcogenolene Complexes as Single-component Semiconductors
  作者：George C. Papavassiliou、George C. Anyfantis、Barry R. Steele、Barry R. Steele、Aris Terzis、Catherine P. Raptopoulou、George Tatakis、George Chaidogiannos、Nikos Glezos、Yufeng Weng、Harukazu Yoshino、Keizo Murata

  DOI：10.1515/znb-2007-0509

  日期：2007.5.1

  The complexes Ni(dmeds)(dmit), Ni(dmedt)(dmit), Ni(dpedt)(dsit), Ni(dpedt)(dmit), and Ni(dcdt)(dmit) (where dmeds is dimethylethylenediselenolate, dmedt is dimethylethylenedithiolate, dpedt is diphenylethylenedithiolate, dcdt is 1,2-bis-decylsulfanyl-ethene-1,2-dithiolate, dmit is 1,3-dithiol-2-thione-4,5-dithiolate, and dsit is 1,3-dithiol-2-thione-4,5-diselenolate) were prepared and characterized. The new complexes exhibit semiconducting behavior, with band gap values around 0.8 eV.

  标题：摘要 这些配合物 Ni(dmeds)(dmit)、Ni(dmedt)(dmit)、Ni(dpedt)(dsit)、Ni(dpedt)(dmit) 和 Ni(dcdt)(dmit)（其中 dmeds 是二甲基乙二硒酸酯，dmedt 是二甲基乙二硫酸酯，dpedt 是二苯基乙二硫酸酯，dcdt 是1,2-双癸硫醚-1,2-二硫酸酯，dmit 是1,3-二硫醚-2-硫酮-4,5-二硫酸酯，dsit 是1,3-二硫醚-2-硫酮-4,5-二硒酸酯）已被制备并表征。这些新的配合物表现出半导体行为，带隙值约为0.8电子伏特。
• Neue selenreiche 1,3-Dichalkogenol-2-selone via 4,5-Dilithio-1,3-dichalkogenol-2-selone
  作者：Helmut Poleschner、Reiner Radeglia、Joachim Fuchs

  DOI：10.1016/0022-328x(92)83086-w

  日期：1992.4

  1,3-Dithiole-2-thione (1), 1,3-diselenole-2-selone (2), 1,3-thiaselenole-2-thione (3), 1,3-dithiole-2-selone (4), 1,3-diselenole-2-thione (5) and 1,3-thiaselenole-2-selone (6) are dilithiated with lithium diisopropyl amide in the 4/5 position, followed by selenation (thiolation) and complexation of the resulting heterocyclic diselenolates (dithiolates) to the zinc bis-chelates (tetrabutylammonium or tetraphenylphosphonium salts).These zinc complexes react with benzoyl chloride to the corresponding selenole and thiole esters. It is noteworthy that the heterocyclic thiones with one or two ring selenium atoms undergo ring transformation (Dimroth rearrangement) during the lithiation chalcogenation sequence, whilst the thione sulfur and one ring selenium atom change their places: 3 --> 1,3-dithiole-2-selone-4,5-diselenolate or dithiolate structure, 5 --> 1,3-thiaselenole-2-selone-4,5-diselenolate structure. This observed rearrangement is verified by independent synthetic pathways. The corresponding identical zinc chelates 12 and complex 18 result from the precursors 3 and 4, and 5 and 6, respectively. Trapping experiments support the conclusion that this rearrangement takes place already during lithiation. The zinc chelates and thiole and selenole esters are characterized in detail by IR and above all by C-13 and Se-77 NMR spectroscopy, including NMR shift values of the precursor heterocycles. The X-ray crystal structure determination of bis(tetraphenylphosphonium)-bis(1,3-thiaselenole-2-selone-4,5-diselenolato) zincate (18), obtained from 5, shows the rearrangement of 5 to the 1,3-thiaselenole-2-selone partial structure in 18.
• Olk, Ruth-Maria; Roehr, Andreas; Olk, Bernhard, Zeitschrift fur Chemie, 1988, vol. 28, # 8, p. 304 - 305
  作者：Olk, Ruth-Maria、Roehr, Andreas、Olk, Bernhard、Hoyer, Eberhard

  DOI：——

  日期：——
• Synthesis and characterisation of [tris(1,3-dithiole-2-thione-4,5-dithiolato)-stannate]2−, [Q]2[Sn(dmit)3], [tris(1,3-dithiole-2-one-4,5-dithiolato)stannate]2−, [Q]2[Sn(dmio)3] and [tris(1,3-dithiole-2-thione-4,5-selenolato)stannate]2−, [Q]2[Sn(dsit)3], complexes
  作者：Fialho de Assis、Zahid H Chohan、R.Alan Howie、Abdullah Khan、John N Low、Gavin M Spencer、James L Wardell、Solange M.S.V Wardell

  DOI：10.1016/s0277-5387(99)00284-3

  日期：1999.11

  [Tris(1,3-dithiole-2-thione-4,5-dithiolato)stannate](2-), [Q](2)[Sn(C3S5)(3)], [tris(1,3-dithiole-2-one-4,5-dithiolato)stannate](2-), [Q](2)[Sn(C3S4O)(3)], and [tris(1,3-dithiole-2-thione-4,5-diselenolato)stannate](2-) [Q](2)[Sn(C3S3Se2)(3)], complexes, have been synthesised and characterised. Crystal structure determinations of [Q](2)[Sn(C3S5)(3)] (Q = 1,4-dimethylpyridinium, monoclinic and orthorhombic forms; NMe4, NEt4, and PPh4) and [NEt4](2)[Sn(C3S4O)(3)] revealed variations in the overall dianion structures. The geometry about tin in each case is essentially octahedral with the chelate bite angles in the range 80.7(5)-87.45(4)degrees: the range of Sn-S distances is 2.5207(18)-2.571(17) Angstrom. A statistical analysis, carried out on the crystal structure data for the six complexes, indicated that the most critical factors in controlling the overall shape of the dianion were the distances of the Sn atom from the dithiolate ligand planes [Sn-OOP]. Interanionic S ... S interactions, within the sum of the van der Waals' radii for two S atoms, are affected by the size of the cation, Q; the secondary connectivity is 3-dimensional for the smallest cations, Q = 1,4-dimethylpyridinium and NMe4, in chains for the somewhat larger cation, NEt4 and is absent for the still larger, PPh4 cation. (C) 1999 Elsevier Science Ltd. All rights reserved.