4,5-ethylenediseleno-1,3-dithiol-2-one | 118355-61-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4,5-ethylenediseleno-1,3-dithiol-2-one
• 英文别名: 4,5-ethylenediseleno-1,3-dithiole-2-one；5,6-Dihydro-[1,4]diselenino[2,3-d][1,3]dithiol-2-one
• CAS: 118355-61-6
• 化学式: C₅H₄OS₂Se₂
• 分子量: 302.138
• InChiKey: SZYAEBQEPFGGAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-ethylenediseleno-1,3-dithiol-2-one 、 在 亚磷酸三乙酯 作用下， 反应 0.5h， 以34%的产率得到2-Azuleno[5,6-d][1,3]dithiol-2-ylidene-5,6-dihydro-[1,4]diselenino[2,3-d][1,3]dithiole
  参考文献：
  名称：

  Azulene-substituted TTF derivatives

  摘要：

  为了研究Little的有机超导体模型，我们合成了几种取代了苊的TTF衍生物。通过循环伏安法（CV）测量氧化电位，从而确定它们的供体能力。通过X射线分析确定了AET（苊基乙撑二硫代四硫富瓦烯）的分子结构。通过恒电流电解法，我们制备了合成供体的阳离子自由基盐，其中BF4–、ClO4–、PF6–、AsF6–和[Pt(dmit)2]n–（dmit=C3S52–=2-硫酮-1,3-二硫杂环戊烯-4,5-二硫醇酸根）的阳离子自由基盐。温度相关的电阻表明这些盐都是半导体的。通过X射线分析确定了（AET）2[Pt（dmit）2]的晶体结构，并讨论了其电子结构。

  DOI：

  10.1039/a703737f
• 作为产物：
  描述：

  5,6-dihydro-[1,4]diselenino[2,3-d][1,3]dithiole-2-thione 在 mercury(II) diacetate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4,5-ethylenediseleno-1,3-dithiol-2-one
  参考文献：
  名称：

  Papavassiliou, G. C.; Kakoussis, V. C.; Lagouvardos, D. J., Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 181, p. 171 - 184

  摘要：

  DOI：

文献信息

• Ethylenedithio(ethylenedioxo)diselenadithiafulvalene (TOST) and ethylenediseleno(ethylenedioxo)tetrathiafulvalene (SO): new unsymmetrical π-donors containing three elements in Group 16 (O, S, and Se)
  作者：Tatsuro Imakubo、Yoshinori Okano、Hiroshi Sawa、Reizo Kato

  DOI：10.1039/c39950002493

  日期：——

  The synthesis and characterization of new unsymmetrical bis(ethylenedithio)tetrathiafulvalene (ET) analogues ethylenedithio(ethylenedioxo)diselenadithiafulvalene (TOST) and ethyl enediseleno(ethylenedioxo)tetrathiafulvalene (SO) that contain three elements in group 16(O, S and Se) and their cation radical salts are reported.

  新型不对称双（亚乙基二硫代）四硫富瓦烯（ET）类似物的合成和表征，亚乙基二硫（亚乙基二氧代）二亚硒二硫富瓦烯（TOST）和乙基烯二烯丙基（亚乙基二氧代）四硫富富瓦烯（SO），它们在第16组（O，S和Se）中包含三个元素报道了阳离子自由基盐。
• Papavassiliou, G. C.; Kakoussis, V. C.; Lagouvardos, D. J., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1991, vol. 46, # 9, p. 1269 - 1271
  作者：Papavassiliou, G. C.、Kakoussis, V. C.、Lagouvardos, D. J.

  DOI：——

  日期：——
• 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.
• Abramov; Petrov, Russian Journal of General Chemistry, 1996, vol. 66, # 10, p. 1635 - 1640
  作者：Abramov、Petrov

  DOI：——

  日期：——
• NIGREY, P. J.;MOROSIN, B.;DUESLER, E., SYNTH. MET., 27,(1988) N-4, C. B481-B486
  作者：NIGREY, P. J.、MOROSIN, B.、DUESLER, E.

  DOI：——

  日期：——