1,3-Dithiole-2-selenone | 53555-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1,3-Dithiole-2-selenone
• 英文别名: 1,3-dithiole-2-selone；1,3-Dithiol-2-selon；[1,3]dithiole-2-selone
• CAS: 53555-44-5
• 化学式: C₃H₂S₂Se
• 分子量: 181.141
• InChiKey: TVRODKXXALRSQN-UHFFFAOYSA-N

物化性质

• 熔点：
  59 °C
• 沸点：
  271.2±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-Dithiole-2-selenone 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以92%的产率得到2-Methylselanyl-1,3-dithiol-1-ium;trifluoromethanesulfonate
  参考文献：
  名称：

  2-(Triphenylphosphonio)-4,5-bis(thiobenzoyl)-1,3-dithiole Tetrafluoroborate: A Versatile Wittig Reagent for the Synthesis of Unsymmetrical Tetrathiafulvalenes and 1,3-Dithiol-2-ylidene Derivatives

  摘要：

  The title Wittig reagent 5 has been prepared in three steps (84% overall yield) from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione. Reactions of ylide 7, generated by treatment of 5 with diisopropylethylamine at room temperature, have been exploited in the synthesis of new unsymmetrical tetrathiafulvalenes and 1,3-dithiol-2-ylidene derivatives. Subsequent removal of the benzoyl protecting group with sodium ethoxide liberates the transient TTF-dithiolate or 1,3-dithiole-dithiolate anions which can be alkylated in situ. The X-ray crystal structures of compounds 17 and 18 are reported: close nonbonded S-O intramolecular interactions are observed in both structures.

  DOI：

  10.1021/jo00097a038
• 作为产物：
  描述：

  1,3-Thiaselenole-2-thione 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 以200 mg的产率得到1,3-Dithiole-2-selenone
  参考文献：
  名称：

  Synthesis of sym-(E/Z)-diselenadithiafulvalene

  摘要：

  DOI：

  10.1021/jo01301a018

文献信息

• 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.
• Guziec, Frank S.; Russo, Joseph M.; Torres, Felix F., Journal of the Chemical Society. Perkin transactions I, 1989, p. 1068 - 1070
  作者：Guziec, Frank S.、Russo, Joseph M.、Torres, Felix F.、Long, G. Cornell、Tellez, Mario R.

  DOI：——

  日期：——
• Synthese und Eigenschaften von 1,4,3-Thiaselenazin, einem neuen heterocyclischen System
  作者：Helmut Poleschner、Jürgen Böttger、Egon Fanghänel

  DOI：10.1055/s-1984-30927

  日期：——
• Poleschner, H.; Radeglia, R.; Fanghaenel, E., Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 5, p. 737 - 746
  作者：Poleschner, H.、Radeglia, R.、Fanghaenel, E.

  DOI：——

  日期：——
• Fabre J. M., Chakroune S., Giral L., Gorgues A., Salle M., Synth. Metals., 56 (1993) N 1, S 2073-2077
  作者：Fabre J. M., Chakroune S., Giral L., Gorgues A., Salle M.

  DOI：——

  日期：——