4,5-Dibenzoylseleno-1,3-diselenol-2-selon | 94516-67-3

• 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-Dibenzoylseleno-1,3-diselenol-2-selon
• 英文别名: Se-(5-benzoylselanyl-2-selanylidene-1,3-diselenol-4-yl) benzenecarboselenoate
• CAS: 94516-67-3
• 化学式: C₁₇H₁₀O₂Se₅
• 分子量: 641.065
• InChiKey: XWQQFCXCCCKSDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-Dibenzoylseleno-1,3-diselenol-2-selon 在 cesium hydroxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.02h， 以90%的产率得到caesium 4-benzoylseleno-1,3-diselenole-2-selone-5-selenolate
  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
• 作为产物：
  描述：

  苯甲酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 以 丙酮 为溶剂， 反应 0.25h， 以70%的产率得到4,5-Dibenzoylseleno-1,3-diselenol-2-selon
  参考文献：
  名称：

  Neue selenreiche 1,3-Dichalkogenol-2-selone via 4,5-Dilithio-1,3-dichalkogenol-2-selone

  摘要：

  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.

  DOI：

  10.1016/0022-328x(92)83086-w

文献信息

• In(III), Tl(III) and V(IV) tris-chelates of the heterocyclic dithiolene and diselenolene ligands 1,3-dithiole-2-thione-4,5-dithiolate (dmit), 1,2-dithiole-3-thione-4,5-dithiolate (dmt) and 1,3-diselenole-2-selone-4,5-diselenolate (dsis). Crystal and molecular structure of (Bu4N)2 [V(dmt)3]
  作者：Ruth-Maria Olk、W. Dietzsch、R. Kirmse、J. Stach、E. Hoyer、L. Golič

  DOI：10.1016/s0020-1693(00)86553-6

  日期：1987.4

  Abstract Synthesis and characterization of the first trischelates of the dichalcogenolene ligands 1,3-dithiole-2-thione-4,5-dithiolate (dmit), 1,2-dithiole-3-thione-4,5-dithiolate (dmt)and 1,3-diselenole-2-selone-4,5-diselenolate (dsis) with the central ions In(III), Tl(III) and V(IV) are reported. On (Bu4N)2[V(dmt)3] the first X-ray structure of a dithiolene tris-chelate containing unsymmetric ligand

  摘要二氯萘酚配体1,3-二硫代-2-硫酮-4,5-二硫代（dmit），1,2-二硫代-3-硫酮-4,5-二硫代（dmt）和报道了具有中心离子In（III），Tl（III）和V（IV）的1,3-二硒基-2-硒酮-4,5-二硒酸酯（dsis）。在（Bu4N）2 [V（dmt）3]上进行了包含不对称配体的二硫代三螯合物的第一个X射线结构：该化合物结晶单斜的空间群P21 / c，在晶胞中有四个分子；a ＝ 16.264（3），b ＝ 17.319（4），c ＝ 21.554（4）A，β＝ 103.03（2）°。配体dmt导致[V（dmt）3] 2-中具有三个子配体的伪子午线排列的VS6部分的对称性非常低。
• Spectroscopic and electrical properties of [Cu4(dmit)3]2− and [Cu4(dsis)3]2− cluster anion complexes and their oxidized species (dmit=4,5-dimercapto-1,3-dithiole-2-thionate; dsis=4,5-di(hydroseleno)-1,3-diselenole-2-selonate)
  作者：Akito Yokozawa、Gen-etsu Matsubayashi

  DOI：10.1016/s0020-1693(00)85417-1

  日期：1991.8

  Abstract [Cu4(dmit)3]2− and [Cu4(dsis)3]2− (dmit=4,5-dimercapto-1,3-dithiole-2-thionate(2-); dsis=4,5-di(hydroseleno)-1,3-diselenole-2-selonate(2-)) cluster anion complexes, in which the anions consist of tetrahedron skeletons of copper atoms chelated and bridged by dmit-sulfur and dsis-selenium atoms, were prepared. Molecular interactions among the anion moieties through SS and SeSe contacts in

  摘要[Cu4（dmit）3] 2-和[Cu4（dsis）3] 2-（dmit = 4,5-dimercapto-1,3-dithiole-2-thionate（2-）; dsis = 4,5-di制备了（氢硒代）-1,3-二亚硒基-2-硬脂酸酯（2-））的阴离子配合物，其中阴离子由铜原子的四面体骨架所螯合，并被dmit-硫和dsis-硒原子桥接。从电子反射光谱推导了固体部分中通过SS和SeSe接触的阴离子部分之间的分子相互作用。它们被[FeCp2] +和[FeCp * 2] +阳离子（分别为Cp和Cp * =环戊二烯基和五甲基环戊二烯基阴离子）氧化，得到包含部分氧化的簇状阴离子部分的配合物。X射线光电子和ESR光谱证实了以配体为中心的氧化。
• Spectroscopic and electrical properties of the [W(C3Se5)3]2− anion complex (C3Se52− = 1,3-diselenole-2-selone-4,5-diselenolate) and the oxidized species
  作者：Katsuji Douki、Gen-etsu Matsubayashi

  DOI：10.1016/0020-1693(94)04291-3

  日期：1995.3

  tetrathiafulvalenium radical cation) in acetonitrile to afford the oxidized complexes [Fe(C 5 Me 5 ) 2 ] 0.5 [W(C 3 Se 5 ) 3 ], [NBu n 4 ] 0.1 [W(C 3 Se 5 ) 3 ] and [TTF] 0.5 [W(C 3 Se 5 ) 3 ], respectively. Current-controlled electrochemical oxidation of the complex in acetonitrile gave [NBu n 4 ] 0.6 [W(C 3 Se 5 ) 3 ]. The oxidized complexes exhibit electrical conductivities of 4.7×10 −5 −1.5×10 −3 S cm −1 at room

  摘要通过反应制备了[NBu n 4] 2 [W（C 3 Se 5）3]（C 3 Se 5 2- = 1,3-二硒烯-2-硒酮-4,5-二硒酸酯（2-））。在乙醇中用WCl 6溶解Na 2 [C 3 Se 5]，然后加入[NBu n 4] Br。二氯甲烷中的循环伏安图在-0.04和+0.03 V处显示两个氧化峰（相对于SCE）。该络合物在乙腈中与[Fe（C 5 Me 5）2] [BF 4]，碘或[TTF] 3 [BF 4] 2（TTF·+ =四硫富瓦烯鎓自由基阳离子）反应，得到氧化的络合物[Fe（ C 5 Me 5）2] 0.5 [W（C 3 Se 5）3]，[NBu n 4] 0.1 [W（C 3 Se 5）3]和[TTF] 0.5 [W（C 3 Se 5）3] ， 分别。在乙腈中对该配合物进行电流控制的电化学氧化，得到[NBu n 4] 0.6 [W（C 3 Se 5）3]。氧化的络合物显示出4
• Crystal structures of [NBun 4]2[M(C3S5)(C3Se5)](M = Ni or Pd) and properties of the nickel(II) complex
  作者：Gen-etsu Matsubayashi、Satoshi Tanaka、Akito Yokozawa

  DOI：10.1039/dt9920001827

  日期：——

  The complexes [NBun4]2[M(C3S5)(C3Se5)](M = Ni 1 or Pd 2) were isolated. Oxidation reactions of 1 with [Fe(C5H5)2][PF6], [Fe(C5Me5)2][BF4] and [ttf]3[BF4]2(ttf˙+= the radical cation of tetrathiafulvalene) and the current-controlled electrolysis of 1 afforded partially oxidized complexes [NBun4]0.7[Ni(C3S5)(C3Se5)], [Fe(C5Me5)2]0.7[Ni(C3S5)(C3Se5)], [ttf]0.7[Ni(C3S5)(C3Se5)] and [NBun4]0.3[Ni(C3S5)(C3Se5)]

  分离出配合物[NBu n 4 ] 2 [M（C 3 S 5）（C 3 Se 5）]（M ＝ Ni 1或Pd 2）。的氧化反应1用的[Fe（C 5 H ^ 5）2 ] [PF 6 ]，[铁（C 5我5）2 ] [BF 4 ]和[TTF] 3 [BF 4 ] 2（TTF + =的硫富瓦烯的自由基阳离子）和电流控制的电解1得到部分氧化的配合物[NBu n 4 ] 0.7 [Ni（C 3 S 5）（C 3 Se 5）]，[Fe（C 5 Me 5）2 ] 0.7 [Ni（C 3 S 5）（C 3 Se 5））]，[ttf] 0.7 [Ni（C 3 S 5）（C 3 Se 5）]和[NBu n 4 ] 0.3 [Ni（C 3 S 5）（C 3 Se 5））]， 分别。对于压实的颗粒，这些部分氧化的络合物在25°C下的电导率为4.2×10 –1 –5.5×10 –5 S cm –1。循环伏安法和电子吸收
• Olk, Ruth-Maria; Dietzsch, W.; Mattusch, J., Zeitschrift fur Anorganische und Allgemeine Chemie
  作者：Olk, Ruth-Maria、Dietzsch, W.、Mattusch, J.、Stach, J.、Nieke, Christine、et al.

  DOI：——

  日期：——