5H,10H-Dithiolo<2,3-b><2,5>benzodithiocin-2-one | 139197-47-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5H,10H-Dithiolo<2,3-b><2,5>benzodithiocin-2-one
• 英文别名: 5H,10H-dithiolo[2,3-b][2,5]benzothionine-2-one；o-xylenediyldithioethylene-1,3-dithiol-2-one；O=C(oxddt)；5,10-Dihydro-[1,3]dithiolo[4,5-c][2,5]benzodithiocin-2-one
• CAS: 139197-47-0
• 化学式: C₁₁H₈OS₄
• 分子量: 284.448
• InChiKey: QADQEUSEWOSMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5H,10H-Dithiolo<2,3-b><2,5>benzodithiocin-2-one 在 亚磷酸三乙酯 作用下， 反应 1.0h， 以18%的产率得到Bis(o-xylylenedithio)tetrathiafulvalene
  参考文献：
  名称：

  Kumar, S. Kalyan; Singh, Harkesh B.; Jasinski, Jerry P., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3341 - 3348

  摘要：

  DOI：
• 作为产物：
  描述：

  5H,10H-Dithiolo<2,3-b><2,5>benzodithiocine-2-thione 在 mercury(II) diacetate 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以52%的产率得到5H,10H-Dithiolo<2,3-b><2,5>benzodithiocin-2-one
  参考文献：
  名称：

  Kumar, S. Kalyan; Singh, Harkesh B.; Jasinski, Jerry P., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3341 - 3348

  摘要：

  DOI：

文献信息

• Square-planar metal dithiolene complexes (M=Ni, Au) exhibiting cis and trans forms based on structurally flexible o-xylylene backbone
  作者：Mitsushiro Nomura、Kazuto Harada、Toshinori Suzuki、Masatsugu Kajitani、Toru Sugiyama

  DOI：10.1016/j.poly.2012.08.026

  日期：2012.10

  The square-planar metal dithiolene complexes of o-xylenediyldithioethylene-1,2-dithiolate (oxddt) ligand, (Et4P)[Ni(oxddt)(2)] (1), (Ph4P)[Ni(oxddt)(2)] (2) and (Ph4P)[Au(oxddt)(2)] (3), were prepared and characterized. Among them, the Ni complexes 1 and 2 showed cis-anti-form structures, whose two benzene rings of the Ni(oxddt)(2) molecule are closely located to the dithiolene rings but located on the opposite side with respect to the dithiolene ring. In contrast to these Ni complexes, the Au complex 3 has a trans-anti form, suggesting that a Ni/Au substitution in the [M(oxddt)(2)] modifies those molecular structures in the crystals. An intramolecular pi orbital overlap at the alpha-LUMO + 5 level between benzene and dithiolene rings was observed in the [Ni(oxddt)(2)] complex with the cis-anti-form. Redox behavior of 1 and 3 were investigated by cyclic voltammetry measurements. (C) 2012 Elsevier Ltd. All rights reserved.
• Preparation spectroscopy and conductivity of [Pt(SS)(NN)]-type complexes and their iodine oxidized complexes
  作者：Zhifeng Hao、Zongxun Tang、Qizhen Shi

  DOI：10.1016/s0020-1693(98)00259-x

  日期：1999.1

  Complexes of the general formula [Pt(SS)(NN)] have been prepared, where SS is bbdt(1,2-bis(benzylthio)ethylene-1,2-dithiolate) or dpdt (5,6-dihydrophenyl-1,4-dithion-2,3-dithiolate) and NN is bipy (2,2'-bipyridine) or phen (1,10-phenanthroline). The UV-Vis spectra exhibit intense intramolecular ligand-to-ligand charge transfer absorption bands at 440-600 nm. Cyclic voltammograms show a reversible oxidation step assigned to [Pt(SS)(NN)](0)/[Pt(SS)(NN)](+). On doping iodine into the complexes, partial oxidation occurs to afford [Pt(SS)(NN)I-x (x=1.9(2.2). IR, Raman and ESR spectra of the iodine-doped complexes are discussed. Electrical conductivities of the neutral mixed-ligand complexes (10(-9)-10(-10) S cm(-1)) increase to 10(-6)-10(-7) S cm(-1) upon It doping. (C) 1999 Elsevier Science S.A. All rights reserved.
• CpCo(dithiolene) complexes of highly flexible oxddt ligand with two different Z-shaped and U-shaped structures
  作者：Mitsushiro Nomura、Daisuke Takeuchi、Yoshiko Toyota、Eriko Suzuki、Chikako Fujita-Takayama、Toru Sugiyama、Masatsugu Kajitani

  DOI：10.1016/j.jorganchem.2009.07.026

  日期：2009.12

  [CpCo(oxddt)] complex (2, oxddt = o-xylenediyldithioethylene-1,2-dithiolate, Cp = eta(5)-cyclopentadienyl) was obtained from o-xylenediyldithioethylene-1,3-dithiol-2-one (O=C(oxddt)) (1). 2 further reacted with diazoalkanes (N2CHR) to form some alkylidene-bridged adducts [CpCo(CHR)(oxddt)] (R = H (3a), SiMe3 (3b)). Adduct 3a further reacted with protic acids (HX) to give some S-methylated adducts [CpCo(X)(oxddt)(S-Me)] (X = Cl (4a), OCOCF3 (4c)), followed by the Co-C bond cleavage in the three-membered cobaltathiirane ring. Two different Z-shaped and U-shaped molecular structures were observed by X-ray diffraction studies. In the former structure (Z), the dithiolene and o-xylylene planes are located at almost parallel position each other, and in the latter structure (U), both planes are not parallel but the o-xylylene moiety is located closer to the dithiolene plane than the Z-shaped one. The Z-shaped structure involves 1 and 2. The U-shaped structure involves 3a, 3b, 4a and 4c. Complex 1 showed a one-dimensional chain through intermolecular pi-pi interaction in the crystal. Complex 2 had a dimeric interaction between dithioethylenedithiolate moieties (S2C2S2) in the oxddt. The SiMe3 group in 3b was placed at an exo-position with respect to the cobaltadithiolene ring due to a steric hindrance from the U-shaped oxddt ligand. In 4a, the X and Me groups are located at the opposite side of the dithiolene plane (anti-form) but in 4c, both groups are presented at the same side of the dithiolene plane (syn-form). The NMR analysis of 4a in solution indicated existence of both anti-and syn-isomers (7:1). (C) 2009 Elsevier B.V. All rights reserved.