4,9-dioxo-4.9-dihydronaphtho[2,3-d]-1,3-dithiole-2-thione | 65160-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,9-dioxo-4.9-dihydronaphtho[2,3-d]-1,3-dithiole-2-thione
• 英文别名: 4,9-dioxo-4,9-dihydronaphtho[2,3-d]-1,3-dithiole-2-one；benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione；1,4-dioxonaphtho-[2,3-b]-1,3-dithiol-2-thione；2-thioxo-naphtho[2,3-d][1,3]dithiole-4,9-dione；2-Sulfanylidenebenzo[f][1,3]benzodithiole-4,9-dione
• CAS: 65160-10-3
• 化学式: C₁₁H₄O₂S₃
• 分子量: 264.35
• InChiKey: QAIGZEYLNKIMAV-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C
• 沸点：
  433.1±55.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4,9-dioxo-4.9-dihydronaphtho[2,3-d]-1,3-dithiole-2-thione 在 吡啶 、 sodium dithionite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 1,4-dihydroxynaphthyl-1,2-thiole-2-thione hexanoate
  参考文献：
  名称：

  Tetrathiafulvalene quinones, hydroquinones and esters

  摘要：

  Benzocyclohexa-2,5-diene-1,4-dione-1,3-thiole-2-thione (2) was synthesized starting with 2,3-dichloronapthoquinone (1). Compounds 3 and 4 were also obtained; however, the yield of 2 can be increased through control of the temperature and reaction time. Reaction of 2 with triethylphosphite gave 5 and the tetrathiafulvalene ester 6. The tetrathiafulvalenequinone (9) was obtained by hydrolysis of 6 followed by oxidation of & Compound 9 was obtained more directly by hydrogenation of 2 followed by coupling with triethylphosphite and oxidation. Chloranil was used to prepare the dithiafulvene quinone 12 which was reduced, coupled with triethylphosphite to form, presumably, polymer 13. The reactions were repeated using the hexanoic acid esters of the corresponding hydroquinone thiafulvalenes. The crystal structures of 2, 3, 4, 5, 6a and 10 were determined by X-ray diffraction. Cyclic voltammetry studies show the tetrathiafulvalene quinones reduce like quinones, but do not exhibit the oxidation properties of tetrathiafulvalenes.

  DOI：

  10.1016/s0040-4020(01)89885-9
• 作为产物：
  描述：

  (4,9-dioxo-4,9-dihydro-naphtho[2,3-d][1,3]dithiol-2-ylidene)-dimethyl-ammonium; chloride 生成 4,9-dioxo-4.9-dihydronaphtho[2,3-d]-1,3-dithiole-2-thione
  参考文献：
  名称：

  MUKAI, TOSIO;YAMASITA, KEHJRO;SUDZUKI, TAKAKI

  摘要：

  DOI：

文献信息

• Novel Fused D−A Dyad and A−D−A Triad Incorporating Tetrathiafulvalene and <i>p</i>-Benzoquinone
  作者：Frédéric Dumur、Nicolas Gautier、Nuria Gallego-Planas、Yücel Şahin、Eric Levillain、Nicolas Mercier、Piétrick Hudhomme、Matteo Masino、Alberto Girlando、Vega Lloveras、José Vidal-Gancedo、Jaume Veciana、Concepció Rovira

  DOI：10.1021/jo035689f

  日期：2004.3.1

  compounds of the cation radical and anion radical obtained upon (electro)chemical oxidation and reduction, respectively, was monitored by optical and ESR spectroscopies. The anion radical Q−TTF−Q-• triad was demonstrated to be a class II mixed-valence system with the existence of a temperature-dependent intramolecular electron transfer. The crystallographic tendency of these fused systems to overlap in

  新型融合的供体-受体二元体（TTF-Q或D-A）和受体-供体-受体三联体（Q-TTF-Q或A-D-A）结合了供体四硫富瓦烯（TTF）和受体对苯并醌（Q ）已合成。这些分子的溶液紫外可见光谱显示出低能量吸收带，这归因于两个拮抗单元之间的分子内电荷转移。通过循环伏安法显示了供体和受体部分可逆的氧化和还原波的存在，与TTF /醌单元的比例一致。通过光学和ESR光谱法监测由这些化合物分别在（电）化学氧化和还原时获得的阳离子自由基和阴离子自由基的连续生成。该阴离子自由基Q-TTF-Q - •三单元组被证明是具有温度依赖性分子内电子转移的II类混合价体系。还讨论了这些熔融系统在交替的A-D-A单元的混合堆栈中重叠的晶体学趋势。
• Preparation and Characterization of a π-Conjugated Donor–Accepter-type Ligand Molecule with Redox Abilities
  作者：Keiichi Katoh、Naoki Sato

  DOI：10.1246/cl.2008.618

  日期：2008.6.5

  We have synthesized a zwitterion-like molecule 1 having an N,N,N-tridentate ligand site for metal complexation. Compound 1 exhibited negative solvatochromism of the intramolecular charge-transfer (ICT) band in its UV–visible absorption spectrum for different polarity of solvents. Its anion radical (1−•) was generated from both electrical and chemical reduction of the p-naphthoquinone moiety.

  我们合成了一种类似双性离子的分子1，具有N,N,N-三齿配体位点以便于金属配合。化合物1在其紫外-可见吸收光谱中表现出随着溶剂极性的不同而发生的负溶剂色效应（ICT带）。其阴离子自由基（1−•）是通过对p-萘醌基团进行电化学和化学还原生成的。
• Coupling Tetracyanoquinodimethane to Tetrathiafulvalene: A Fused TCNQ-TTF-TCNQ Triad
  作者：Francisco Otón、Vega Lloveras、Marta Mas-Torrent、José Vidal-Gancedo、Jaume Veciana、Concepció Rovira

  DOI：10.1002/anie.201104841

  日期：2011.11.11

  Happy marriage: For the first time, a fused TCNQ–TTF–TCNQ triad has been synthesized and structurally characterized. Strong bending is observed in both the TTF bridge and the benzo‐TCNQ moieties, which prevents good packing for intermolecular charge transfer. The Vis/NIR and VT‐EPR studies of the mixed‐valence derivative of the triad indicate that the electrons are moving from one acceptor moiety to

  幸福的婚姻：第一次，融合了TCNQ-TTF-TCNQ三合一并在结构上进行了表征。在TTF桥和苯并TCNQ部分均观察到强烈弯曲，这妨碍了分子间电荷转移的良好堆积。三合一混合价导数的Vis / NIR和VT-EPR研究表明，电子通过供体TTF桥从一个受主部分移动到另一个受主部分。
• Efficient access to naphthoquinon-1,3-dithioles: formal cycloaddition and oxidation of quinones and amines with CS 2
  作者：Huan-ming Huang、Yu-jin Li、Jian-rong Yang、Jian-hong Jia、Qing Ye、Liang Han、Jian-rong Gao

  DOI：10.1016/j.tet.2013.04.050

  日期：2013.6

  An efficient strategy for one-pot synthesis of a variety of naphthoquinon-1,3-dithiole derivatives has been developed. The combined action of the formal cycloaddition and oxidation reaction of quinones and amines in the presence of CS2 without additional oxidant produced naphthoquinon-1,3-dithiole derivatives in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• DEMETRIADIS N. G.; HUANG S. J.; SAMULSKI E. T., TETRAHEDRON LETT. <TELE-AY>, 1977, NO 26, 2223-2226
  作者：DEMETRIADIS N. G.、 HUANG S. J.、 SAMULSKI E. T.

  DOI：——

  日期：——