4,5-bis(benzylthio)-1,3-dithiole-2-thione | 54995-25-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,5-bis(benzylthio)-1,3-dithiole-2-thione
• 英文别名: 4,5-bis(benzylthio)-1,3-dithione-2-thione；4,5-bis(benzylthio)-1,3-dithiol-2-thione；4,5-(thiobenzoyl)-1,3-dithiol-2-thione；bis(benzoylthio)-1,3-dithiole-2-thione；4,5-bis-benzylsulfanyl-[1,3]dithiole-2-thione；1,3-Dithiole-2-thione, 4,5-bis[(phenylmethyl)thio]-；4,5-bis(benzylsulfanyl)-1,3-dithiole-2-thione
• CAS: 54995-25-4
• 化学式: C₁₇H₁₄S₅
• mdl: MFCD01230520
• 分子量: 378.628
• InChiKey: NVVXRRUEMAPHNY-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  510.5±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二氯(DPPE)二金(I) 、 4,5-bis(benzylthio)-1,3-dithiole-2-thione 在 Na 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到[Au2(μ-1,3-dithiole-2-thione-4,5-dithiolate)(μ-dppe)]
  参考文献：
  名称：

  具有C3S52-配体的九元和十元二氮杂环。NBu4 [Au2（μ-C3S5）（μ-CH2PPh2，CH2）]的晶体结构

  摘要：

  摘要已通过不同方法测试了具有C3S52-（1,3-二硫代-2-硫酮-4,5-二硫代）配体的杂桥双核金（I）配合物的合成：（i）[Au（ μ-LL）X2] n-和Na2C3S5乙醇溶液；（ii）[Au2（C3S5）（AsPh3）] n与不同双齿配体的反应。生成的配合物Q [Au2（μ-C3S5）（μ-CH2PPh2CH2）]（1），[Au2（μ-C3S5）（μ-dppe）]（2）和Q [Au2（C3S5）S2CNR2）] [R = Me（3），Et（4）或CH2Ph（5））已通过分析，电导率，IR，31P和1H NMR进行了表征。络合物（PPN）2 [Au（C3S5）2] 2]（6）（PPN = N（PPh3）2）是通过[AuCl（tht）]（tht =四氢噻吩）或[AuCl（AsPh3）]反应而获得的用Na 2 C 3 S 5和添加（PPN）Cl。1与（TTF）3（BF4）2（TTF =四

  DOI：

  10.1016/0020-1693(96)05088-8
• 作为产物：
  描述：

  氯化苄 、 alkaline earth salt of/the/ methylsulfuric acid 以 丙酮 为溶剂， 反应 16.0h， 以82%的产率得到4,5-bis(benzylthio)-1,3-dithiole-2-thione
  参考文献：
  名称：

  Third-Order Nonlinear Optical Properties of Sulfur-Rich Compounds

  摘要：

  The molecular third-order optical nonlinearity gamma(R) (second hyperpolarizability or nonlinear refractive index) was measured for a series of sulfur-rich molecules: sulfur (Ss), carbon-sulfur compounds, and metal thiolate clusters. Z-scan techniques (pulse width 27 ps, wavelength 527 nm) were used to measure these properties in solution by comparing the solution to the pure solvent. Our approach is an efficient way to evaluate a number of different compounds and to quickly direct synthetic strategies for improved nonlinear and linear optical properties. The optical nonlinearities were evaluated in terms of figures of merit, \W\I-0 and [T](-1), where \W\I-0 is the ratio of nonlinear refraction to linear absorption and [T](-1) is the ratio of nonlinear refraction to nonlinear absorption. Among the carbon-sulfur compounds, C6S8O2 had the largest figures of merit: /W/I-0 = 4.3 x 10(-13) m(2) W-1 and [T](-1) > 5. The metal thiolate cluster with the largest second hyperpolarizability was [Zn10S4(SPh)(16)](4-) (gamma(R) = -7.8 x 10(-56) C m(4) V-3, -6.3 x 10(-31) esu). This cluster exhibited no measurable linear or nonlinear absorption, so the figures of merit were effectively infinite. Previous work on the second hyperpolarizability of sulfur-rich compounds examined species that were hampered by substantial linear absorption coefficients. The present work shows that high figures of merit can be achieved without significant linear or nonlinear absorption.

  DOI：

  10.1021/jp990137f

文献信息

• A new D-A derivative with a 1,3-dithiol-2-ylidene unit: Structural, spectroscopic and theoretical studies
  作者：Yu-Lan Zhu、Kui-Rong Ma、Qi-Fan Yin、Xu-Dong Zhong、Li Cao

  DOI：10.1016/j.poly.2013.06.056

  日期：2013.10

  Abstract A novel D-A compound, [Cu(L)2Cl2]·2CH2Cl2 ML, has been synthesized based on 4′,5′-diaza-9′-(4,5-bis(benzylthio)-1,3-dithiole-2-ylidene)-fluorene ((C11N2H6)(C3S2)(SCH2C6H5)2, L). Both ML and L are further characterized by elemental analysis, IR, 1H and 13C NMR. Single-crystal X-ray diffraction shows ML displays a 3-D supramolecular network built by the neutral mononuclear unit [Cu(L)2Cl2] via

  摘要基于4'，5'-diaza-9'-（4,5-双（苄硫基）-1,3-二硫醇-2）合成了一种新型的DA化合物[Cu（L）2Cl2]·2CH2Cl2 ML。 -亚苯基）-芴（（C11N2H6）（C3S2）（SCH2C6H5）2，L）。ML和L均通过元素分析，IR，1H和13C NMR进一步表征。单晶X射线衍射显示ML显示了由中性单核单元[Cu（L）2Cl2]通过氢键，π-π堆积和S⋯S相互作用建立的3-D超分子网络。UV-Vis光谱显示，与L（415 nm）相比，ML的最低能量吸收带（431 nm）发生了红移。电化学行为表明，虽然L与Cu2 +离子配位会降低ML的HOMO含量，但氧化电位却会增加（1.19至1.37 V）。光电流测量表明，L的分子内电荷转移（ICT）应该比ML容易。通过DFT计算获得的重组能的结果（λi：L的0.25 eV，ML的0.82 eV）表明，较低的重组能对L内的载流
• A New Approach to 4-Alkylthio-1,3-dithiole-2-thione:  An Unusual Reaction of a Zinc Complex of 1,3-Dithole-2-thione-4,5-dithiolate
  作者：Chunyang Jia、Deqing Zhang、Wei Xu、Daoben Zhu

  DOI：10.1021/ol015990n

  日期：2001.6.1

  [see reaction]. A new and facile approach to 4-alkylthio-1,3-dithiole-2-thione starting from easily accessible reactants was described. This approach was based on the unusual reaction of a zinc complex of 1,3-dithiole-2-thione-4,5-dithiolate with electrophilic reagents in the presence of 3-picolyl chloride hydrochloride/or 4-picolyl chloride hydrochloride/or pyridine hydrochloride.

  [请参阅反应]。描述了一种从容易获得的反应物开始的4-烷硫基1,3-二硫基-2-硫酮的简便方法。该方法基于1,3-二巯基-2-硫酮-4,5-二硫醇盐的锌络合物与亲电子试剂在3-甲基吡啶氯盐酸盐/或4-甲基吡啶氯盐酸盐/或吡啶存在下的异常反应盐酸盐。
• Srivastav, Manish K.; Saraswat, Apoorv; Sharma, Laxmi Kant, Journal of the Indian Chemical Society, 2010, vol. 87, # 9, p. 1131 - 1135
  作者：Srivastav, Manish K.、Saraswat, Apoorv、Sharma, Laxmi Kant、Singh

  DOI：——

  日期：——
• Falsig, Mogens; Lund, Henning, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 8, p. 591 - 596
  作者：Falsig, Mogens、Lund, Henning

  DOI：——

  日期：——
• Synthesis and Reactivity of Heteroleptic Complexes of Gold with 2-Thioxo-1,3-dithiole-4,5-dithiolate (dmit). X-ray Structure of [Au₂(μ-dmit)(PPh₃)₂], (NBu₄)[Au(dmit)(PPh₃)], and (PPN)[Au(dmit)(C₆F₅)₂]
  作者：Elena Cerrada、Peter G. Jones、Antonio Laguna、Mariano Laguna

  DOI：10.1021/ic950893+

  日期：1996.1.1

  The reactions of Na(2)dmit (dmit = 2-thioxo-1,3-dithiole-4,5-dithiolate) with AuClL in 1:2 ratios lead to [Au-2(dmit)L(2)] [L = PPh(3) (1), PPh(2)Me (2), PPhMe(2) (3), PMe(3) (4), CH(2)PPh(3) (5), CH(2)PPh(2)Me (6), CH(2)PPhMe(2) (7)]. Complexes 1, 2, and 5 react further with equimolecular amounts of [AuL(tht)]ClO4 (tht = tetrahydrothiophene), affording trinuclear complexes [Au-3(dmit)L(3)]ClO4 (8-10). When the reactions of Na(2)dmit with AuClL are carried out in 1:1 ratios and in the presence of NBu(4)Br, mononuclear tricoordinated gold(I) complexes NBu(4)[Au(dmit)L] [L = PPh(3) (11), PPh(2)Me (12), PMe(3) (13)] are obtained. Other anionic derivatives such as (PPN)(2)[Au-2(dmit)X(2)] [X = C6F5 (14), Cl (15a) Br (15b)] can be obtained either by reaction of Na(2)dmit with Q[Au(C6F5)X] in 1:2 ratio or by addition of (PPN)X to the recently reported [Au-2(dmit)(AsPh(3))]. Oxidative reactions of 11, 12, and 14 or 15b with excess (TTF)(3)(BF4)(2) afford (TTF)(2)[Au(dmit)(2)] (16), (TTF)[Au-2(dmit)(C6F5)(2)] (17), and (TTF)(3)[Au-2(dmit)Br-2] (18), respectively. Reaction of complex 14 with TCNQ gives the anionic gold(III) complex [Au(dmit)(C6F5)(2)](-) (19). Electrical conductivities of these complexes at room temperature in compacted pellets are 2 x 10(-3) (16), 7 x 10(-5) (17), and 2 x 10(-2) (18) S . cm(-1). Electrocrystallization of 1 and 11 affords [Au-2(dmit)(2)(PPh(3))] (20) and the known NBu(4)[Au(dmit)(2)], respectively. X-ray structure determinations were performed for complexes 1, 11, and 19b.