4,5-二苯基-3H-1,2-二硫杂环戊烯-3-硫酮 | 13232-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4,5-二苯基-3H-1,2-二硫杂环戊烯-3-硫酮
• 英文名称: 4,5-diphenyl-[1,2]dithiole-3-thione
• 英文别名: 4,5-Diphenyl-3H-1,2-dithiol-3-thion；4,5-diphenyl-3H-1,2-dithiole-3-thione；4,5-diphenyl-1,2-dithiol-3-thione；4,5-Diphenyl-1,2-dithiol-3-thion；4,5-diphenyldithiole-3-thione
• CAS: 13232-76-3
• 化学式: C₁₅H₁₀S₃
• 分子量: 286.442
• InChiKey: ILAXRAVUQIJKLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4,5-二苯基-3H-1,2-二硫杂环戊烯-3-硫酮 在 碘甲烷 作用下， 生成 3-(Methylthio)-4,5-diphenyl-1,2-dithiolium-iodid
  参考文献：
  名称：

  Woronkow; Broun; Karpenko, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1927,1939

  摘要：

  DOI：
• 作为产物：
  描述：

  胆维他 以 xylene 为溶剂， 反应 18.0h， 生成 4,5-二苯基-3H-1,2-二硫杂环戊烯-3-硫酮
  参考文献：
  名称：

  Behringer, Hans; Meinetsberger, Eike, Liebigs Annalen der Chemie, 1982, # 2, p. 315 - 341

  摘要：

  DOI：

文献信息

• Selective [3 + 2] Cycloaddition of Cyclopropenone Derivatives and Elemental Chalcogens
  作者：Jian Wu、Wen-Xia Gao、Xiao-Bo Huang、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1021/acs.orglett.0c01914

  日期：2020.7.17

  A highly efficient method is disclosed for the synthesis of 1,2-dichalcogen heterocycles via [3 + 2] cycloaddition of cyclopropenone derivatives and elemental chalcogens. Different from other cyclopropenone derivatives, cyclopropenselenones undergo unprecedented rearrangement with elemental sulfur. The features of this protocol include mild reaction conditions, high efficiency, excellent atom economy

  公开了一种通过环丙烯酮衍生物和元素硫属元素的[3 + 2]环加成合成1,2-二氢杂环的高效方法。与其他环丙烯酮衍生物不同，环丙烯酮与元素硫会经历前所未有的重排。该方案的特点包括反应条件温和，效率高，原子经济性好，克级能力和良好的区域选择性。
• Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments
  作者：Jessica J. Sánchez García、Rene S. Joo-Cisneros、David García-Bassoco、Marcos Flores-Alamo、José M. Méndez Stivalet、Jesús García-Valdés、Elena I. Klimova

  DOI：10.1016/j.jorganchem.2021.121809

  日期：2021.7

  A new synthesis method was established for 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones, from different cyclopropenones: diphenyl (a), bis-(4-methoxyphenyl (b), diferrocenyl (c) and diruthenocenyl (d), in the presence of elemental sulfur with yields of the 5a-d (35-57%), or in the presence of the additive NaHS, with yields of the 5a-d (45-72%) and 6a-d (10-18%). The characterization of the new compounds

  建立了一种新的合成方法，用于合成来自不同环丙烯的1,2-二硫醇-3-酮和1,2-二硫醇-3-硫酮：二苯基（a），双-（4-甲氧基苯基（b），二铁茂铁（c）和diruthenocenyl（d），在元素硫的存在下与所述的收率图5a-d（35-57％），或在添加剂硫氢化钠的存在下，与所述的收率图5a-d（45-72％）和6a中-d（10-18％）。通过IR，1 H和13 C NMR光谱，元素分析，质谱对新化合物进行表征，此外，对化合物5a，b， d进行了。使用循环（CV），微分脉冲（DPV）和方波（SWV）伏安法研究了杂环化合物的氧化还原特性。
• Thermolysis of 1, 3-dithiol-2-yl azides and thermal properties of the resulting 1,4,2-dithiazines
  作者：Juzo Nakayama、Atsuhiro Sakai、Akira Tokiyama、Masamatsu Hoshino

  DOI：10.1016/s0040-4039(00)94520-9

  日期：1983.1

  azides, on thermolysis in refluxing toluene, give 3-substituted 1,4,2-dithiazines which thermally extrude sulfur atom of the 4-position selectively to yield 3-substituted isothiazoles, while 2-unsubstituted 1,3-dithiol-2-yl azides undergo both ring expansion yielding 1,4,2-dithiazines and peculiar thermal dissociation into 1,3-dithiol-2-ylidene carbenes and hydrogen azide.

  在回流的甲苯中热解后，将2-取代的1,3-二硫醇-2-基叠氮化物生成3-取代的1,4,2-二噻嗪，其选择性地热挤出4-位的硫原子，从而生成3-取代的异噻唑，而2-未取代的1,3-二硫醇-2-基叠氮化物均经历扩环反应，生成1,4,2-二噻嗪，并且发生特殊的热解离反应，生成1,3-二硫醇-2-亚基苯甲酸酯和叠氮化氢。
• Expedient sulfurization with elemental sulfur and an unexpected conversion of 2,3-diarylcyclopropenethiones using tetrabutylammonium fluoride (TBAF) as a source of the fluoride anion
  作者：Grzegorz Mlostoń、Jakub Wręczycki、Amelia Robak、Katarzyna Urbaniak、Dariusz M. Bieliński、Marcin Palusiak、Szymon Sutuła、Krzysztof Woźniak、Heinz Heimgartner

  DOI：10.1016/j.jfluchem.2023.110170

  日期：2023.8

  Elemental sulfur, upon treatment with tetrabutylammonium fluoride (TBAF, 20 mol%) in THF solution at room temperature, undergoes activation via ring opening, leading to in situ-generation of the red colored, highly reactive fluoropolysulfide anion FSx‒. The latter easily reacts with sterically congested 2,3-diarylcyclopropenethiones and five membered 3H-1,2-dithiole-3-thiones are formed selectively

  在室温下，元素硫在 THF 溶液中用四丁基氟化铵（TBAF，20 mol%）处理后，通过开环进行活化，导致原位生成红色、高反应性的氟多硫化物阴离子 FS x –。后者很容易与空间拥挤的2,3-二芳基环丙烯硫酮反应，并以良好至优异的产率选择性地以单一产物形式形成五元3 H -1,2-二硫醇-3-硫酮。在 2,3-双(4-氯苯基)环丙烯酮的情况下观察到通过扩环的类似硫化过程，并且在这种情况下预期的 3 H分离出-1,2-二硫醇-3-酮衍生物，收率83%。详细的方案可以取代已经报道的不太方便的程序，基于 DMF 作为溶剂和氟化钾作为活化剂的应用。在不存在硫的情况下用 TBAF 处理 2,3-二苯基环丙烯硫酮，意外地形成了二聚 α-苯甲酰硫烯酮（去磺胺）的( E,Z )- 和 ( Z,Z )-异构体，并且初步的机制涉及假设最初形成的反应性（α-硫烯酮）苯基亚甲基（一种卡宾物质）作为关键中间体参与其中。
• Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
  作者：Zi-Long Song、Feifei Bai、Baoxin Zhang、Jianguo Fang

  DOI：10.1021/acs.jafc.9b06360

  日期：2020.2.19

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.