5-(pyridin-3-yl)-3H-1,2-dithiole-3-thione | 104792-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(pyridin-3-yl)-3H-1,2-dithiole-3-thione
• 英文别名: 5-Pyridin-3-yldithiole-3-thione
• CAS: 104792-16-7
• 化学式: C₈H₅NS₃
• 分子量: 211.332
• InChiKey: CLIUBDBIYFDQNP-UHFFFAOYSA-N

物化性质

• 沸点：
  395.9±52.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl-3-hydroxy-3-(3-pyridyl)-2-propenedithioate 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 indium(III) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以86%的产率得到5-(pyridin-3-yl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Switching Selectivity of α-Enolic Dithioesters: One Pot Access to Functionalized 1,2- and 1,3-Dithioles

  摘要：

  An operationally simple cascade protocol has been developed for the construction of 1,2- and 1,3-dithiole derivatives from alpha-enolic dithio esters. 1,2-Dithioles are achieved by the reaction of dithioesters with elemental sulfur in the presence of InCl3 under solvent-free conditions. 1,3-Dithioles have been constructed via DABCO mediated self coupling of dithioesters in open air enabling the formation of two new C-S bonds and one ring in a single operation in contiguous fashion. The reactions proceeded smoothly affording the desired sulfur-rich heterocycles in good to excellent yields, exhibiting gram-scale ability and broad functional group tolerance utilizing easy to handle cheap and easily available reagents. The probable mechanisms for the formation of suggested. 1,2- and 1,3-dithioles from alpha-enolic dithioesters have been suggested.

  DOI：

  10.1021/acs.joc.6b01802

文献信息

• Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C–N Bond Cleavage
  作者：Hong-Hui Xu、Xiao-Hong Zhang、Xing-Guo Zhang

  DOI：10.1021/acs.joc.9b00685

  日期：2019.6.21

  oxidative sulfuration and annulation of propargylamines with elemental sulfur is described. The tandem reaction involves C–N bond cleavage and the formation of multiple C–S bonds, affording 1,2-dithiole-3-thiones in good to excellent yields with good functional group tolerance.

  描述了铜催化的好氧氧化硫化和炔丙胺与元素硫的环化。串联反应涉及C–N键断裂和多个C–S键的形成，从而以良好的收率和优异的收率提供了1,2-二硫代3-硫酮，并且具有良好的官能团耐受性。
• 铜催化苯丙炔胺硫环化合成1,2-二硫-3-硫酮 衍生物的方法
  申请人：温州大学

  公开号：CN109776489B

  公开（公告）日：2021-03-30

  本发明涉及一种铜催化炔丙胺硫环化合成1,2‑二硫‑3‑硫酮衍生物的方法，以N,N‑二甲基‑3‑苯基丙‑2‑炔‑1‑胺为底物，通过在底物中加入氯化亚铜、溴化亚铜或碘化亚铜作为催化剂，磷酸钾、碳酸氢钠或醋酸钠作为碱，单质硫作为硫源在溶剂中，于100‑120℃下，搅拌反应12小时。本发明使用单质硫作为硫源，具有原料简单易得，反应操作简单、条件相对温和、底物普适性广、产率较高、官能团兼容性良好的优点。
• 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.
• US9370504B2
  申请人：——

  公开号：US9370504B2

  公开（公告）日：2016-06-21