5-ethyl-3H-1,2-dithiole-3-thione | 52514-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 英文名称: 5-ethyl-3H-1,2-dithiole-3-thione
• 英文别名: 5-ethyl-[1,2]dithiol-3-thione；5-Aethyl-[1,2]dithiol-3-thion；5-Ethyl-1,2-dithiole-3-thione；5-ethyldithiole-3-thione
• CAS: 52514-89-3
• 化学式: C₅H₆S₃
• 分子量: 162.301
• InChiKey: GUBILWKWWKEJGX-UHFFFAOYSA-N

物化性质

• 熔点：
  21 °C
• 沸点：
  96-99 °C(Press: 0.02 Torr)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-戊烯 在 sulfur 作用下， 生成 5-ethyl-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Broun et al., Zhurnal Obshchei Khimii, 1950, vol. 20, p. 726,729;engl.Ausg.S.765

  摘要：

  DOI：

文献信息

• Thionation with the Reagent Combination of Phosphorus Pentasulfide and Hexamethyldisiloxane
  作者：Thomas J. Curphey

  DOI：10.1021/jo0256742

  日期：2002.9.1

  The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts

  P4S10和六甲基二硅氧烷的组合可将酯，内酯，酰胺，内酰胺和酮有效地转化为其相应的硫代衍生物。在元素硫的存在下，该试剂将3-氧代酯转化为二硫代硫酮。产率与使用劳森试剂获得的产率相当或更高。该方法的优点在于，可以通过简单的水解后处理或通过硅胶过滤而不是通过劳氏试剂所要求的色谱法来除去试剂衍生的副产物。
• Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization
  作者：Thomas J. Curphey、H.Howard Joyner

  DOI：10.1016/s0040-4039(00)79295-1

  日期：1993.11

  Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.
• Dianions of 3-oxodithioic acids: preparation and conversion to 3H-1,2-dithiole-3-thiones
  作者：Thomas J. Curphey、Adam H. Libby

  DOI：10.1016/s0040-4039(00)01191-6

  日期：2000.9

  Reaction of ketones with CS2 and 2 equivalents of KH in THF-N,N'-dimethylpropyleneurea solution produces the dianions of 3-oxodithioic acids. These dianions are converted in good yield to 3H-1,2-dithiole-3-thiones by the sequential action of hexamethyldisilathiane and an oxidizing agent such as hexachloroethane. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Legrand; Lozac'h, Bulletin de la Societe Chimique de France, 1955, p. 79,83
  作者：Legrand、Lozac'h

  DOI：——

  日期：——
• Synthesis and structure–activity relationships study of dithiolethiones as inducers of glutathione in the SH-SY5Y neuroblastoma cell line
  作者：Dennis A. Brown、Swati Betharia、Jui-Hung Yen、Quang Tran、Hitesh Mistry、Kari Smith

  DOI：10.1016/j.bmcl.2014.10.005

  日期：2014.12

  Parkinson's disease is a neurodegenerative disorder that involves the degeneration of nigrostriatal dopaminergic neurons. Elevated levels of reactive oxygen species have been shown to deplete cellular levels of the ubiquitous antioxidant glutathione, leading to oxidative stress and eventual neuronal cell death. Dithiolethiones, a class of sulfur-containing heterocyclic molecules, have been shown to induce cellular production of glutathione in a variety of tissues, but have not been extensively evaluated in neurons. Herein, we report the synthesis and preliminary structure-activity relationships study of several substituted dithiolethiones. Three molecules were identified (D3T, CPDT, and 2d) that potently induced cellular glutathione in the SH-SY5Y neuroblastoma cell line. Furthermore, these compounds were found to provide neuroprotection in the 6-hydroxydopamine model of neurotoxicity. This study suggests that dithiolethione-mediated neuroprotection may have potential as a disease-modifying antiparkinsonian therapy. (C) 2014 Elsevier Ltd. All rights reserved.