3H-1,2-二硫杂环戊二烯-3-硫酮 | 534-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫醇
• 中文名称: 3H-1,2-二硫杂环戊二烯-3-硫酮
• 英文名称: 1,2-Dithiole-3-thione
• 英文别名: 3H-1,2-dithiole-3-thione；dithiole-3-thione
• CAS: 534-25-8
• 化学式: C₃H₂S₃
• mdl: MFCD00961788
• 分子量: 134.247
• InChiKey: LZENMJMJWQSSNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81°C
• 沸点：
  47 °C(Press: 0.1 Torr)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Solid
• 碰撞截面：
  120.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  3H-1,2-二硫杂环戊二烯-3-硫酮 生成 thioformyl thioketene
  参考文献：
  名称：

  1,2-二硫代-3-硫酮的快速真空热解形成1,2-丙二烯-1,3-二硫酮（亚硫化碳）

  摘要：

  通过在800-1000°C的温度范围内对烷基硫取代的1,2-二硫代-3-硫酮进行快速真空热解，可得到1,2-丙二烯-1,3-二硫酮（亚硫化碳）。分离出二硫酮，并在10K的氩气基质中进行表征。

  DOI：

  10.1016/0040-4039(96)00941-0
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 在 吡啶 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 tetraphosphorus decasulfide 作用下， 以69.6%的产率得到3H-1,2-二硫杂环戊二烯-3-硫酮
  参考文献：
  名称：

  Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.9b06360

文献信息

• Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes
  作者：Harry Adams、Amelia J. Hughes、Michael J. Morris、Sophia I.A. Quenby

  DOI：10.1016/j.tetlet.2014.07.104

  日期：2014.9

  reaction of acetylide anions with carbon disulfide or phenyl isothiocyanate followed by addition of sulfur in the presence of a protonating agent such as a primary amine or alcohol affords 1,2-dithiole-3-thiones or 3-imino-1,2-dithioles in good to excellent yields.

  乙炔根阴离子与二硫化碳或异硫氰酸苯酯的反应，然后在质子化剂（例如伯胺或醇）的存在下添加硫，得到1,2-二硫代-3-硫酮或3-亚氨基-1,2-二硫醇产量高到极好。
• New ways of synthesis of 1,2-dithiole-3-thione
  作者：N. A. Korchevin、N. V. Russavskaya、G. A. Yakimova、E. N. Deryagina

  DOI：10.1007/s11176-005-0095-3

  日期：2004.11

  Two new synthetic approaches to 1,2-dithiole-3-thione are proposed. The title compound is formed by thermolysis of dipropyl polysulfides (n-Pr)2Sx (x = 3–4) and thermal decomposition of polysulfide dendrimers under reduced pressure. The latter reaction may be recommended for utilization of organochlorine waste products in the manufacture of epichlorohydrin, which are used for the synthesis of dendrimers.

  提出了两种新的 1,2-二硫醇-3-硫酮合成方法。标题化合物是通过二丙基多硫化物 (n-Pr)2Sx (x = 3–4) 的热分解和多硫化物树枝状聚合物在减压下的热分解而形成的。后一种反应可推荐用于在环氧氯丙烷的制造中利用有机氯废物，环氧氯丙烷用于合成树枝状聚合物。
• Charbonnel-Jobic, Gaelle; Guemas, Jean-Pierre; Adelaere, Bruno, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 624 - 636
  作者：Charbonnel-Jobic, Gaelle、Guemas, Jean-Pierre、Adelaere, Bruno、Parrain, Jean-Luc、Quintard, Jean-Paul

  DOI：——

  日期：——
• Challenger et al., Journal of the Chemical Society, 1953, p. 292,304
  作者：Challenger et al.

  DOI：——

  日期：——
• Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents
  作者：M. Arbelot、A. Allouche、K. F. Purcell、M. Chanon

  DOI：10.1021/jo00113a010

  日期：1995.4

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.

表征谱图