3,5-dinitro-2-phenylsulfanylthiophene | 21817-36-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,5-dinitro-2-phenylsulfanylthiophene
• 英文别名: 3,5-dinitro-2-phenylsulfanyl-thiophene；3,5-Dinitro-2-phenylmercapto-thiophen
• CAS: 21817-36-7
• 化学式: C₁₀H₆N₂O₄S₂
• 分子量: 282.301
• InChiKey: ZFBPLJVKXTYKDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-bromo-3,5-dinitro-thiophene 、 苯硫酚 在 4-叔丁基杯[8]芳烃 作用下， 以 水 为溶剂， 以85%的产率得到3,5-dinitro-2-phenylsulfanylthiophene
  参考文献：
  名称：

  p-tert-Butylcalix[8]arene catalysed synthesis of 3,5-dinitrothiophene scaffolds: antiproliferative effect of some representative compounds on selective anticancer cell lines

  摘要：

  A new efficient protocol for the synthesis of 3,5-dinitrothiophene scaffolds was developed by using simple p-tert-butylcalix[8]arene in aqueous medium. Biological activities of some representative compounds were also studied to inhibit the cell growth on selective anticancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.068

文献信息

• Secondary steric effects in SNAr of thiophenes: a coordinate kinetic, thermodynamic, UV–VIS, crystallographic and ab initio study
  作者：Giovanni Consiglio、Vincenzo Frenna、Angelo Mugnoli、Renato Noto、Marcella Pani、Domenico Spinelli

  DOI：10.1039/a604516b

  日期：——

  The reactivity of some dinitro-benzene and -thiophene derivatives with piperidine and sodium benzenethiolate has been examined giving evidence that benzenes show large and thiophenes show small kinetic secondary steric effects, respectively. The acid dissociation reaction and the UV–VIS spectra of some nitrothiophenamines have also been studied. The crystal structure and the absolute conformation of 2-iodo-3,5-dinitrothiophene and of 2-iodo-4-methyl-3,5-dinitrothiophene have been determined. For different conformations of the analogous chlorodinitro derivatives in the thiophene and benzene series, ab initio energy calculations have been performed. The results collected show that steric strain among adjacent groups affects the benzene and thiophene compounds and the kinetic, thermodynamic and spectroscopic properties of the molecules examined differently. Differences in geometry of the two aromatic rings and then in rotation of nitro groups with respect to the rings themselves as well as differences along reaction coordinates (essentially depending on hybridation changes) are used to explain the above data.

  一些二硝基苯和二硫吡啶衍生物与哌啶和苯硫醇钠的反应性已被研究，结果表明苯类化合物显示出较大的动力学次级空间效应，而噻吩类化合物则显示出较小的动力学次级空间效应。还研究了一些硝基噻吡啶胺的酸解离反应及其紫外-可见光谱。已确定了2-碘-3,5-二硝基噻吡啶和2-碘-4-甲基-3,5-二硝基噻吡啶的晶体结构与绝对构象。对于硫代吡啶和苯系列中类似氯代二硝基衍生物的不同构象，进行了从头算能量计算。收集的结果表明，相邻基团之间的立体应变对苯和噻吡啶化合物的影响，以及所研究分子的动力学、热力学和光谱特性不同。两种芳香环的几何结构差异，以及相对于环本身的硝基旋转差异，以及沿反应坐标的差异（主要依赖于杂化变化）被用来解释上述数据。
• Studies on the biological activity of some nitrothiophenes
  作者：John O. Morley、Thomas P. Matthews

  DOI：10.1039/b514441h

  日期：——

  inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5-dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and

  已经通过评估抑制大肠杆菌，黄体分枝杆菌和黑曲霉的生长所需的最小抑菌浓度，评估了十九种取代噻吩的生物活性（3）。该系列显示出广泛的活性，其中2-氯-3,5-二硝基噻吩（3a）或2-溴-3,5-二硝基噻吩（3c）对三种生物均显示出最高的活性，而该系列中最简单的化合物，2-硝基噻吩（3s）在每种情况下均显示最小的活性。人们认为3a和3c的作用方式涉及细胞内硫醇在杂环2位上的亲核攻击，导致卤素置换，但其他活性衍生物（例如2）
• Noto, Renato; Frenna, Vincenzo; Consiglio, Giovanni, Journal of Chemical Research, Miniprint, 1991, # 10, p. 2701 - 2710
  作者：Noto, Renato、Frenna, Vincenzo、Consiglio, Giovanni、Spinelli, Domenico

  DOI：——

  日期：——