3,5-二硝基-2-苯基氨基噻吩 | 959-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3,5-二硝基-2-苯基氨基噻吩
• 英文名称: 3,5-dinitro-2-phenylaminothiophene
• 英文别名: 2-Thiophenine, 3,5-dinitro-n-phenyl thiophene, 2-anilino-3,5-dinitro-；3,5-dinitro-N-phenylthiophen-2-amine
• CAS: 959-38-6
• 化学式: C₁₀H₇N₃O₄S
• 分子量: 265.249
• InChiKey: XTHINSIFAJZOSG-UHFFFAOYSA-N

物化性质

• 熔点：
  162-163 °C(Solv: ethanol (64-17-5))
• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

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：
  132
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯胺 以 苯 为溶剂， 以95%的产率得到3,5-二硝基-2-苯基氨基噻吩
  参考文献：
  名称：

  Arnone, Caterina; Consiglio, Giovanni; Spinelli, Domenico, Journal of the Chemical Society. Perkin transactions II, 1990, # 12, p. 2153 - 2156

  摘要：

  DOI：

文献信息

• Aromatic nucleophilic substitution reactions of some 2-L-3-nitro-5-X-thiophenes with piperidine and aniline in methanol. Substituent constants for the thiophene system
  作者：Giovanni Consiglio、Vincenzo Frenna、Caterina Arnone、Elisabetta Mezzina、Domenico Spinelli

  DOI：10.1039/p29940002187

  日期：——

  The rate constants for the reactions of some 2-L-3-nitro-5-X-thiophenes 1–4 with aniline and of compounds (4) with piperidine in methanol have been measured at various temperatures. By using the data obtained in this work as well as previously available data sets, a series of optimized ‘thiophene’σT values has been calculated. The susceptibility constants ρ(L)of the various sets have been analysed

  对于某些2-L-3-硝基-5--X-噻吩的反应速率常数1 - 4与苯胺和化合物（的4用在甲醇中的哌啶）已经在不同温度下进行了测量。通过使用在这项工作中获得的，以及先前可用的数据集的数据，一系列优化“thiophene'σ的Ť值已被计算。在反应性-选择性原理的框架内分析了各种集合的磁化常数ρ（L）。
• 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）
• Nucleophilicities of para‐substituted aniline radical cations in acetonitrile: Kinetic investigation and structure–reactivity relationships
  作者：Ghabi Amira、Souissi Salma、Gabsi Wahiba、Boubaker Taoufik

  DOI：10.1002/kin.21531

  日期：2021.12

  that the nucleophilicity parameters N and E° values of oxidation potential constants are linearly related in a direct relationship with a correlation parameter of R2 = 0.9914. The effect of aniline nucleophilicity on reactivity was examined quantitatively on the basis of kinetic measurements, leading to a nonlinear relationship of log (k20°C) with nucleophilicity parameters (N). It is suggested that

  2-溴-3,5-二硝基噻吩1与各种苯胺2a-f的偶联动力学在 CH 3 CN 中于 20°C 进行了研究。具有吸电子基团（例如，苯胺的导出二阶速率常数2D-F ）被用来确定亲电性参数Ë的噻吩1根据相关等式日志ķ 20℃  = S Ñ（Ë + N )，其中N和 s N是亲核试剂特异性参数。讨论了非线性 Brønsted 和 Hammett 关系，并表明供体苯胺2a-d的反应通过单电子转移机制进行。通过观察到氧化电位常数的亲核性参数N和E ° 值与相关参数R 2  = 0.9914呈线性关系，进一步支持该假设。在动力学测量的基础上定量研究了苯胺亲核性对反应性的影响，导致 log ( k 20°C ) 与亲核性参数 ( N）。这表明可以有效地探索观察到的非线性 Mayr 相关性，以评估四取代苯胺自由基阳离子 XC 6 H 4 NH 2 +• (X = OH, OMe, Me)的亲核性参数N并研究它们的反应模式。另一方面，证实了
• Kinetic Study of the Reactions of Some 5-Nitro-2-(4-nitrophenoxy)-3-X-thiophenes with Aniline and 4-Methoxyaniline in Methanol
  作者：Vincenzo Frenna、Gabriella Macaluso、Giovanni Consiglio、Susanna Guernelli、Domenico Spinelli

  DOI：10.1135/cccc19991877

  日期：——

  The rate constants of the title reactions have been measured at various amine concentrations. The second-order kinetic constant for the amino substitution increases in a hyperbolic way as a function of the nucleophile concentration. The k₃^Am/k_-1 ratio for each catalysed system is not a monotonic function of the X substituent. This result has been rationalized in the framework of the SB-GA (Specific Base-General Acid) mechanism of base catalysis.

  本文研究了在不同胺浓度下的标题反应速率常数。氨基取代的二阶动力学常数随着亲核物浓度的增加而呈双曲线增长。每个催化系统的k3Am/k-1比值不是X取代基的单调函数。这个结果在碱催化的SB-GA（特定碱-一般酸）机制框架内得到了解释。
• p-tert-Butylcalix[8]arene catalysed synthesis of 3,5-dinitrothiophene scaffolds: antiproliferative effect of some representative compounds on selective anticancer cell lines
  作者：Piyali Sarkar、Samares Maiti、Krishnendu Ghosh、Sumita Sengupta (Bandyopadhyay)、Ray J. Butcher、Chhanda Mukhopadhyay

  DOI：10.1016/j.tetlet.2013.12.068

  日期：2014.1

  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.

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