N-(4-Nitrophenyl)-thiocarbamidsaeure-O-ethylester | 13806-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-Nitrophenyl)-thiocarbamidsaeure-O-ethylester
• 英文别名: (E)-O-Ethyl N-(4-nitrophenyl)thiocarbamate；O-ethyl N-(4-nitrophenyl)carbamothioate
• CAS: 13806-75-2
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: CDBFMIIDUWJTTF-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  332.2±44.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-Nitrophenyl)-thiocarbamidsaeure-O-ethylester 在 sodium hydroxide 作用下， 生成 N-(4-硝基苯基)氨基甲酸乙酯
  参考文献：
  名称：

  Jacobson; Klein, Chemische Berichte, 1893, vol. 26, p. 2365

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 1,3-双(4-硝基苯基)硫脲 反应 1.5h， 以100%的产率得到N-(4-Nitrophenyl)-thiocarbamidsaeure-O-ethylester
  参考文献：
  名称：

  Derume, Anita; Egg, Helmut; Koenig, Roman, Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 327 - 333

  摘要：

  DOI：

文献信息

• Copper/Nickel-Catalyzed Selective C-S/S-S Bond Formation Starting from <i>O</i> -Alkyl Phenylcarbamothioates
  作者：Kang Peng、Ming-Yuan Gao、Yu-Yan Yi、Jia Guo、Zhi-Bing Dong

  DOI：10.1002/ejoc.201901884

  日期：2020.3.22

  An effective method is described to construct C–S/S–S bond starting from O‐alkyl phenylcarbamothioates, giving diverse O‐alkyl S‐phenyl phenylcarbonimidothioates or isothiourea disulfides, by using Cu2O as catalyst in water (without phase‐transfer catalyst) or NiBr2 catalyst at room temperature, respectively, in transformations featuring easy control, environmental friendliness, and good to excellent

  描述了一种有效的方法，该方法通过使用Cu 2 O作为催化剂在水中（不使用相转移催化剂），从O-烷基苯基氨基甲硫代酸酯开始构建C-S / S-S键，得到各种O-烷基S-苯基苯基碳亚氨基硫代酸酯或异硫脲二硫化物。）或NiBr 2催化剂分别在室温下进行转化，具有易于控制，对环境友好的特点以及良好或优异的收率。
• Syntheses of N-alkyl, N,N-dialkyl, and N-(4-substituted phenyl) O-ethyl thioncarbamates: a kinetic study
  作者：Milutin M. Milosavljević、Aleksandar D. Marinković、Vlada B. Veljković、Dragan D. Milenković

  DOI：10.1007/s00706-011-0596-1

  日期：2012.1

  AbstractThe kinetics of the syntheses of N-alkyl, N,N-dialkyl, and N-(4-substituted phenyl) O-ethyl thioncarbamates from sodium ethyl xanthogenacetate, ten alkylamines, and eight substituted anilines were studied at 25, 30, 35, and 40 °C. The reactions were found to follow second-order kinetics. The kinetic (Arrhenius) parameters, such as the activation energy and the frequency factor, as well as the

  摘要N-烷基，N，N-二烷基和N-（4-取代的苯基）O的合成动力学在25、30、35和40°C下研究了由黄原酸乙酯钠，十个烷基胺和八个取代的苯胺生成的亚乙基乙基氨基甲酸酯。发现反应遵循二级动力学。由二阶速率计算出动力学（Arrhenius）参数，例如活化能和频率因子，以及Eyring参数，例如标准熵，标准吉布斯能量和标准活化焓。常数。根据提出的动力学研究和使用MOPAC PM6半经验方法对反应机理进行了优化，推测了反应机理。 图形概要
• Synthesis of Unsymmetric Thiosulfonates Starting from N-Substituted <i>O</i>-Thiocarbamates: Easy Access to the S–SO₂ Bond
  作者：Cheng-Li Yang、Xue-Jie Gao、Xin-Yi Jiang、Zhen Shi、Er-Jun Hao、Zhi-Bing Dong

  DOI：10.1021/acs.joc.2c01301

  日期：2022.9.2

  Using phenyliodine diacetate as an oxidant and nickel acetate as a promoter, a wide range of unsymmetric thiosulfonates could be furnished easily in moderate to excellent yields starting from N-substituted O-thiocarbamates and sodium sulfinates. This protocol features mild conditions, short reaction times, and high atomic utilization, which can provide an alternative method for the synthesis of unsymmetric

  使用苯碘二乙酸盐作为氧化剂和乙酸镍作为促进剂，可以从 N-取代的O-硫代氨基甲酸盐和亚磺酸钠开始以中等至优异的产率轻松提供各种不对称硫代磺酸盐。该协议具有条件温和、反应时间短、原子利用率高等特点，可为不对称硫代磺酸盐的合成提供一种替代方法。此外，该反应可按克级放大，显示出潜在的工业应用价值。
• Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions
  作者：Wen-Jie Liu、Zhi-Chao Hu、Yu-Xi Wu、Shi-Hao Deng、Zhi-Lin Ren、Zhi-Bing Dong

  DOI：10.1021/acs.joc.3c02940

  日期：2024.3.15

  A method for the selective construction of S–N/C(sp2)-S bonds using N-substituted O-thiocarbamates and indoles as substrates is reported. This protocol features good atom utilization, mild conditions, short reaction time, and wide substrate scope, which can provide a convenient path for the functionalization of indoles. In addition, the reaction could be scaled up on gram scale, showing potential application

  报道了一种使用N-取代的O-硫代氨基甲酸酯和吲哚作为底物选择性构建S-N/C(sp 2 )-S键的方法。该方案具有原子利用率好、条件温和、反应时间短、底物范围广的特点，为吲哚的功能化提供了便捷的途径。此外，该反应可放大至克级，在工业合成中显示出潜在的应用价值。
• Kinetics of the mercury(II) ion-promoted desulfurisation of thiocarbamates in aqueous solution
  作者：Derek P. N. Satchell、Rosemary S. Satchell、Wasfy N. Wassef

  DOI：10.1039/p29920001091

  日期：——

  In a 1% dioxane-water solvent in the presence of Hg2+ ions thiocarbamates p-RC6H4NHC(S)OEt (R = MeO, Me, H, F) rapidly form complexes of 2 thiocarbamate: 1 Hg2+ stoichiometry. In the presence of an excess of Hg2+ ions partial conversion to the 2:2-complexes probably occurs which decompose to the corresponding carbamates (p-RCH4NHCO2Et) and HgS. With R = NO2 the 2:2 complex is dominant even at low Hg2+ ion concentrations, and desulfurisation is then independent of [Hg2+] . Electron-withdrawal by R favours the 2:2 complex but decreases its rate of decomposition to products. The effects of changes in the hydrogen ion concentration suggest that ionisation of N-bound protons in the complexes favours reaction. A mechanism is suggested. The kinetic behaviour is somewhat similar to that found previously for thiobenzamides, but the new results suggest the mechanism previously proposed may need revision.