1-(2,4-二甲基苯基)-3-苯基硫脲 | 13140-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,4-二甲基苯基)-3-苯基硫脲
• 英文名称: N-(2,4-dimethylphenyl)-N’-phenylthiourea
• 英文别名: 1-(2,4-dimethylphenyl)-3-phenylthiourea；N-(2,4-dimethyl-phenyl)-N'-phenyl-thiourea；N-(2,4-Dimethyl-phenyl)-N'-phenyl-thioharnstoff
• CAS: 13140-56-2
• 化学式: C₁₅H₁₆N₂S
• 分子量: 256.371
• InChiKey: ISPHYXKLAGBGOB-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±52.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,4-二甲基苯基)-3-苯基硫脲 在 potassium iodate 、 sodium hydroxide 作用下， 生成 N-(2,4-dimethylphenyl)-N'-phenyl-urea
  参考文献：
  名称：

  DESULFURIZATION OF THIOUREAS BY BROMATE AND IODATE SOLUTIONS

  摘要：

  DOI：

  10.1021/ja01350a023
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 2,4-二甲基苯胺 以 乙腈 为溶剂， 反应 0.17h， 以99%的产率得到1-(2,4-二甲基苯基)-3-苯基硫脲
  参考文献：
  名称：

  A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents

  摘要：

  异硫氰酸酯与胺的机械化学点击偶联反应已被用作模型反应，证明了无溶剂研究实验室的概念适用于小有机分子的合成，该概念消除了化学合成或结构表征中对大量溶剂的使用。虽然通过简单手动研磨反应物可以实现高产率的点击偶联，但使用电动、数字可控的实验室研磨机提供了一种快速、定量且普遍适用的方法，用于合成对称和非对称的芳香或芳香-脂肪族硫脲。与手工研钵合成相比，电动球磨技术（干磨或液体辅助研磨）在合成49种不同的硫脲衍生物中展示了其效率的提升。通过将机械化学产品的粉末X射线衍射数据与剑桥结构数据库（CSD）中的结构信息或通过单晶X射线衍射获得的信息进行比较，表明机械化学合成的硫脲衍生物在化学意义上是纯净的，同时在超分子意义上也可以是纯净的，即在所有结构探索的情况下，产品只包含一种多晶型物。作为我们之前关于无溶剂合成配位聚合物工作的延伸，现在证明了选定的硫脲衍生物的多晶型和化学纯度（后者通过定量反应产率得到证实）能够通过粉末X射线衍射辅助的固态核磁共振光谱直接进行无溶剂的结构表征。

  DOI：

  10.1039/c2gc35799b

文献信息

• Novel Synthesis of 2,4-Dihydro-5-amino[1,2,4]triazol-3-ones from 1,3-Disubstituted Thioureas
  作者：Weike Su、Can Jin、Chuangwei Liu

  DOI：10.1055/s-0028-1087563

  日期：2009.3

  A facile two-step synthesis of 2,4-dihydro-5-amino-[1,2,4]triazol-3-ones is described. Firstly, 1,3-disubstituted thioureas reacted with bis(trichloromethyl) carbonate (BTC) in the presence of a base such as NaHCO3 to form the intermediate 4-(arylimino)-1,3-thiazetidin-2-ones almost quantitatively. Then the intermediates were treated with hydrazine monohydrate to give 2,4-dihydro-5-amino[1,2,4]triazol-3-ones in high yields. In the case of highly sterically hindered thioureas, carbodiimides were unexpectedly obtained in high yields under the same conditions.

  描述了一种简单的两步合成2,4-二氢-5-氨基-[1,2,4]三唑-3-酮的方法。首先，1,3-二取代硫脲在如NaHCO3的碱性环境下与双（三氯甲基）碳酸酯（BTC）反应，几乎定量地形成中间体4-(芳基亚氨基)-1,3-噻唑烷-2-酮。然后，将中间体与单水合肼反应，得到高产率的2,4-二氢-5-氨基[1,2,4]三唑-3-酮。在高度立体位阻的硫脲的情况下，在相同条件下意外地得到高产率的氨基脲。
• Dixon, Journal of the Chemical Society, 1895, vol. 67, p. 558
  作者：Dixon

  DOI：——

  日期：——
• Oxidative desulfurization of disubstituted thioureas using Pb(II) salts and investigation of p<i>K</i>_a-dependent regioselective N-acylation
  作者：Harisadhan Ghosh、Soumya Sarkar、Abdur Rezzak Ali、Bhisma K. Patel

  DOI：10.1080/17415990903295686

  日期：2010.2

  A highly efficient method for the N-acylation of both symmetrical and unsymmetrical thioureas by the use of lead (II) salts and triethylamine has been achieved. The reaction gives regioselective N-acylated product for unsymmetrical thiourea. For unsymmetrical thiuourea, regioselective N-acylation takes place towards the amine having lower pKa. A linear correlation between the pKas of the amines and the regioselective N-acylation is found. Another attractive feature of this transformation is that lead sulfide, which is important to material science, is obtained as a side product (nanocubes of 20nm).
• &lt;p&gt;Enzyme Inhibitory, Antioxidant And Antibacterial Potentials Of Synthetic Symmetrical And Unsymmetrical Thioureas&lt;/p&gt;
  作者：Sumaira Naz、Muhammad Zahoor、Muhammad Naveed Umar、Barkat Ali、Riaz Ullah、Abdelaaty A Shahat、Hafiz Majid Mahmood、Muhammad Umar Khayam Sahibzada

  DOI：10.2147/dddt.s225311

  日期：——

  Background: In this study, 2 symmetrical and 3 unsymmetrical thioureas were synthesized to evaluate their antioxidant, antibacterial, antidiabetic, and anticholinesterase potentials.Methods: The symmetrical thioureas were synthesized in aqueous media in the presence of sunlight, using amines and CS2 as starting material. The unsymmetrical thioureas were synthesized using amines as a nucleophile to attack the phenyl isothiocyanate (electrophile). The structures of synthesized compounds were confirmed through H-1 NMR. The antioxidant potential was determined using DPPH and ABTS assays. The inhibition of glucose-6-phosphatase, alpha amylase, and alpha glucosidase by synthesized compounds was used as an indication of antidiabetic potential. Anticholinesterase potential was determined from the inhibition of acetylcholinesterase and butyrylcholinesterase by the synthesized compounds.Results: The highest inhibition of glucose-6-phosphatase was shown by compound V (03.12 mg of phosphate released). Alpha amylase was most potently inhibited by compound IV with IC50 value of 62 mu g/mL while alpha glucosidase by compound III with IC50 value of 75 mu g/mL. The enzymes, acetylcholinesterase, and butyrylcholinesterase were potently inhibited by compound III with IC50 of 63 mu g/mL and 80 mu g/mL respectively. Against DPPH free radical, compound IV was more potent (IC50 = 64 mu g/mL) while ABTS was more potently scavenged by compound I with IC50 of 66 mu g/mL. The antibacterial spectrum of synthesized compounds was determined against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Agrobacterium tumefaction and Proteus vulgaris). Compound I and compound II showed maximum activity against A. tumefaction with MIC values of 4.02 and 4.04 mu g/mL respectively. Against P. vulgaris, compound V was more active (MIC = 8.94 mu g/mL) while against S. aureus, compound IV was more potent with MIC of 4.03 mu g/mL.Conclusion: From the results, it was concluded that these compounds could be used as antibacterial, antioxidant, and antidiabetic agents. However, further in vivo studies are needed to determine the toxicological effect of these compounds in living bodies. The compounds also have potential to treat neurodegenerative diseases.
• Levi, 1924, p. 402
  作者：Levi

  DOI：——

  日期：——

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