N-(4-甲基苯基)-5-苯基-1,3,4-噻二唑-2-胺 | 63314-61-4

• 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: N-(4-甲基苯基)-5-苯基-1,3,4-噻二唑-2-胺
• 英文名称: 5-phenyl-N-(p-tolyl)-1,3,4-thiadiazol-2-amine
• 英文别名: N-(4-methylphenyl)-5-phenyl-1,3,4-thiadiazol-2-amine
• CAS: 63314-61-4
• 化学式: C₁₅H₁₃N₃S
• 分子量: 267.354
• InChiKey: ZGLMLPMDTBFJBA-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  430.7±38.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酸苯酯 在 硫酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 N-(4-甲基苯基)-5-苯基-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

  摘要：

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

  DOI：

  10.1021/jm0495632

文献信息

• Efficient synthesis of 1,3,4-thiadiazoles using hydrogen bond donor (thio)urea derivatives as organocatalysts
  作者：Shahnaz Rostamizadeh、Reza Aryan、Hamid Reza Ghaieni、Ali Mohammad Amani

  DOI：10.1002/jhet.367

  日期：——

  A simple and efficient procedure for the synthesis of 1,3,4‐thiadiazoles has been achieved using thiourea as organocatalyst. In this study, the steric and electronic effects using structurally different derivatives of urea and thiourea in different solvents were evaluated. The best yields and the rate of the reactions were obtained using 30 mol % of thiourea as catalyst in acetonitrile at room temperature

  使用硫脲作为有机催化剂，已经实现了一种简单而有效的合成1,3,4-噻二唑的方法。在这项研究中，评估了在不同溶剂中使用结构不同的脲和硫脲衍生物的空间和电子效应。在室温下，使用30mol％的硫脲作为催化剂在乙腈中获得最佳的产率和反应速率。产物的分子结构由1 H和13 C NMR光谱数据确定。J.杂环化​​学。（2010）。
• Synthesis of 2-amino-substituted-1,3,4-thiadiazoles via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated intramolecular C–S bond formation in thiosemicarbazones
  作者：Sarangthem Joychandra Singh、Suresh Rajamanickam、Anupal Gogoi、Bhisma K. Patel

  DOI：10.1016/j.tetlet.2016.01.083

  日期：2016.3

  An effective oxidative intramolecular cyclization (C–S bond formation) of thiosemicarbazones using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has been developed to afford a diverse array of 2-amino-substituted-1,3,4-thiadiazoles. The attractive features of this protocol are operational simplicity, obviates the need of expensive transition-metal catalysts and broad substrate scope.

  已开发出使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）的硫半脲的有效氧化分子内环化（CS键形成），以提供各种2-氨基取代的- 1,3,4-噻二唑。该协议的吸引人的特点是操作简单，无需昂贵的过渡金属催化剂和广泛的底物范围。
• Thiadiazole derivatives as New Class of β-glucuronidase inhibitors
  作者：Uzma Salar、Muhammad Taha、Nor Hadiani Ismail、Khalid Mohammed Khan、Syahrul Imran、Shahnaz Perveen、Abdul Wadood、Muhammad Riaz

  DOI：10.1016/j.bmc.2016.03.020

  日期：2016.4

  Thiadiazole derivatives 1–24 were synthesized via a single step reaction and screened for in vitro β-glucuronidase inhibitory activity. All the synthetic compounds displayed good inhibitory activity in the range of IC50 = 2.16 ± 0.01–58.06 ± 1.60 μM as compare to standard d-saccharic acid 1,4-lactone (IC50 = 48.4 ± 1.25 μM). Molecular docking study was conducted in order to establish the structure–activity

  噻二唑衍生物1 – 24通过一步反应合成，并筛选了体外β-葡萄糖醛酸苷酶抑制活性。 与标准d-蔗糖酸1,4-内酯相比，所有合成化合物在IC 50 = 2.16±0.01–58.06±1.60μM范围内均表现出良好的抑制活性（IC 50  = 48.4± 1.25μM ）。为了建立结构-活性关系（SAR），进行了分子对接研究，该关系表明噻二唑以及两个芳基部分（芳基和N-芳基）都具有抑制作用。所有合成化合物均通过1 H光谱技术进行表征，13 C NMR和EIMS。
• An efficient one-pot procedure for the preparation of 1,3,4-thiadiazoles in ionic liquid [bmim]BF4 as dual solvent and catalyst
  作者：Shahnaz Rostamizadeh、Reza Aryan、Hamid R. Ghaieni、Ali M. Amani

  DOI：10.1002/hc.20432

  日期：2008.4

  The one-pot three component condensation of hydrazine hydrate with substituted phenylisothiocyanates followed by the addition of substituted benzaldehydes in the presence of ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) and in the absence of any other catalyst under mild condition afforded 1,3,4-thiadiazoles in excellent yields. The reaction workup is simple, and the ionic liquid

  在离子液体 1-丁基-3-甲基咪唑鎓四氟硼酸盐 ([bmim]BF4) 存在下，在没有任何其他催化剂的情况下，水合肼与取代的异硫氰酸苯酯的一锅三组分缩合，然后加入取代的苯甲醛条件下以极好的收率提供了 1,3,4-噻二唑。反应后处理简单，离子液体很容易从反应中回收再利用。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:320–324, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20432
• Chemodivergent Photocatalyzed Heterocyclization of Hydrazones and Isothiocyanates for the Selectivity Synthesis of 2-Amino-1,3,4-thiadiazoles and 1,2,4-Triazole-3-thiones
  作者：Qing-Hu Teng、Feng-Lai Lu、Kai Wang、Li-Ya Zhou、Dian-Peng Li

  DOI：10.1021/acs.joc.3c00320

  日期：2023.6.2

  A photocatalytic chemodivergent reaction for the selectivity formation of C–S and C–N bonds in a controlled manner was proposed. The reaction medium, either neutral or acidic, is critical to dictate the formation of 2-amino-1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones from isothiocyanates and hydrazones. This is a practical protocol to achieve the chemoselectivity under mild and metal-free conditions

  提出了一种以受控方式选择性形成 C-S 和 C-N 键的光催化化学发散反应。中性或酸性反应介质对于决定从异硫氰酸酯和腙形成 2-氨基-1,3,4-噻二唑和 1,2,4-三唑-3-硫酮至关重要。这是在温和和无金属条件下实现化学选择性的实用方案。