(5Z)-N-(3,4-diphenylthiazol-2(3H)-ylidene)benzenamine

• 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: (5Z)-N-(3,4-diphenylthiazol-2(3H)-ylidene)benzenamine
• 英文别名: (Z)-N-(3,4-diphenylthiazol-2(3H)-ylidene)aniline；N-(3,4-diphenylthiazol-2(3H)-ylidene)phenylamine；3,4-diphenyl-2-phenylimino-3H-thiazole
• 化学式: C₂₁H₁₆N₂S
• 分子量: 328.437
• InChiKey: HAFRCFZWBMTRDZ-DQRAZIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.29
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z)-N-(3,4-diphenylthiazol-2(3H)-ylidene)benzenamine 、 sodium hydrogen selenide 、 硫酸二甲酯 以55%的产率得到
  参考文献：
  名称：

  KOROHODA, M. J., POL. J. CHEM., 1983, 57, N 7-9, 875-880

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙炔 在 碘化铵 、 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (5Z)-N-(3,4-diphenylthiazol-2(3H)-ylidene)benzenamine
  参考文献：
  名称：

  A Base-Free Multicomponent Domino Approach: One-Pot Synthesis of 2-Iminothiazolines via Oxy-Iodination of Arylacetylenes

  摘要：

  A simple and an efficient multicomponent domino protocol is developed for the synthesis of 2-iminothiazolines starting from simple and readily available arylacetylenes, amines, and phenyl isothiocyanates under base-free conditions. The present method involves oxy-iodination of the arylacetylenes with ammonium iodide and hydrogen peroxide, followed by cyclization processes. A number of diversely functionalized 2-iminothiazolines are synthesized in good to excellent yields.

  DOI：

  10.1055/s-0035-1560502

文献信息

• An improved one-pot multicomponent strategy for the preparation of thiazoline, thiazolidinone and thiazolidinol scaffolds
  作者：K. Appalanaidu、Tulshiram Dadmal、N. Jagadeesh Babu、Ravindra M. Kumbhare

  DOI：10.1039/c5ra17278k

  日期：——

  A facile multicomponent synthesis of desirable medicinal scaffolds based on thiazoline, thiazolidinone and thiazolidinol derivatives has been disclosed. The synthesis employs the reaction of a primary amine and carbon disulphide in a microwave, to generate a symmetrical thiourea in situ. The subsequent addition of e.g. 3-bromo-1,1,1-trifluoropropan-2-one affords the desired product, in an efficient

  已经公开了基于噻唑啉，噻唑烷酮和噻唑烷醇衍生物的所需药物支架的容易的多组分合成。该合成利用伯胺和二硫化碳在微波中的反应，原位生成对称的硫脲。随后加入例如3-溴-1,1,1-三氟丙烷-2-酮以有效的一锅法得到所需产物。
• A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues
  作者：Siva Murru、C.B. Singh、Veerababurao Kavala、Bhisma K. Patel

  DOI：10.1016/j.tet.2007.11.076

  日期：2008.2

  3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the pKas of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of

  首次分离出反应中间体，从而进一步了解了噻唑-2-亚胺的形成机理。反应的第一步需要碱性介质，而第二步是酸介导的E1消除反应。通过使用1,1'-（乙烷-1,2-二基）双吡啶鎓溴化吡啶鎓（EDPBT）将羰基化合物与硫脲和1,3-二取代的硫脲缩合，已实现了有效的一锅合成取代的噻唑-2-亚胺。 ）。不对称的1,3-二取代的硫脲会产生带有对称酮的区域选择性产物，该酮主要由p K a决定。s的是硫脲的NH质子，而对称的1,3-二取代的硫脲由于酮的区域选择性溴化作用而产生具有对称羰基化合物的区域选择性产物。该方法已扩展为在较短的反应时间内以高收率获得新型神经退行性药物候选品菲丝菌素-α类似物。该方法简单，通用，可用于不同的1,3-二取代的硫脲以及一系列羰基化合物。
• One-pot multicomponent synthesis of novel thiazol-2-imines <i>via</i> microwave irradiation and their antifungal evaluation
  作者：Saba Kauser Jaweed Shaikh、Ravindra Ramappa Kamble、Shilpa M. Somagond、Atulkumar A. Kamble、Mahadev N. Kumbar

  DOI：10.1080/00397911.2018.1482348

  日期：2018.8.18

  Abstract Microwave-assisted green approach is developed for an efficient synthesis of thiazol-2-imines under catalyst-free conditions. The desired products are formed by one-pot three-component reaction which is an improvised method for Hantzsch thiazole synthesis. The microwave-assisted protocol gives excellent yields with high purity in just 10–15 min. All the synthesized compounds have been screened

  摘要 开发了微波辅助绿色方法，用于在无催化剂条件下有效合成噻唑-2-亚胺。所需产物是通过一锅三组分反应形成的，这是 Hantzsch 噻唑合成的一种简易方法。微波辅助方案可在短短 10-15 分钟内提供高纯度的优异产量。所有合成的化合物都已经过抗真菌活性筛选，一些衍生物对真菌病原体显示出广谱。图形概要
• An efficient synthesis of thiazol-2-imine derivatives via a one-pot, three-component reaction
  作者：Majid M. Heravi、Setareh Moghimi

  DOI：10.1016/j.tetlet.2011.11.017

  日期：2012.1

  A simple and highly efficient one-pot, three-component procedure for the synthesis of thiazol-2-imines, via the reaction of aromatic α-bromoketones, primary amines, and phenyl isothiocyanate in the presence of a catalytic amount of triethylamine, is described.

  描述了一种简单而高效的一锅三组分合成噻唑-2-亚胺的方法，该方法是在催化量的三乙胺存在下，通过芳族α-溴代酮，伯胺和异硫氰酸苯酯的反应进行的。
• Sequential change in one-pot, three-component protocol: A stepping stone in heterocyclic synthesis
  作者：Ranganathan Raja、Dinesh Murugan、Archana Sivasubramaniyan、Jaabil George、Sakthivel Perumal、Ponnuswamy Alagusundaram、Mohan Raj Jayakumar、Murugavel Saminathan

  DOI：10.1080/00397911.2016.1178775

  日期：2016.6.2

  Two different heterocycles, thiazole-2-imines and imidazole-2-thiones, have been conveniently synthesized by just altering the sequential order (1 + 2 + 3 or 1 + 3 + 2) when combining the same components [aryl amine (1), aryl isothiocyanate (2), and phenacyl bromide (3)] in one-pot, three-component protocols. The third possible sequential order of combination (2 + 3 + 1) chemoselectively affords thiazole-2-imine. The finding is a stepping stone in the synthetic applicability of sequential one-pot, three-component protocols.[GRAPHICS].