4-(4-氟-苯基)-噻唑-2-基]-苯基-胺 | 1427-09-4

• 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: 4-(4-氟-苯基)-噻唑-2-基]-苯基-胺
• 英文名称: 4-(4-fluorophenyl)-N-phenylthiazol-2-amine
• 英文别名: N-phenyl-4-(4-fluorophenyl)thiazol-2-amine；4-(4-fluorophenyl)-2-phenylaminothiazole；[4-(4-fluoro-phenyl)-thiazol-2-yl]-phenyl-amine；2-Phenylamino-4-<4-fluor-phenyl>-thiazol；4-(4-fluorophenyl)-N-phenyl-1,3-thiazol-2-amine
• CAS: 1427-09-4
• 化学式: C₁₅H₁₁FN₂S
• mdl: MFCD00128407
• 分子量: 270.33
• InChiKey: HXVFUSRCVKYALB-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  424.4±37.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氟-苯基)-噻唑-2-基]-苯基-胺 、 盐酸 、 氨 生成 4-(4-fluorophenyl)-2-imino-3-phenyl-2,3-dihydrothiazole
  参考文献：
  名称：

  BRAMLEY S. E.; DUPPLIN V.; GOBERDHAN D. G. C.; MEAKINS G. D., J. CHEM. SOC. PERKIN TRANS.,(1987) N 3, 639-643

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氟苯乙酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 4.0h， 生成 4-(4-氟-苯基)-噻唑-2-基]-苯基-胺
  参考文献：
  名称：

  [bmim]BF4加速一锅法合成2-氨基噻唑类衍生物

  摘要：

  已经研究了一种用于合成 2-（芳基氨基）噻唑的高效且环保的方案。芳基酮、溴代琥珀酰亚胺和硫脲衍生物的两步三组分反应使用[bmim][BF4]离子液体作为溶剂在一锅中进行，并以良好至优异的收率得到产物。此外，离子液体可重复使用至第 5 次，而反应产率没有显着降低。在温和条件（环境温度和相对较短的反应时间）下，以高产率（78-89%）获得了十三种噻唑，并通过 NMR 数据证实了它们的结构。

  DOI：

  10.2174/1570178620666230207093953

文献信息

• Small Molecule Library Synthesis Using Segmented Flow
  作者：Christina M. Thompson、Jennifer L. Poole、Jeffrey L. Cross、Irini Akritopoulou-Zanze、Stevan W. Djuric

  DOI：10.3390/molecules16119161

  日期：——

  Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper we describe a method that adapts flow chemistry to the synthesis of libraries of compounds using a fluorous immiscible solvent as a spacer between reactions. The methodology was validated in the synthesis of two small heterocycle containing libraries. The reactions were performed on a 0.2 mmol scale, enabling tens of milligrams of material to be generated in a single 200 mL reaction plug. The methodology allowed library synthesis in half the time of conventional microwave synthesis while maintaining similar yields. The ability to perform multiple, potentially unrelated reactions in a single run is ideal for making small quantities of many different compounds quickly and efficiently.

  流动化学作为一种简便、高效且安全的合成技术，已获得广泛认可，适用于多种有机和无机分子的制备，其规模从复杂的大型天然产物到硅纳米颗粒不等。本文介绍了一种利用流动化学合成化合物库的方法，该方法采用氟烃不溶性溶剂作为反应间的间隔物。我们在合成两个含小杂环的化合物库中验证了该方法。反应规模为0.2毫摩尔，单次200毫升反应插件即可生成数十毫克的物质。与传统微波合成相比，该方法在保持相似产率的同时，将化合物库合成时间缩短了一半。能够在单次运行中进行多个潜在不相关的反应，这为快速高效地制备少量多种不同化合物提供了理想条件。
• Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles
  作者：Xiaodong Tang、Zhongzhi Zhu、Chaorong Qi、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.orglett.5b03188

  日期：2016.1.15

  copper-catalyzed coupling of oxime acetates with isothiocyanates. Various 4-substituted and 4,5-disubstituted 2-aminothiazoles were formed smoothly under mild reaction conditions. This process involved copper-catalyzed N–O bond cleavage, activation of vinyl sp2 C–H bonds, and C–S/C–N bond formations. It is noteworthy that the oxime acetates were used not only as a substrate but also as a single oxidant

  通过肟肟铜与异硫氰酸酯的铜催化偶联，开发了2-氨基噻唑的新策略。在温和的反应条件下平稳地形成了各种4-取代的和4,5-二取代的2-氨基噻唑。该过程涉及铜催化的N–O键断裂，乙烯基sp 2 C–H键的活化以及C–S / C–N键的形成。值得注意的是，肟肟不仅用作底物，而且用作单一氧化剂。
• Highly Efficient Heterogeneous Copper-Catalysed Coupling of Oxime Acetates with Isothiocyanates Leading to 2-Aminothiazoles
  作者：Yuxin Tuo、Fang Yao、Yang Liao、Mingzhong Cai

  DOI：10.3184/174751917x14894997017739

  日期：2017.4

  The heterogeneous coupling reaction of oxime acetates with isothiocyanates was achieved at 110 °C in toluene in air in the presence of a bidentate nitrogen-functionalised MCM-41-immobilised copper(I) complex (MCM-41-2N-CuI) with Cs2CO3 as base to afford a variety of 2-aminothiazoles in good yields. The MCM-41-2N-CuI catalyst can be easily recovered by a simple filtration and reused at least eight times

  在二齿氮官能化 MCM-41 固定化铜 (I) 配合物 (MCM-41-2N-CuI) 和 Cs2CO3 存在下，在 110 °C 的甲苯中，在空气中实现了肟乙酸酯与异硫氰酸酯的非均相偶联反应。以良好的收率提供各种 2-氨基噻唑。MCM-41-2N-CuI 催化剂可以通过简单的过滤轻松回收并重复使用至少八次而不会显着降低活性。
• Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature
  作者：Taterao M. Potewar、Sachin A. Ingale、Kumar V. Srinivasan

  DOI：10.1016/j.tet.2008.03.082

  日期：2008.5

  A highly efficient and facile method has been described for the synthesis of substituted 2-aminothiazoles in water without any added catalyst or co-organic solvent. The reaction was carried out at ambient temperature and the products were obtained in excellent isolated yields. The developed protocol is successfully applied for the preparation of an anti-inflammatory drug, fanetizole.

  已经描述了一种在不添加任何催化剂或共有机溶剂的情况下在水中合成取代的2-氨基噻唑的高效且简便的方法。该反应在环境温度下进行，并且产物以优异的分离产率得到。所开发的方案已成功应用于抗炎药Fanetizole的制备。
• Effect of Substituents on the Regioselectivity of the Reaction of α-Tosyloxyketones with Thioureas in Acidic Medium: Access to 2-Aminothiazoles and 2-Imino-2,3-dihydrothiazoles
  作者：Ranjana Aggarwal、Rajiv Kumar、Dionisia Sanz、Rosa M. Claramunt

  DOI：10.1002/jhet.1676

  日期：2014.5

  Regioselective condensation of α‐tosyloxyacetophenones 1 and N‐substituted thioureas 2 in acidic medium to give regioisomers 2‐aminothiazoles I and 2‐imino‐2,3‐dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism, supported by DFT calculations has been proposed to explain the observed regioselectively.

  α-甲苯磺酰氧基苯乙酮1和N-取代的硫脲2在酸性介质中的区域选择性缩合反应产生区域异构体2-氨基噻唑I和2-亚氨基-2,3-二氢噻唑II在很大程度上受到1和2上存在的取代基的影响。已经提出了一种由DFT计算支持的机制来选择性地解释所观察到的区域。