2-(4-fluorophenyl)-4-phenylthiazole | 1095792-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-4-phenylthiazole
• 英文别名: 2-(4-Fluorophenyl)-4-phenyl-1,3-thiazole
• CAS: 1095792-53-2
• 化学式: C₁₅H₁₀FNS
• mdl: MFCD12302408
• 分子量: 255.316
• InChiKey: GQWINXMZMDBBRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴吡啶 、 2-(4-fluorophenyl)-4-phenylthiazole 在 palladium diacetate 、 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.17h， 以73%的产率得到2-(4-fluorophenyl)-4-phenyl-5-(pyridin-3-yl)thiazole
  参考文献：
  名称：

  Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating

  摘要：

  Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCI additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.053
• 作为产物：
  描述：

  (4-fluorophenyl)(morpholino)methane thione 、 2-溴苯乙酮 在 四乙基碘化铵 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以84%的产率得到2-(4-fluorophenyl)-4-phenylthiazole
  参考文献：
  名称：

  叔硫酰胺一步法三组分无溶剂合成噻唑

  摘要：

  摘要已经开发了一种新颖的一锅三组分反应，用于在无溶剂条件下构建噻唑衍生物。因此，将叔硫酰胺，α-卤代酮和NH 4 OAc一起研磨，并使其在110°C和/或微波辐射下热反应，以非常好的收率生产相应的噻唑衍生物。 图形概要

  DOI：

  10.1007/s13738-016-0873-3

文献信息

• Brønsted acid-promoted thiazole synthesis under metal-free conditions using sulfur powder as the sulfur source
  作者：Penghui Ni、Jing Tan、Rong Li、Huawen Huang、Feng Zhang、Guo-Jun Deng

  DOI：10.1039/c9ra09656f

  日期：——

  acid-promoted sulfuration/annulation reaction for the one-pot synthesis of bis-substituted thiazoles from benzylamines, acetophenones, and sulfur powder has been developed. One C–N bond and multi C–S bonds were selectively formed in one pot. The choice of the Brønsted acid was the key to the high efficiency of this transformation under metal-free conditions.

  已经开发了一种由苯甲胺、苯乙酮和硫粉一锅合成双取代噻唑的布朗斯台德酸促进的硫化/环化反应。一个 C-N 键和多个 C-S 键在一锅中选择性地形成。布朗斯台德酸的选择是在无金属条件下实现高效转化的关键。
• Synthesis of 2,4-diarylthiazoles throuth palladium-catalyzed cyclization of sulfoxonium ylides and benzothioamide
  作者：Yi-Xuan Lu、Liang-Wei Zhu、Ting-kang Lv、Bao-Hua Chen

  DOI：10.1016/j.tetlet.2022.154051

  日期：2022.8

  In this paper, the [3 + 2] cycloaddition reaction of thiobenzoyl group derivatives with sulfoxonium ylide was studied, which can directly synthesize 2,4-diarylthiazoles with different structures. Compared with the traditional reaction of producing thiazole, using palladium catalysts is able to make the reaction milder and lower in cost. Thus, a group of 2,4-diarylthiazoles can be easily synthesized

  本文研究了硫代苯甲酰基衍生物与硫鎓叶立德的[3+2]环加成反应，可直接合成不同结构的2,4-二芳基噻唑。与传统生产噻唑的反应相比，使用钯催化剂可以使反应更温和，成本更低。因此，以这种方式可以容易地以中等至高产率合成一组2,4-二芳基噻唑。
• 10.1039/d4ra03290j
  作者：Mahaur, Priya、Rajput, Khushbu、Singh, Vishal、Srivastava, Vandana、Singh, Sundaram

  DOI：10.1039/d4ra03290j

  日期：——

  The lipase-catalyzed, ultrasound-assisted synthesis presented in this study represents a greener and more sustainable alternative to traditional synthetic pathways for these important compounds, offering promising potential for applications in medicinal chemistry and drug development. This approach holds the promise of advancing the field of thiazole synthesis, contributing to more sustainable and efficient

  本研究探索了一种有效合成 2,4-二取代噻唑衍生物的创新方法，这是一类具有多种生物学和药物意义的化合物。这项研究表明脂肪酶是一种高效且环境友好的噻唑合成催化剂。在温和的条件下，芳基乙烯酮、KBrO3 和硫代酰胺的缩合是通过使用超声波能量来辅助的。此外，我们利用超声波照射的力量来加速反应，减少反应时间并提高产品产量。本研究中提出的脂肪酶催化、超声辅助合成代表了这些重要化合物传统合成途径的更环保、更可持续的替代方案，为药物化学和药物开发中的应用提供了广阔的前景。这种方法有望推动噻唑合成领域的发展，为更可持续、更高效的化学工艺做出贡献。
• Visible-light-induced C–S bond formation in the synthesis of 2,4-disubstituted thiazoles through cascade difunctionalization of acetophenone: a greener approach
  作者：Khushbu Rajput、Vishal Singh、Priya Mahaur、Sundaram Singh、Vandana Srivastava

  DOI：10.1039/d4ob00096j

  日期：2024.4.3

  A novel approach for the synthesis of 2,4-disubstituted thiazoles from methyl aryl ketones, N-bromo-succinimide (NBS), and thioamide in water as a green reaction medium through visible-light irradiation is reported.
• Synthesis of trisubstituted thiazoles by ligand-free palladium-catalyzed direct 5-arylation of 2,4-disubstituted thiazoles under conventional and microwave-assisted heating
  作者：Su Kang Kim、Ji-Hyun Kim、Young Chul Park、Jae Won Kim、Eul Kgun Yum

  DOI：10.1016/j.tet.2013.10.053

  日期：2013.12

  Trisubstituted thiazoles were synthesized with excellent yields using ligand-free, palladium-catalyzed, direct 5-arylation of 2,4-disubstituted thiazole and conventional or microwave-assisted heating. The palladium-catalyzed reaction yields were significantly influenced by LiCI additive, solvent, and heating method. The reaction times were reduced dramatically by employing microwave radiation instead of conventional heating. The synthetic methods can be applied to diverse 2,4,5-trisubstituted thiazoles by varying the aryl bromide and disubstituted thiazole reactants. (C) 2013 Elsevier Ltd. All rights reserved.