4-(4-fluorophenyl)-2-phenylthiazole | 329079-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-fluorophenyl)-2-phenylthiazole
• 英文别名: 4-(4-Fluorophenyl)-2-phenyl-1,3-thiazole
• CAS: 329079-72-3
• 化学式: C₁₅H₁₀FNS
• mdl: MFCD00954926
• 分子量: 255.316
• InChiKey: AKLPVIMTYUAFOD-UHFFFAOYSA-N

物化性质

• 沸点：
  408.2±37.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

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 、 4-(4-fluorophenyl)-2-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83%的产率得到4-(4-fluorophenyl)-2-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-氟苯乙烯 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4-(4-fluorophenyl)-2-phenylthiazole
  参考文献：
  名称：

  One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS

  摘要：

  将商业可获得的苯乙烯与NBS在水中加热，然后与2-氨基吡啶和硫代酰胺反应，在一锅法中得到重要的杂环骨架。

  DOI：

  10.1039/c5gc02771c

文献信息

• Syntheses of biodynamic heterocycles: baker’s yeast-assisted cyclocondensations of organic nucleophiles and phenacyl chlorides
  作者：Lalit D. Khillare、Umesh R. Pratap、Manisha R. Bhosle、Sambhaji T. Dhumal、Mahendra B. Bhalerao、Ramrao A. Mane

  DOI：10.1007/s11164-017-2880-0

  日期：2017.8

  pyridin-2-amine (2f) at room temperature in presence of baker’s yeast to give fused heterocycles 6-(4-substituted phenyl)-2-phenylimidazo[2,1-b][1,3,4]thiadiazoles (5a–f), 2-(4-substituted phenyl)quinoxalines (6a–f), 6-(4-substituted phenyl)-3-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (7a–f), and 2-(4-substituted phenyl)H-imidazo[1,2-a]pyridines (8a–f), respectively. The experimental conditions for these

  在室温下，在乙腈中作为全细胞酶源的面包酵母（Saccharomyces cerevisiae）存在下，将取代的苯甲酰氯（1a – f）与亲核试剂硫脲（2a）和硫代苯甲酰胺（2b）进行环缩合反应，得到4-（4-取代的苯基） ）噻唑-2-胺（3a – f）和4-（取代的苯基）-2-苯基噻唑（4a – f）。此外，取代的苯甲酰氯还与亲核试剂2-氨基-1,3,4-噻二唑（2c），邻苯二胺（2d），1-氨基-2-巯基-5-苯基三唑（2e）和吡啶-2-胺（2f），在面包酵母的存在下于室温下产生稠合的杂环6-（4-取代的苯基）-2-苯基咪唑并[2,1- b ] [1,3,4]噻二唑（5a – f），2-（4-取代的苯基）喹喔啉（6a – f），6-（4-取代的苯基）-3-苯基-7 H- [1,2,4]三唑[3,4] - b ] [1,3,4]噻二嗪（7A - ˚F），和2-（4-取代苯基）ħ -咪唑并[1
• 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。
• One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
  作者：Takahiro Yamamoto、Hideo Togo

  DOI：10.1002/ejoc.201800730

  日期：2018.8.15

  Primary aromatic amides, 4‐arylthiazoles, and 4‐arylimidazoles were smoothly obtained from arenes in good yield in one pot via aryl α‐bromoacetylarenes, which were obtained by reacting simple arenes with α‐bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidine under transition‐metal‐free conditions.

  一锅中通过芳基α-溴乙酰芳烃轻松从芳烃中以高收率顺利获得伯芳族酰胺，4-芳基噻唑和4-芳基咪唑，这些芳烃是通过将简单的芳烃与α-溴乙酰氯和AlCl 3反应，然后与分子碘和水溶液 在无过渡金属的条件下，NH 3，硫酰胺或am。
• Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles
  作者：Gaofeng Yin、Xiaodong Wang、Yuqing Wang、Tao Shi、Yaofu Zeng、Yuying Wang、Xue Peng、Zhen Wang

  DOI：10.1039/d2ob01939f

  日期：——

  Azlactones and thiazoles are common structural motifs and possess diverse applications. A new method for the efficient and straightforward syntheses of 2,4-disubstituted thiazoles from azlactones has been developed. The reaction proceeded via deoxygenation of azlactones by Lawesson's reagent without metal or external additives. A variety of 2,4-disubstituted thiazoles were synthesized with up to 92%

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。
• 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。