2-(4-fluorophenyl)-3-phenylthiazolidin-4-one

• 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: 2-(4-fluorophenyl)-3-phenylthiazolidin-4-one
• 英文别名: 2-(4-Fluorophenyl)-3-phenyl-1,3-thiazolidin-4-one
• 化学式: C₁₅H₁₂FNOS
• 分子量: 273.331
• InChiKey: JAOJXAPKRUBUGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-氟苯亚甲基)苯胺 、 巯基乙酸 在 copper(ll) sulfate pentahydrate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到2-(4-fluorophenyl)-3-phenylthiazolidin-4-one
  参考文献：
  名称：

  巯基乙酸的环缩合反应在介孔MCM-41负载的席夫碱和CuSO4·5H2O的高区域选择性催化合成4-噻唑烷酮衍生物中的催化研究

  摘要：

  MCM-41介孔负载的席夫碱和CuSO4·5H2O在巯基乙酸与亚胺（或醛和胺）的环缩合反应中显示出高催化活性，从而提供了重要的噻唑烷酮衍生物。涉及二组分或三组分的催化反应以高收率（高达98％和99％）提供了所需的产物。此外，该催化剂在可回收性方面效果很好，经过六次回收后，产品的收率分别为85％和83％。

  DOI：

  10.1016/j.cclet.2015.10.029

文献信息

• Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports
  作者：Dinesh Kumar、Mukesh Sonawane、Brahmam Pujala、Varun K. Jain、Srikant Bhagat、Asit K. Chakraborti

  DOI：10.1039/c3gc41218k

  日期：——

  The catalytic potential of various protic acids has been assessed for the one pot tandem condensation–cyclisation reaction involving an aldehyde, an amine, and thioglycolic acid to form 2,3-disubstituted thiazolidin-4-ones. The catalytic potential of the various protic acids that follows the order TfOH > HClO4 > H2SO4 ∼ p-TsOH > MsOH ∼ HBF4 > TFA ∼ AcOH is improved significantly by adsorption on solid supports, in particular using silica gel (230–400 mesh size), with the resulting relative catalytic potential following the order HClO4–SiO2 > TfOH–SiO2 ≫ H2SO4–SiO2 > p-TsOH–SiO2 > MsOH–SiO2 ∼ HBF4–SiO2 > TFA–SiO2 ∼ HOAc–SiO2. The better catalytic potential of HClO4–SiO2 as compared to that of Tf–SiO2, although TfOH is a stronger protic acid than HClO4, can be rationalised through a transition state model depicting the interaction of the individual protic acid with SiO2. The catalytic efficiency of HClO4 adsorbed on various solid supports was in the order HClO4–SiO2 ≫ HClO4–K10 > HClO4–KSF > HClO4–TiO2 ∼ HClO4–Al2O3. The catalytic system HClO4–SiO2 is compatible with different variations of aldehydes (aryl/heteroaryl/alkyl/cycloalkyl) and the amines (aryl/heteroaryl/arylalkyl/alkyl/cycloalkyl) affording the desired 2,3-disubstituted thiazolidin-4-ones in 70–87% yields (43 examples). The electronic and the steric factors associated with the aldehydes and the amines provide a handle for selective thiazolidinone formation and were found to be dependent on the extent of imine formation. No significant amount of thiazolidinone formation took place during the reaction of the preformed amide (synthesised from the amine and thioglycolic acid) with benzaldehyde suggesting that the reaction proceeds through the initial reversible imine formation followed by cyclocondensation of the preformed imine with thioglycolic acid, the reversible imine formation being the determining step to control selectivity of thiazolidinone formation in competitive environments. The feasibility of a large scale reaction and catalyst recycling/reuse is demonstrated.

  已对各种质子酸的催化潜能进行了评估，这些质子酸用于涉及醛、胺和巯基乙酸的一锅法串联缩合-环化反应，以形成2,3-二取代的噻唑烷-4-酮。通过吸附在固体载体上，特别是使用硅胶（230-400目大小），可以显著提高各种质子酸的催化潜能，这些质子酸的催化潜能顺序为：TfOH > HClO4 > H2SO4 ∼ p-TsOH > MsOH ∼ HBF4 > TFA ∼ AcOH。所得相对催化潜能的顺序为：HClO4–SiO2 > TfOH–SiO2 ≫ H2SO4–SiO2 > p-TsOH–SiO2 > MsOH–SiO2 ∼ HBF4–SiO2 > TFA–SiO2 ∼ HOAc–SiO2。与Tf–SiO2相比，HClO4–SiO2具有更好的催化潜能，尽管TfOH是一种比HClO4更强的质子酸，这可以通过描述单个质子酸与SiO2相互作用的过渡态模型来合理化。HClO4吸附在各种固体载体上的催化效率顺序为：HClO4–SiO2 ≫ HClO4–K10 > HClO4–KSF > HClO4–TiO2 ∼ HClO4–Al2O3。催化系统HClO4–SiO2与不同变体的醛（芳基/杂芳基/烷基/环烷基）和胺（芳基/杂芳基/芳基烷基/烷基/环烷基）兼容，以70-87%的产率（43个例子）提供所需的2,3-二取代噻唑烷-4-酮。与醛和胺相关的电子和空间因素为选择性噻唑烷酮的形成提供了依据，并发现它们依赖于亚胺形成的程度。在预形成的酰胺（由胺和巯基乙酸合成）与苯甲醛的反应中，没有发生显著量的噻唑烷酮形成，这表明反应通过初始的可逆亚胺形成，然后是预形成的亚胺与巯基乙酸的环化缩合，可逆的亚胺形成是控制竞争环境中的噻唑烷酮形成选择性的决定步骤。大规模反应的可行性以及催化剂的回收/再利用得到了证明。
• Facile synthesis of 1,3-thiazolidin-4-ones as antitubercular agents
  作者：Dnyaneshwar D. Subhedar、Mubarak H. Shaikh、Manisha A. Arkile、Amar Yeware、Dhiman Sarkar、Bapurao B. Shingate

  DOI：10.1016/j.bmcl.2016.02.056

  日期：2016.4

  We have developed, highly efficient, one-pot, solvent-free, [Et3NH][HSO4] catalyzed multicomponent reaction protocol for the synthesis of 1,3-thiazolidin-4-ones in excellent yields. For the first time, the 1,3-thiazolidin-4-ones were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis dormant MTB H37Ra and Mycobacterium bovis BCG strains. Among the synthesized

  我们已经开发出了一种高效，一锅，无溶剂，[Et 3 NH] [HSO 4 ]催化的多组分反应方案，用于以优异的产率合成1,3-噻唑烷酮-4-酮。首次在体外评估了1,3-噻唑烷酮-4-酮对休眠的结核分枝杆菌MTB H37Ra和牛分枝杆菌BCG菌株的抗分枝杆菌活性。在合成的碱性1,3-噻唑烷酮-4-酮中，尤其是化合物4c，4d，4e，4f，4h，4i和4j 显示出有希望的抗结核活性，并且对细胞系MCF-7，A549和HCT-116没有明显的细胞毒性。
• β-Cyclodextrin-SO3H-catalyzed facile and highly efficient synthesis of 4-thiazolidinones under solvent free conditions
  作者：Mahendra A. Chaudhari、Jitendra B. Gujar、Deepak S. Kawade、Pravin V. Shinde、Murlidhar S. Shingare

  DOI：10.1007/s11164-015-2010-9

  日期：2015.12

  A one-pot, multi-component, green, and highly efficient procedure has been developed for synthesis of 4-thiazolidinones. Use of β-cyclodextrin-SO3H as an eco-friendly and recyclable catalyst resulted in excellent yields under solvent-free conditions. This procedure has the advantages of readily available starting materials, short reaction times, high yields, easy workup, broad substrate scope, and use of an environment-friendly catalyst. The catalyst can be recycled with slight loss of its catalytic activity.

  开发了一种一锅法、多组分、绿色且高效的合成4-噻唑烷酮的工艺。使用β-环糊精-SO3H作为环保和可回收的催化剂，在无溶剂条件下获得了优异的产率。这一工艺具有原料易得、反应时间短、产率高、后处理简单、底物范围广以及使用环保催化剂等优点。该催化剂在回收时仅有轻微的催化活性损失。
• Visible-light-promoted C N and C S bonds formation: A catalyst and solvent-free photochemical approach for the synthesis of 1,3-thiazolidin-4-ones
  作者：Mohd Nazeef、Km Neha Shivhare、Shabir Ali、Khursheed Ansari、Mohd Danish Ansari、Saurabh K. Tiwari、Vikas Yadav、I.R. Siddiqui

  DOI：10.1016/j.jphotochem.2019.112347

  日期：2020.3

  A visible-light-induced, one-pot mild and efficient, multicomponent-tandem synthesis of diversified 1,3-thiazolidin-4-ones under catalyst and solvent-free conditions is reported. Here, visible-light, an ideal source of energy, has been used as photochemical activator to generate CN and CS bonds under radical mechanistic pathway from aromatic amines, aldehydes and thioglycolic acid. The reported methodology

  据报道，在无催化剂和无溶剂的条件下，可见光诱导的一锅式温和高效的多组分串联合成了多种1,3-噻唑烷酮-4-酮。在这里，可见光是一种理想的能源，已被用作光化学活化剂，通过自由基机制从芳族胺，醛和巯基乙酸生成C N和C S键。所报道的方法可以广泛地用于探索具有高选择性，短反应时间，对官能团的耐受性，成本效益和优异收率的1，3-噻唑烷丁-4-酮衍生物。
• Ultrasound assisted, VOSO4 catalyzed synthesis of 4-thiazolidinones: Antimicrobial evaluation of indazole-4-thiazolidinone derivatives
  作者：Srinivas Angapelly、P.V. Sri Ramya、Routhu SunithaRani、C. Ganesh Kumar、Ahmed Kamal、Mohammed Arifuddin

  DOI：10.1016/j.tetlet.2017.10.070

  日期：2017.12

  shorter reaction time, high yields, low catalyst loading, and also the catalyst can be recovered and reused up to next four cycles without significant loss in catalytic activity. All the synthesized novel indazole compounds were evaluated for their antibacterial and anti-biofilm activities. Compounds 9n, 9o and 9q showed promising activity (MIC value of 3.9 µg/mL) against K. planticola (MTCC 530). They

  通过在超声辐射下采用VOSO 4作为催化剂，开发了一种简单且方便的多组分方案以合成4-噻唑烷酮。该方案的重要特征包括较短的反应时间，高收率，较低的催化剂负载量，并且该催化剂可以回收并重复使用至下一个四个循环，而不会显着降低催化活性。对所有合成的新型吲唑化合物的抗菌和抗生物膜活性进行了评估。化合物9n，9o和9q表现出有希望的杀灭K. planticola（MTCC 530）的活性（MIC值为3.9 µg / mL ）。它们还显示出对K. planticola的显着杀菌活性。（MTCC 530）（MBC值为15.6 µg / mL）。另外，该生物体中9n，9o和9q抑制生物膜形成（IC 50值在20.28–20.79μg/ mL之间）。