2-(4-chlorophenyl)-3-(p-tolyl)thiazolidin-4-one | 299954-51-1

• 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-chlorophenyl)-3-(p-tolyl)thiazolidin-4-one
• 英文别名: 2-(4-chlorophenyl)-3-p-tolylthiazolidin-4-one；2-(4-Chlorophenyl)-3-(4-methylphenyl)-1,3-thiazolidin-4-one
• CAS: 299954-51-1
• 化学式: C₁₆H₁₄ClNOS
• 分子量: 303.812
• InChiKey: CSRFKIZVTIGBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 乙烷,三氯氟- 、 巯基乙酸 在 三乙胺硫酸盐 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以94%的产率得到2-(4-chlorophenyl)-3-(p-tolyl)thiazolidin-4-one
  参考文献：
  名称：

  1,3-噻唑烷-4-酮作为抗结核药的简便合成

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2016.02.056

文献信息

• 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。
• One-pot rapid synthesis of thiazole-substituted pyrazolyl-4-thiazolidinones mediated by diisopropylethylammonium acetate
  作者：Lalit D. Khillare、Manisha R. Bhosle、Amarsinh R. Deshmukh、Ramrao A. Mane

  DOI：10.1007/s11164-015-1940-6

  日期：2015.11

  A convenient one-pot, rapid and scalable synthetic protocol has been developed for recently reported anti-inflammatory agents, thiazole-substituted pyrazolyl-4-thiazolidinones. Quantitative multicomponent cyclocondensation of 3-(4-methyl-2-substituted thiazol-5-yl)-1-phenyl-1H-pyrazole-4-carbaldehydes (5a, b), amines and mercaptoacetic acid has been carried out in safer medium, diisopropylethylammonium acetate, at room temperature. The optimisation details of the developed novel protocol are recorded.

  一种方便的一锅法、快速且可扩展的合成方案已被开发，用于最近报道的抗炎药物，即噻唑取代的吡唑-4-噻唑烷酮。对3-(4-甲基-2-取代噻唑-5-基)-1-苯基-1H-吡唑-4-醛（5a, b）、胺和巯基乙酸的定量多组分环缩合反应已在更安全的介质二异丙基乙胺乙酸盐中于室温下进行。所开发的新型方案的优化细节已记录。
• Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside–thiazolidinone hybrids and their antiparasitic activities
  作者：Xinying Zhang、Xiaoyan Li、Dongfang Li、Guirong Qu、Jianji Wang、Philippe M. Loiseau、Xuesen Fan

  DOI：10.1016/j.bmcl.2009.09.101

  日期：2009.11

  acid in [bmim][PF6]. The whole procedure is simple and straightforward and no aqueous work-up is needed. By employing this protocol, a series of novel pyrimidine nucleoside–thiazolidin-4-one hybrids were prepared and their preliminary antiparasitic activities were also studied and reported.

  在没有任何催化剂的情况下，通过醛，胺和巯基乙酸在[bmim] [PF 6 ]中的三组分反应，可以有效地合成2,3-二取代-1,3-噻唑烷-4-酮衍生物。整个过程简单明了，不需要水后处理。通过采用该方案，制备了一系列新型嘧啶核苷-噻唑烷-4-酮杂化物，并对其初步的抗寄生虫活性进行了研究和报道。
• Preparation of thiazolidin-4-one derivatives using ZnO–NiO–NiFe2O4 nano-composite system
  作者：Mojtaba Lashkari、Majid Ghashang

  DOI：10.1007/s11164-020-04287-5

  日期：2021.2

  The hydrothermal synthesis of ZnO–NiO–NiFe2O4 nano-composite is reported. The sample was utilized to characterize via XRD, FE-SEM, EDS, FT-IR, UV–Vis, and BET techniques. The sample consisted of three different phases as ZnO (hexagonal), NiO (cubic), and NiFe2O4 (cubic) with the average particle size as 34 nm and specific surface area, average pore diameter, and pore volume as 64.35 m2 g−1, 13.02 nm

  据报道水热合成了ZnO–NiO–NiFe 2 O 4纳米复合材料。该样品用于通过XRD，FE-SEM，EDS，FT-IR，UV-Vis和BET技术进行表征。样品由三个不同的相组成，分别为ZnO（六方），NiO（立方）和NiFe 2 O 4（立方），平均粒径为34 nm，比表面积，平均孔径和孔体积为64.35 m 2 克-1，13.02纳米，0.201厘米3 克-1， 分别。研究了纳米复合材料在热和超声辐照条件下合成噻唑烷丁-4-酮衍生物的催化行为。我们的结果表明，ZnO–NiO–NiFe 2 O 4纳米复合材料的催化活性远高于ZnO，NiO和NiFe 2 O 4金属氧化物。所有产品均以高收率和较短的反应时间制备。另外，催化剂被回收至少五次。