3-[2-(4-氧代-2-苯基-1,3-噻唑烷-3-基)乙基]-2-苯基-1,3-噻唑烷-4-酮 | 91122-51-9

• 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: 3-[2-(4-氧代-2-苯基-1,3-噻唑烷-3-基)乙基]-2-苯基-1,3-噻唑烷-4-酮
• 英文名称: 3,3'-(ethane-1,2-diyl)bis(2-phenylthiazolidin-4-one)
• 英文别名: 1,2-bis-(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)ethane；1,2-bis(2-phenyl-4-thiazolidinone-3-yl)ethane；2,2'-diphenyl-3,3'-ethane-1,2-diyl-bis-thiazolidin-4-one；1,2-Bis(2-phenylthiazolidin-4-on-3-yl)ethane；4-Thiazolidinone, 3,3'-(1,2-ethanediyl)bis[2-phenyl-；3-[2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)ethyl]-2-phenyl-1,3-thiazolidin-4-one
• CAS: 91122-51-9
• 化学式: C₂₀H₂₀N₂O₂S₂
• 分子量: 384.523
• InChiKey: JDXXRAJDMGVZCQ-UHFFFAOYSA-N

物化性质

• 熔点：
  207.5-208 °C
• 沸点：
  670.1±55.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(4-氧代-2-苯基-1,3-噻唑烷-3-基)乙基]-2-苯基-1,3-噻唑烷-4-酮 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-bromo-5-[bromo(phenyl)methyl]-3-[2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)ethyl]-2-phenyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Sahu, J.; Sahu, T. K.; Naik, S. K., Journal of the Indian Chemical Society, 1983, vol. 60, p. 861 - 863

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 、 苯 为溶剂， 反应 0.25h， 生成 3-[2-(4-氧代-2-苯基-1,3-噻唑烷-3-基)乙基]-2-苯基-1,3-噻唑烷-4-酮
  参考文献：
  名称：

  新型1,2-双-（2-杂芳基-4-氧杂噻唑烷-3-基）乙烷和1,4-双-（2-杂杂芳基-4-氧杂唑烷-3-基）丁烷的合成及光谱数据

  摘要：

  新的αω-双-（-（2-杂芳基-4-氧杂噻唑烷-3-基）烷烃是通过常规的两步程序，使用N，N-双-偏二烯胺与α-巯基乙酸缩合而制备的。所用的双-醛亚胺是从乙二胺或腐胺与苯甲醛或异构化吡啶羧醛之间的反应获得的。该双- （2-苯基-4- oxothiazolidin -3-基）烷烃通过一锅二胺，醛和α-巯基乙酸的非常温和的条件下三个组分反应制备。

  DOI：

  10.1002/jhet.5570430228

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。
• Nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane as high-performance catalyst for the preparation of bis-thiazolidinones under ultrasonic conditions
  作者：Javad Safaei-Ghomi、Seyed Hadi Nazemzadeh、Hossein Shahbazi-Alavi

  DOI：10.1515/znb-2017-0091

  日期：2017.12.20

  We report a class of organic–inorganic hybrid material based on nano-colloidal silica-tethered polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane [nano-colloidal silica@APTPOSS (a series of polyhedral oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane)]. It was characterized by ¹H NMR spectroscopy, dynamic light scattering, scanning electron microscope, energy dispersive spectroscopy and thermogravimetric analysis. An easy and rapid method for the synthesis of bis-thiazolidinones has been presented by one-pot pseudo-five-component reaction of benzaldehydes, ethylenediamine and 2-mercaptoacetic acid using nano-colloidal silica@APTPOSS. The reusability of the catalyst and little catalyst loading, excellent yields, short reaction times, using the sonochemical procedure as a green process and an alternative energy source are some benefits of this method.

  我们报道了一类基于纳米胶体二氧化硅-连接的八支3-氨丙基三乙氧基硅烷聚合物的有机-无机杂化材料[nano-colloidal silica@APTPOSS（一系列八支3-氨丙基三乙氧基硅烷聚合物的聚合物八面体硅氧烷）]。它通过1H NMR光谱、动态光散射、扫描电子显微镜、能量色散谱和热重分析进行表征。使用nano-colloidal silica@APTPOSS，通过一锅伪五组分反应的简易快速方法合成了双噻唑烷酮。反应的五个组分是苯甲醛、乙二胺和2-巯基乙酸。该方法的优点包括催化剂的可重复使用性和少量催化剂负载、产率高、反应时间短、使用超声波程序作为绿色工艺和替代能源来源。

• Nano-CdZr₄(PO₄)₆ as a reusable and robust catalyst for the synthesis of bis-thiazolidinones by a multicomponent reaction of aldehydes, ethylenediamine and thioglycolic acid
  作者：Javad Safaei-Ghomi、Seyed Hadi Nazemzadeh、Hossein Shahbazi-Alavi

  DOI：10.1080/17415993.2016.1267176

  日期：2017.3.4

  used as an efficient catalyst for the preparation of bis-thiazolidinones by pseudo-five-component reaction of aldehydes, ethylenediamine and thioglycolic acid under reflux conditions in toluene. The present synthetic protocol has several advantages, such as simplicity, excellent yields, short reaction times, reusability of the catalyst and low catalyst loading. GRAPHICAL ABSTRACT

  摘要 Nano-CdZr4(PO4)6 已被用作一种有效的催化剂，通过醛、乙二胺和巯基乙酸在甲苯中回流条件下的假五组分反应制备双噻唑烷酮。目前的合成方案有几个优点，例如简单、产率高、反应时间短、催化剂的可重复使用性和低催化剂负载。图形概要
• Synthesis of Bis-Thiazolidinones Using Chitosan-attached Nano-CuFe₂ O₄ as an Efficient and Retrievable Heterogeneous Catalyst
  作者：Javad Safaei-Ghomi、Hossein Shahbazi-Alavi、Seyed Hadi Nazemzadeh

  DOI：10.1002/jccs.201700106

  日期：2017.10

  conditions in toluene. The catalyst was characterized by powder X‐ray diffraction (XRD), scanning electronic microscopy (SEM), vibrating sample magnetometer (VSM) measurements, thermal gravimetric analysis (TGA), and FT‐IR spectroscopy. This method provides several advantages including excellent yields, wide range of products, reusability of the catalyst, and a low amount of the catalyst.

  双噻唑烷酮的制备是通过在甲醛回流条件下，在纳米CuFe 2 O 4壳聚糖存在下，通过芳族醛，乙二胺和2-巯基乙酸的一锅缩合反应而实现的。催化剂的特征在于粉末X射线衍射（XRD），扫描电子显微镜（SEM），振动样品磁力计（VSM）测量，热重分析（TGA）和FT-IR光谱学。该方法具有几个优点，包括优异的产率，广泛的产物范围，催化剂的可重复使用性和少量的催化剂。
• Ultrasound‐Assisted Facile Synthesis and Antimicrobial Studies of Alkanediyl‐bis‐thiazolidin‐4‐ones and Alkanediyl‐bis‐thiazinan‐4‐ones
  作者：Amritpal Kaur、Avneet Pal Kaur、Poonam Gautam、Deepika Gautam、Ram Pal Chaudhary

  DOI：10.1002/jhet.3590

  日期：2019.8

  Alkanediyl‐bis‐2‐aryl‐thiazolidin‐4‐one and alkanediyl‐bis‐2‐aryl‐1,3‐thiazinan‐4‐one derivatives have been congregated in a single step reaction of diaminoalkanes, aryl aldehydes, and sulfanyl acids in the presence of coupling agent N,N′‐dicyclohexylcarbodiimide under ultrasonic conditions. This method of constructing 4‐keto derivatives of thiazolidine and thiazinane is quick and clean besides yielding

  烷二基双-2-芳基噻唑烷-4-酮和链烷二基双-2-芳基-1,3-噻嗪酮-4-酮衍生物在二氨基链烷烃，芳基醛和硫烷基酸的一步反应中聚集在一起超声条件下偶联剂N，N'-二环己基碳二亚胺的存在。这种构建噻唑烷和噻嗪烷的4-酮衍生物的方法除了可定量获得产物外，它还快速，清洁。光谱技术证实了分离产物的结构。也已经报道了合成产物的生物学测定。