3-苄基-2-苯基-1,3-噻唑烷-4-酮 | 80353-43-1

• 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-苄基-2-苯基-1,3-噻唑烷-4-酮
• 英文名称: 3-benzyl-2-phenyl-1,3-thiazolidin-4-one
• 英文别名: 3-benzyl-2-phenylthiazolidin-4-one；3-benzyl-2-phenyl-thiazolidin-4-one；3-Benzyl-2-phenyl-thiazolidin-4-on
• CAS: 80353-43-1
• 化学式: C₁₆H₁₅NOS
• mdl: MFCD00432644
• 分子量: 269.367
• InChiKey: LIDAKPFOOTZNRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  492.1±45.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)
• 溶解度：
  31.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-苄基-2-苯基-1,3-噻唑烷-4-酮 在 triethylamine tris(hydrogen fluoride) 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 75.0h， 生成 3-benzyl-5-fluoro-1,1-dioxo-2-phenyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Electrolytic partial fluorination of organic compounds. 4. Regioselective anodic monofluorination of 4-thiazolidinones and its application to the synthesis of monofluoro .beta.-lactams

  摘要：

  Anodic partial fluorination of sulfur-containing heterocycles has been performed for the first time: 2-aryl-4-thiazolidinones 1 were monofluorinated highly regioselectively. In addition, thermolysis of the sulfones derived from fluorinated 1 provided monofluoro beta-lactams in excellent yields.

  DOI：

  10.1021/jo00040a003
• 作为产物：
  描述：

  N-benzyl-2-[[2-(benzylamino)-2-oxoethyl]sulfanyl-phenylmethyl]sulfanylacetamide 在 calcium carbonate 、 mercury dichloride 作用下， 以 乙腈 为溶剂， 以29%的产率得到3-苄基-2-苯基-1,3-噻唑烷-4-酮
  参考文献：
  名称：

  4-Thiazolidinone Synthesis: Mercury-Assisted Elimination-Cyclization of Bis[aminocarbonylmethyl]S,S-Acetals

  摘要：

  DOI：

  10.1055/s-1981-29614

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。
• A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4·5H2O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid
  作者：Hai-Xia Pang、Yong-Hai Hui、Kui Fan、Xue-Jian Xing、Yang Wu、Jing-Hui Yang、Wei Shi、Zheng-Feng Xie

  DOI：10.1016/j.cclet.2015.10.029

  日期：2016.3

  Mesoporous MCM-41 supported Schiff base and CuSO4·5H2O shows high catalytic activity in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford pharmaceutically important thiazolidinone derivatives. The catalytic reactions involving two-components or three-components afforded the desired product in high yields (up to 98% and 99%). Moreover, the catalyst works well

  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％。
• Visible-light-driven photocatalytic activity of ZnO/g-C3N4 heterojunction for the green synthesis of biologically interest small molecules of thiazolidinones
  作者：Robabeh Mohammadi、Hassan Alamgholiloo、Behnam Gholipour、Sadegh Rostamnia、Samad Khaksar、Mustafa Farajzadeh、Mohammadreza Shokouhimehr

  DOI：10.1016/j.jphotochem.2020.112786

  日期：2020.11

  properties including high surface area, high loading, extraordinary electronic properties, and easy separation for increases photocatalytic performance has remained a challenge in photocatalytic applications. Herein, an environmentally benign approach was developed to fabricate graphitic carbon nitride (g-C3N4) decorated with nanorods zinc oxide (ZnO). The photocatalytic activity of ZnO decorated on the

  设计具有互补特性的光催化体系，包括高表面积，高负载，非凡的电子特性以及易于分离以提高光催化性能，一直是光催化应用中的挑战。在本文中，开发了一种环境友好的方法来制造装饰有纳米棒氧化锌（ZnO）的石墨氮化碳（gC 3 N 4）。装饰在gC 3 N 4上的ZnO的光催化活性在非常温和且可持续的反应条件下，在合成1,3-噻唑烷酮-4-酮和双噻唑烷酮中形成了表面。该反应可以通过利用可见光来进行，而不需要任何添加剂和其他外部能源。发现所提出的光催化剂是更容易使用，可回收利用的大规模应用，并且为各种应用中的半导体稳定化提供了一些新见识。
• Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot three-component condensation
  作者：Tumul Srivastava、W Haq、S.B Katti

  DOI：10.1016/s0040-4020(02)00866-9

  日期：2002.9

  In the present study, 4-thiazolidinones have been assembled by DCC mediated three-component reaction of amine, aldehyde and mercaptoacetic acid. The final compounds are obtained in quantitative yields within one hour.

  在本研究中，4-噻唑烷酮已通过DCC介导的胺，醛和巯基乙酸的三组分反应组装。在一小时内以定量产率获得最终化合物。
• Catalyst-free and environment friendly synthesis of 2-aryl-3-substituted-4-thiazolidinones in water
  作者：Manoj P. Thakare、Rahimullah Shaikh、Dipak Tayade

  DOI：10.1039/c6ra02064j

  日期：——

  A simple, efficient, eco-friendly, and cost-effective method has been developed for the three component one pot synthesis of 2-aryl-3-substituted-4-thiazolidinones is described. The method provides rapid and easy access to thiazolidinone compounds in good to excellent yields.

  已经开发了一种简单，有效，环保且经济高效的方法，用于描述3-芳基-3-取代的4-噻唑烷酮的三组分一锅合成。该方法提供了快速且容易获得噻唑烷酮化合物的方法，收率良好。