3-(benzo[d]thiazol-2-yl)-2-phenylthiazolidin-4-one | 69791-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(benzo[d]thiazol-2-yl)-2-phenylthiazolidin-4-one
• 英文别名: 3-benzothiazol-2-yl-2-phenylthiazolidin-4-one；2-[2'-(phenyl)-5'-oxo-1',3'-thiazolidine]-1,3-benzothiazole；2-[2'-phenyl-4'-oxo-1',3'-thiazolidine]-1,3-benzothiazole；3-Benzothiazol-2-yl-2-phenyl-thiazolidin-4-one；3-(1,3-benzothiazol-2-yl)-2-phenyl-1,3-thiazolidin-4-one
• CAS: 69791-48-6
• 化学式: C₁₆H₁₂N₂OS₂
• 分子量: 312.416
• InChiKey: FVPUXMIHNOBJMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(benzo[d]thiazol-2-yl)-2-phenylthiazolidin-4-one 、 苯甲醛 在 potassium ethoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以58%的产率得到2-[4'-benzylidene-2'-phenyl-5'-oxo-1',3'-thiazolidine]-1,3-benzothiazole
  参考文献：
  名称：

  A Comparative Study of the Inclusion Complexes of 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(p-N,N-dimethylamino- benzylidene)-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole withβ-Cyclodextrin

  摘要：

  化合物2-[5'-苄亚甲基-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑和2-[5'-(p-N, N-二甲基氨基苄亚甲基)-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑已从2-氨基苯并噻唑纯化形成。上述化合物的包含复合物已与β-环糊精制备，以增加它们在极性介质中的溶解度和生物可及性。通过在包含复合物形成前后研究光谱特征来确定包含复合物的形成。通过测定热力学参数确定包含复合物的稳定性和宿主与客体之间的相互作用性质。进一步测定了化合物的抗菌和抗真菌活性，发现在包含复合物形成后显著增加。

  DOI：

  10.1155/2011/265484
• 作为产物：
  描述：

  2-氨基苯并噻唑 在 溶剂黄146 、 zinc(II) chloride 作用下， 以 甲醇 、 苯 为溶剂， 反应 16.0h， 生成 3-(benzo[d]thiazol-2-yl)-2-phenylthiazolidin-4-one
  参考文献：
  名称：

  A Comparative Study of the Inclusion Complexes of 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(p-N,N-dimethylamino- benzylidene)-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole withβ-Cyclodextrin

  摘要：

  化合物2-[5'-苄亚甲基-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑和2-[5'-(p-N, N-二甲基氨基苄亚甲基)-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑已从2-氨基苯并噻唑纯化形成。上述化合物的包含复合物已与β-环糊精制备，以增加它们在极性介质中的溶解度和生物可及性。通过在包含复合物形成前后研究光谱特征来确定包含复合物的形成。通过测定热力学参数确定包含复合物的稳定性和宿主与客体之间的相互作用性质。进一步测定了化合物的抗菌和抗真菌活性，发现在包含复合物形成后显著增加。

  DOI：

  10.1155/2011/265484

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 Comparative Study of the Inclusion Complexes of 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(<i>p-N,N</i>-dimethylamino- benzylidene)-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole withβ-Cyclodextrin
  作者：S. Panda、S. K. Dash

  DOI：10.1155/2011/265484

  日期：——

  The compounds 2-[5'-benzylidene-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole and 2-[5'-(p-N,N-dimethylamino- benzylidene)-2'-phenyl-4'-oxo-1', 3'-thiazolidine]-1, 3-benzothiazole have been synthesized in their purest forms starting from 2-aminobenzothiazole. The inclusion complexes of the above compounds have been prepared with β-cyclodextrin to increase their solubility and bioaccessibility in polar medium. The formation of inclusion complexes have been ascertained by study of spectral characteristic before and after inclusion complex formation. The stability of inclusion complexes and nature of interaction between the host and guest are known from the determination of thermodynamic parameters. Further the antibacterial and antifungal activities of the compounds are determined which is found to increase significantly after inclusion complex formation

  化合物2-[5'-苄亚甲基-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑和2-[5'-(p-N, N-二甲基氨基苄亚甲基)-2'-苯基-4'-氧代-1', 3'-噻唑烷]-1, 3-苯并噻唑已从2-氨基苯并噻唑纯化形成。上述化合物的包含复合物已与β-环糊精制备，以增加它们在极性介质中的溶解度和生物可及性。通过在包含复合物形成前后研究光谱特征来确定包含复合物的形成。通过测定热力学参数确定包含复合物的稳定性和宿主与客体之间的相互作用性质。进一步测定了化合物的抗菌和抗真菌活性，发现在包含复合物形成后显著增加。
• MgO NPs Catalyzed Eco‐friendly Reaction: A Highly Effective and Green Approach for the Multicomponent One‐pot Synthesis of Polysubstituted Pyridines using 2‐Aminobenzothiazole
  作者：Divyani Gandhi、Shikha Agarwal

  DOI：10.1002/jhet.3384

  日期：2018.12

  A one‐pot multicomponent green and environmentally friendly synthesis of 5‐amino‐3‐benzothiazol‐2‐yl‐7‐(phenyl)‐2‐phenyl‐2,3‐dihydro‐thiazolo[4,5‐b]pyridine‐6‐carbonitrile via Knoevenagel condensation followed by Michael addition has been described in the presence of a green, low‐cost, mild, and efficient magnesium oxide as the heterogeneous base catalyst. The present methodology has attractive features

  一锅多组分绿色环保的5-氨基-3-苯并噻唑-2-基-7-（苯基）-2-苯基-2-3,2-二氢噻唑并[4,5-b]吡啶-6的合成方法在存在绿色，低成本，温和且有效的氧化镁作为非均相基础催化剂的情况下，已经描述了通过Knoevenagel缩合后的甲腈生成的甲腈。本方法具有吸引人的特征，例如优异的产物收率，对环境无害的温和反应条件，使用无毒有机溶剂以及易于回收和可重复使用的纳米催化剂。合成的化合物已通过光谱分析（傅立叶红外光谱，1 H-NMR，13 C-NMR和质谱法）确认。
• Srivastava; Shukla, Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 306 - 309
  作者：Srivastava、Shukla

  DOI：——

  日期：——
• HASSAN K. M.; MAHMOUD A. M.; EL-SHERIEF H. A., Z. NATURFORSCH., 1978, B 33, NO 9, 1005-1008
  作者：HASSAN K. M.、 MAHMOUD A. M.、 EL-SHERIEF H. A.

  DOI：——

  日期：——