3-Phenyl-5-(2-phenyl-2-oxoethyl)-4-oxo-2-thioxo-1,3-thiazolidine | 302594-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Phenyl-5-(2-phenyl-2-oxoethyl)-4-oxo-2-thioxo-1,3-thiazolidine
• 英文别名: 5-phenacyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 302594-27-0
• 化学式: C₁₇H₁₃NO₂S₂
• 分子量: 327.428
• InChiKey: GRLPCOLYMJDSOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Phenyl-5-(2-phenyl-2-oxoethyl)-4-oxo-2-thioxo-1,3-thiazolidine 在 劳森试剂 作用下， 以 xylene 为溶剂， 反应 4.0h， 以92%的产率得到3,5-Diphenyl-2,3-dihydro-2-thioxothieno[2,3-d]thiazole
  参考文献：
  名称：

  A One-Pot Synthesis of 2,3-Dihydro-2-Thioxothieno[2,3-d]Thiazoles

  摘要：

  多种3,5-二取代-2,3-二氢-2-硫代噻吩[2,3-d]噻唑（3a-h），包括烷基、芳基和杂原子取代基，在优选的产率中通过一步反应合成了3-取代-5-(2-芳基（或杂原子）-2-氧代乙基)-4-氧代-2-硫代-1,3-噻唑烷（1a-h）与四磷酸十硫化物（方法A）或Lawesson试剂（方法B）的反应。然而，当(E,Z)-5-(2-芳基-2-氧代亚乙基)衍生物（2f,g）在与相同试剂反应时，也能得到相当产率的3以及未知油状产物。产物的结构得到了微观分析和光谱证据的支持。为转化的途径提供了合理的解释。

  DOI：

  10.1055/s-2001-11440
• 作为产物：
  描述：

  3-苯甲酰基-2-丙烯酸 、 铵苯基二硫代氨基甲酸酯 以 乙醇 为溶剂， 反应 0.5h， 以88%的产率得到3-Phenyl-5-(2-phenyl-2-oxoethyl)-4-oxo-2-thioxo-1,3-thiazolidine
  参考文献：
  名称：

  REACTIONS OF 5-SUBSTITUTED-2-THIOXO-4-OXO-1,3-THIAZOLIDINES WITH 4-METHOXYPHENYLAZIDE

  摘要：

  4-Methoxyphenylazide cycloadds to the thiono function and undergoes nucleophilic attack at other electrophilic centers of 5-benzoylmethyl- (la) and E,Z-5-(4-bromobenzoylmethylene)- (E,2-2b) -2-thioxo-4-oxo-1,3-thiazolidines in non site selective reactions to afford variety of products. With la, the attack at the thiono as well as the hetero-ring carbonyl functions leads to the 5-benzoylmethylene-2-(4-methoxyphenylimino)- derivative (3) and the ring fission product 2-4. Similar treatment of E,Z-2b gives a mixture of the respective E,Z-2-(4-methoxyphenylimino)derivative (E,Z-5) containing 80% of the IE-configurated isomer (Z-5) and the ring enlarged thiazinonethione derivative (6), due to the attack at the thiono and exocyclic double bond functions, respectively. Rationalizations for the above mentioned conversions are given. Structures of all products are evidenced by microanalytical and spectral data,The chemistry of 4-thiazolidinones has been a subject of a series of publications(1-6) from this laboratory, Reactions of 2-thioxo-4-thiazolidinones with dipolar species in the literature are rather limited and treat the problem of alkylation of the 3-unsubstituted derivatives with diazomethane(7,8), and cycloaddition of nitrilimines to the thiono function of 5-aroylmethylene-3-phenyl-2-thioxo-4-oxo-1,3-thiazolidine(9). The present work aimed to study the reactivity of different functions in 5-alkyl- and 5-alkylidene substituted thiazolidones namely 3-phenyl-5-(2-phenyl-2-oxoethyl)-(1a) and E,Z-3-benzyl-5-(4-bromophenylmethylene)-(E,Z-2b)-4-oxo-2-thioxo-1,3-thiazolidines towards reaction with 4-methoxyphenylazide.

  DOI：

  10.1080/10426500008045217