(E)-2-[(diethoxythiophosphoryl)thio]methylene-(Z)-5-(methoxycarbonylmethylene)thiazolidin-4-one | 1206719-18-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-2-[(diethoxythiophosphoryl)thio]methylene-(Z)-5-(methoxycarbonylmethylene)thiazolidin-4-one
• CAS: 1206719-18-7
• 化学式: C₁₁H₁₆NO₅PS₃
• 分子量: 369.423
• InChiKey: QAVODWUUDNAIRN-MKKAVFGOSA-N

反应信息

• 作为产物：
  描述：

  S-(2-amino-2-thioxoethyl) O,O-diethyl phosphodithioate 、 丁炔二酸二甲酯 以 氯仿 为溶剂， 反应 6.0h， 以57%的产率得到(E)-2-[(diethoxythiophosphoryl)thio]methylene-(Z)-5-(methoxycarbonylmethylene)thiazolidin-4-one
  参考文献：
  名称：

  Factors Determining the Stereochemical Structure of 2-(Phosphorus Substituted) Methylidene-thiazolidine- 4-ones in Solid State and in Solution

  摘要：

  Regioselective synthesis of novel 2-(phosphorus substituted) methylidene-thiazolidine-4-ones 5a-c was performed via condensation of phosphorus-substituted acetic acid thioamides 4a-c with dimethyl acetylenedicarboxylate. Thiazolidine-4-ones 5a,b bearing thiophosphoryl or dithiophosphoryl moiety were obtained as E,Z-isomers while their analog 5c with triphenylphosphonium group was formed as a Z,Z-isomer. The structures of thiazolidin-4-ones 5a-c obtained were determined by single crystal X-ray diffraction. According to quantum-chemical calculations, the isomers observed in the solid state are thermodynamically more stable. In solution, thio- and dithiophosphorylated thiazolidinones 5a, b undergo E,Z Z,Z isomerization relative to C2 carbon atom of the heterocycle proceeding via an imine-enamine mechanism.

  DOI：

  10.1080/10426500802715544