ethyl (E)-3-((Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl)-3-phenyl-2-propenoate | 1278534-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-((Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl)-3-phenyl-2-propenoate
• 英文别名: ethyl (E)-3-[(5Z)-5-benzylidene-2,4-dioxo-1,3-thiazolidin-3-yl]-3-phenylprop-2-enoate
• CAS: 1278534-09-0
• 化学式: C₂₁H₁₇NO₄S
• 分子量: 379.436
• InChiKey: LRHRFGXSSFJXPI-KJTJFMRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-5-benzylidene-1,3-thiazolidine-2,4-dione 、 苯丙炔酸乙酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以73%的产率得到ethyl (E)-3-((Z)-5-benzylidene-2,4-dioxothiazolidin-3-yl)-3-phenyl-2-propenoate
  参考文献：
  名称：

  Triphenylphosphine-mediated chemoselective synthesis of functionalized thiazol-2(5H)-ones

  摘要：

  Stabilized phosphoranes, obtained from three-component reaction between dialkyl acetylenedicarboxylates and thiazolidine-2,4-dione in the presence of triphenylphosphine, undergo a smooth intramolecular Wittig reaction in boiling toluene to produce functionalized thiazol-2(5H)-ones in good yields. When alkyl propiolates were employed in these reactions, only the (E)-isomer of alkyl 3-(2,4-dioxothiazolidin-3-yl)acrylates were isolated. A dynamic effect was observed in the (1)H nuclear magnetic resonance (NMR) spectrum of ethyl (E)-3-(2,4-dioxothiazolidin-3-yl)-3-phenylacrylate as a result of restricted rotation (Delta G(not equal) = 77 kJ/mol) around the N-C bond between the thiazolidine moiety and the vinyl group.

  DOI：

  10.1007/s00706-010-0434-x