dimethyl (E)-2-(2,5-dihydro-2-oxothiazol-4-yl)butenedioate | 1278533-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (E)-2-(2,5-dihydro-2-oxothiazol-4-yl)butenedioate
• 英文别名: dimethyl (E)-2-(2-oxo-5H-1,3-thiazol-4-yl)but-2-enedioate
• CAS: 1278533-91-7
• 化学式: C₉H₉NO₅S
• 分子量: 243.24
• InChiKey: SYKBNXPUXOIBQL-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 丁炔二酸二甲酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以67%的产率得到dimethyl (E)-2-(2,5-dihydro-2-oxothiazol-4-yl)butenedioate
  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