3-(p-chlorophenyl)-2-(diacetylmethylidene)-1,3-thiazolidine-4,5-dione | 1104641-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(p-chlorophenyl)-2-(diacetylmethylidene)-1,3-thiazolidine-4,5-dione
• 英文别名: 3-(4-chlorophenyl)-2-(2,4-dioxopentan-3-ylidene)-1,3-thiazolidine-4,5-dione
• CAS: 1104641-77-1
• 化学式: C₁₄H₁₀ClNO₄S
• 分子量: 323.757
• InChiKey: AYLXQHJTAQJKJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(p-chlorophenyl)-2-(diacetylmethylidene)-1,3-thiazolidine-4,5-dione 、 溴乙酸乙酯 以 甲苯 为溶剂， 反应 2.0h， 以50%的产率得到2-acetylmethylidene-3-(p-chlorophenyl)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  N-芳基二乙酰基硫代乙酰胺的酮-烯醇平衡及其反应性的光谱研究

  摘要：

  An NMR study of the equilibrium between keto-enol tautomeric forms of N-aryl-diacetylthioacetamides enables us to estimate their population ratio in solvents of increasing polarity. An X-ray analysis confirmed the structure of the thermodynamically most stable tautomer. We presume that the course of heterocyclization processes with N-aryldiacetylthioacetamides is affected by the structure of the reacting tautomeric form. The treatment of N-aryldiacetylthioacetamides with oxalyl or bromoacetyl bromides leads to thiazolidine derivatives. The reactivity of the 5-methylene group in the obtained thiazolidin-4-one derivatives was investigated.

  DOI：

  10.1007/s10593-008-0051-3
• 作为产物：
  描述：

  草酰氯 、 α-Acetylacetthioessigsaeure-(4-chlor-anilid) 以 甲苯 为溶剂， 以70%的产率得到3-(p-chlorophenyl)-2-(diacetylmethylidene)-1,3-thiazolidine-4,5-dione
  参考文献：
  名称：

  N-芳基二乙酰基硫代乙酰胺的酮-烯醇平衡及其反应性的光谱研究

  摘要：

  An NMR study of the equilibrium between keto-enol tautomeric forms of N-aryl-diacetylthioacetamides enables us to estimate their population ratio in solvents of increasing polarity. An X-ray analysis confirmed the structure of the thermodynamically most stable tautomer. We presume that the course of heterocyclization processes with N-aryldiacetylthioacetamides is affected by the structure of the reacting tautomeric form. The treatment of N-aryldiacetylthioacetamides with oxalyl or bromoacetyl bromides leads to thiazolidine derivatives. The reactivity of the 5-methylene group in the obtained thiazolidin-4-one derivatives was investigated.

  DOI：

  10.1007/s10593-008-0051-3