diethyl 7-(2,6-dimethylphenylamino)-4-oxo-2-thio-1,3-diethyl-4H-pyrano[2,3-d]pyrimidine-5,6-dicarboxylate | 1237541-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: diethyl 7-(2,6-dimethylphenylamino)-4-oxo-2-thio-1,3-diethyl-4H-pyrano[2,3-d]pyrimidine-5,6-dicarboxylate
• CAS: 1237541-16-0
• 化学式: C₂₅H₃₁N₃O₆S
• 分子量: 501.604
• InChiKey: QPGNOQUMOGIJOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  100.79
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  1,3-二乙基-2-硫代巴比妥酸 、 2,6-xylyl isocyanide 、 丁炔二酸二乙酯 以 二氯甲烷 为溶剂， 反应 120.0h， 以87%的产率得到diethyl 7-(2,6-dimethylphenylamino)-4-oxo-2-thio-1,3-diethyl-4H-pyrano[2,3-d]pyrimidine-5,6-dicarboxylate
  参考文献：
  名称：

  异氰化物或三苯膦存在下活性乙炔与N,N'-二乙基-2-硫代巴比妥酸反应的研究

  摘要：

  AbstractIn a series of separate experiments reaction between N,N′‐diethyl‐2‐thiobarbituric acid and acetylenic diesters in the presence of isocyanides or triphenylphosphine led to highly functionalized 4H‐pyrano[2,3‐d]thiopyrimidine or 1,4‐di‐ionic organophosphorus derivatives. The 1H NMR spectra of diethyl‐7‐(2,6‐dimethylphenylamino)‐4‐oxo‐2‐thio‐ 1,3‐diethyl‐4H‐pyrano[2,3‐d]pyrimidine‐5,6‐dicarboxylate showed dynamic NMR effect that was attributed to restricted rotation around the aryl‐nitrogen single bond. Activation free energy (ΔG≠) for this process is about 54.85 ± 2 kJ mol−1. Betaines as 1,4‐diionic organophosphorus compounds in this reaction are possessed of two vicinal stereogenic centers and exist in the solution as a mixture of two diastereoisomers. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:228–235, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20601

  DOI：

  10.1002/hc.20601