(1R*,2R*)-1,3-diethyl-4,6-dioxo-2-thioxo-5-[2-(triphenylphosphonio)-1,2-bis(tert-butoxycarbonyl)ethyl]tetrahydropyrimidin-5-ide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R*,2R*)-1,3-diethyl-4,6-dioxo-2-thioxo-5-[2-(triphenylphosphonio)-1,2-bis(tert-butoxycarbonyl)ethyl]tetrahydropyrimidin-5-ide
• 英文别名: 5-[(2S,3S)-1,4-bis[(2-methylpropan-2-yl)oxy]-1,4-dioxo-3-triphenylphosphaniumylbutan-2-yl]-1,3-diethyl-6-oxo-2-sulfanylidenepyrimidin-4-olate
• 化学式: C₃₈H₄₅N₂O₆PS
• 分子量: 688.825
• InChiKey: AVBRRHWFUHMRKG-VEEOACQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,3-二乙基-2-硫代巴比妥酸 、 丁炔二酸二叔丁酯 乙炔二羧酸二叔丁酯 、 三苯基膦 以 乙酸乙酯 为溶剂， 反应 0.73h， 生成 (1R*,2R*)-1,3-diethyl-4,6-dioxo-2-thioxo-5-[2-(triphenylphosphonio)-1,2-bis(tert-butoxycarbonyl)ethyl]tetrahydropyrimidin-5-ide 、 (1S*,2R*)-1,3-diethyl-4,6-dioxo-2-thioxo-5-[2-(triphenylphosphonio)-1,2-bis(tert-butoxycarbonyl)ethyl]tetrahydropyrimidin-5-ide
  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