diethyl 2,2-dimethyl-4-oxo-1,3-dihydropyridine-5,6-dicarboxylate | 89968-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2,2-dimethyl-4-oxo-1,3-dihydropyridine-5,6-dicarboxylate
• CAS: 89968-30-9
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: BDGMUPBSQRWAIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 diethyl 2,2-dimethyl-4-oxo-1,3-dihydropyridine-5,6-dicarboxylate 以 甲醇 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Resolution and racemization of nonbenzenoid atropenantiomers

  摘要：

  The three-step synthesis of adduct 3 has been reinvestigated; enantiomers 3a and 3b have been separated by enantio selective chromatography and the racemization barrier of 3a was determined as DeltaG(not equal) = 24.4 kcal mol(-1) (16 degreesC).

  DOI：

  10.1070/mc2004v014n06abeh002049
• 作为产物：
  描述：

  四甲基哌啶酮 在 氢气 作用下， 以 乙醚 为溶剂， 生成 diethyl 2,2-dimethyl-4-oxo-1,3-dihydropyridine-5,6-dicarboxylate
  参考文献：
  名称：

  Resolution and racemization of nonbenzenoid atropenantiomers

  摘要：

  The three-step synthesis of adduct 3 has been reinvestigated; enantiomers 3a and 3b have been separated by enantio selective chromatography and the racemization barrier of 3a was determined as DeltaG(not equal) = 24.4 kcal mol(-1) (16 degreesC).

  DOI：

  10.1070/mc2004v014n06abeh002049

文献信息

• Atropoenantiomerism of the Z-adduct of 2,3-diethoxycarbonyi-6,6-dimethyl-5,6-dihydro-4-pyridone with dimethyl acetylenedicarboxylate: synthesis and structure in solution and in the crystal
  作者：R. G. Kostyanovsky、Yu. I. El'natanov、I. I. Chervin、S. V. Konovalikhin、A. B. Zolotoi、L. O. Atovmyan

  DOI：10.1007/bf01431811

  日期：1996.7

  The title adduct (1) was synthesized, and its conformationally and configurationally rigid chiral structure in solution and in the crystal was established by NMR spectroscopy and by X-ray structural analysis. Atropoenantiomers of1 were observed by the1H NMR method in the presence of a chiral shift reagent. A barrier to their interconversïon was determined, ΔGx > Z5 kcal mol−1 (200 °C).

  合成了标题加合物 (1)，并通过 NMR 光谱和 X 射线结构分析确定了其在溶液和晶体中的构象和构型刚性手性结构。在手性位移试剂的存在下，通过 1 H NMR 方法观察到 1 的阻转对映异构体。确定了它们相互转化的障碍，ΔGx > Z5 kcal mol-1 (200 °C)。
• Resolution and racemization of nonbenzenoid atropenantiomers
  作者：Pavel V. Novikov、Oleg R. Malyshev、Konstantin A. Lyssenko、Remir G. Kostyanovsky

  DOI：10.1070/mc2004v014n06abeh002049

  日期：2004.1

  The three-step synthesis of adduct 3 has been reinvestigated; enantiomers 3a and 3b have been separated by enantio selective chromatography and the racemization barrier of 3a was determined as DeltaG(not equal) = 24.4 kcal mol(-1) (16 degreesC).