tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate | 864515-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
• CAS: 864515-97-9
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: VMRGTHKRAOTTBX-MRVPVSSYSA-N

物化性质

• 沸点：
  330.9±42.0 °C(predicted)
• 密度：
  1.053±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate 在 异丙基氯化镁 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.75h， 生成 (2R,3S)-2-benzyl-N-methoxy-N,3-dimethyl-5-oxoheptanamide
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q
• 作为产物：
  描述：

  叔丁基3-氧代戊酸乙酯 在 [Ni((S)-Tol-BINAP)]OTf₂ 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
  参考文献：
  名称：

  Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Reactions of β-Ketoesters and Unsaturated N-Acylthiazolidinethiones

  摘要：

  The enantioselective addition of beta-ketoesters to unsaturated N-acylthiazolidinethiones catalyzed by Ni(II) Tol-BINAP Lewis acid complexes is reported. Notable features of this reaction are its operation simplicity, the obviated need for the addition of an external base, and the ease with which the adducts are converted into a range of potentially useful derivatives. In particular, the dihydropyrone adducts are versatile scaffolds for further stereoselective elaboration.

  DOI：

  10.1021/ja053820q