4-[Ethoxy(pyridin-2-yl)methyl]morpholine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-[Ethoxy(pyridin-2-yl)methyl]morpholine
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: QDWXZPQDJWKFAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-(pyridin-2-ylmethylene)dimorpholine 、 4-[Ethoxy(pyridin-2-yl)methyl]morpholine 在 甲烷磺酸 作用下， 以 氘代乙腈 为溶剂， 反应 24.0h， 以7%的产率得到吡啶-2-甲醛
  参考文献：
  名称：

  Reactivity-Based Dynamic Covalent Chemistry: Reversible Binding and Chirality Discrimination of Monoalcohols

  摘要：

  In an effort to develop reactivity-based dynamic covalent bonding and to expand the scope and application of the dynamic covalent chemistry, in situ-generated simple generic iminium ions were utilized for the dynamic covalent binding of monoalcohols with high affinity. Hammett analysis was conducted to manipulate the equilibrium and correlate with the reactivity of reactants. The structural features of aldehydes and secondary amines were identified, and both polar and steric effects have significant impact on the binding. In particular, the substrates which can participate in pi-pi and polar-pi interactions are able to afford apparent equilibrium constants in the magnitude of 104 M-2, demonstrating the power of weak supramolecular forces to stabilize the dynamic covalent assembly. The generality of the assembly was validated with a series of mono secondary alcohols. To showcase the practicality of our system, chirality discrimination and ee measurement of chiral secondary alcohols were achieved.

  DOI：

  10.1021/jo502801g
• 作为产物：
  描述：

  乙醇 、 4-<(benzotriazol-1-yl)(pyrid-2-yl)methyl>morpholine 在 sodium 作用下， 反应 4.0h， 以86%的产率得到4-[Ethoxy(pyridin-2-yl)methyl]morpholine
  参考文献：
  名称：

  A Convenient Synthesis ofN-(α-Alkoxyalkyl)- andN-[α-(Alkylthio)alkyl]amines

  摘要：

  在温和条件下，N-[1-(苯并三唑-1-基)烷基]胺对醇和硫醇进行氨烷基化，得到 N-(α-烷氧基烷基)胺 2 和 N-[α-(烷硫基)烷基]胺 3 ，分别获得良好的收益。

  DOI：

  10.1055/s-1993-25837