4,4'-(pyridin-2-ylmethylene)dimorpholine | 53189-78-9

• 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: 4,4'-(pyridin-2-ylmethylene)dimorpholine
• 英文别名: dimorpholinomethyl-2 pyridine；4,4'-pyridin-2-ylmethanediyl-bis-morpholine；4-[Morpholin-4-yl(pyridin-2-yl)methyl]morpholine
• CAS: 53189-78-9
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: MTQKWTQKEVGBSK-UHFFFAOYSA-N

物化性质

• 沸点：
  362.3±42.0 °C(Predicted)
• 密度：
  1.223 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  5

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：

  在 甲烷磺酸 作用下， 以 氘代乙腈 为溶剂， 反应 48.0h， 生成 4,4'-(pyridin-2-ylmethylene)dimorpholine
  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

文献信息

• Molecular design and QSAR study of low acute toxicity biocides with 4,4′-dimorpholyl-methane core obtained by microwave-assisted synthesis
  作者：Raúl Hernández-Altamirano、Violeta Y. Mena-Cervantes、Sandra Perez-Miranda、Francisco J. Fernández、Cesar Andres Flores-Sandoval、Victor Barba、Hiram I. Beltrán、Luis S. Zamudio-Rivera

  DOI：10.1039/b905153h

  日期：——

  phenol (4c), 2,4-di-tert-butyl-6-(dimorpholinomethyl)-phenol (4d), 4,4′-(pyridin-2-ylmethylene)-dimorpholine (4e), 4,4′-((4-iso-propylphenyl)methylene)-dimorpholine (4f), 4,4′-(naphthalen-1-ylmethylene)-dimorpholine (4g) and 4,4′-(pyren-1-ylmethylene)-dimorpholine (4h). Additionally, single crystal X-ray diffraction analysis for 4b, 4c, 4d and 4e derivatives was accomplished showing interesting geometrical

  微波无溶剂合成醛（1a，2b–h）和吗啉（3）在1 ：2（醛 ： 吗啉）比率产生8种4,4'-二吗啉基甲烷（4a - 4h），通过以下方法对其进行了彻底表征红外光谱，1小时，13 ℃ 和 二维核磁共振，确认类型4的结构。所描述的化合物是双吗啉代--甲烷（4a），2-（二吗啉代甲基）苯酚（4b），4-溴-2-（二吗啉代甲基）苯酚（4c），2,4-二叔丁基-6-（二吗啉代甲基）苯酚（4d），4,4'-（吡啶-2-基亚甲基）-二吗啉（4e），4,4' - （（4-异丙-propylphenyl）亚甲基）-dimorpholine（4f），4,4'-（萘-1-基亚甲基）-二吗啉（4克）和4,4'-（吡喃-1-基亚甲基）-二吗啉（4h）。此外，单晶X射线衍射对4b，4c，4d和4e导数的分析已完成，显示了有趣的几何特征。对获得的4,4'-二吗啉基甲烷进行了两项生物学测试，（i）急性毒性，与发光细菌（fibrio
• Aube, Philippe; Christot, Isabelle; Combret, Jean-Claude, Bulletin de la Societe Chimique de France, 1988, # 6, p. 1009 - 1014
  作者：Aube, Philippe、Christot, Isabelle、Combret, Jean-Claude、Klein, Jean-Louis

  DOI：——

  日期：——
• Duhamel,L. et al., Bulletin de la Societe Chimique de France, 1974, p. 331 - 337
  作者：Duhamel,L. et al.

  DOI：——

  日期：——