diethyl 1-octyl-4-oxo-1,4-dihydropyridine-3,5-dicarboxylate | 1325297-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: diethyl 1-octyl-4-oxo-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1325297-20-8
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: FZORQDXVCBOTRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 1-octyl-4-oxo-1,4-dihydropyridine-3,5-dicarboxylate 在 N-甲基吗啉 、 硫酸 、 氯甲酸乙酯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.92h， 生成 ethyl 5-amino-1-octyl-4-oxo-1, 4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Five-Fold-Symmetric Macrocyclic Aromatic Pentamers: High-Affinity Cation Recognition, Ion-Pair-Induced Columnar Stacking, and Nanofibrillation

  摘要：

  Described in this study is a conceptually new class of five-fold-symmetric cavity-containing planar pentameric macrocycles with their interior decorated by five convergently aligned, properly spaced carbonyl oxygen atoms. These cation-binding oxygens enclose a hydrophilic lumen of 2.85 angstrom in radius and thus display high-affinity binding toward alkali metal cations, and possibly many other cations, too. Arising from their high-affinity recognition of metal ions, these planar macrocycles form cation- or ion-pair-induced one-dimensional columnar aggregates, and subsequently fascinating fibrillation results.

  DOI：

  10.1021/ja206457b
• 作为产物：
  描述：

  1-溴辛烷 、 4-氧代-1,4-二氢-3,5-吡啶二羧酸二乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到diethyl 1-octyl-4-oxo-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Five-Fold-Symmetric Macrocyclic Aromatic Pentamers: High-Affinity Cation Recognition, Ion-Pair-Induced Columnar Stacking, and Nanofibrillation

  摘要：

  Described in this study is a conceptually new class of five-fold-symmetric cavity-containing planar pentameric macrocycles with their interior decorated by five convergently aligned, properly spaced carbonyl oxygen atoms. These cation-binding oxygens enclose a hydrophilic lumen of 2.85 angstrom in radius and thus display high-affinity binding toward alkali metal cations, and possibly many other cations, too. Arising from their high-affinity recognition of metal ions, these planar macrocycles form cation- or ion-pair-induced one-dimensional columnar aggregates, and subsequently fascinating fibrillation results.

  DOI：

  10.1021/ja206457b

文献信息

• Hybrid Pyridine–Pyridone Foldamer Channels as M2‐Like Artificial Proton Channels
  作者：Jie Shen、Ruijuan Ye、Zhiwei Liu、Huaqiang Zeng

  DOI：10.1002/anie.202200259

  日期：2022.7.11

  A mild and efficient PyBOP-mediated one-pot copolymerization generates a unique family of aromatic amide foldamer-based helically folded organic nanotubes. These channels facilitate ultrafast and exceptionally selective transmembrane proton transport that likely proceeds via an unprecedented transport mechanism, where a proton may create its own channel-spanning water chain from two or more short water

  温和有效的 PyBOP 介导的一锅共聚反应生成了一个独特的基于芳香酰胺折叠体的螺旋折叠有机纳米管家族。这些通道促进了超快和特别选择性的跨膜质子转运，这种转运可能通过一种前所未有的转运机制进行，质子可以从两条或更多短水链中创建自己的跨通道水链，以促进其自身的跨膜转运。
• Sulfur‐Containing Foldamer‐Based Artificial Lithium Channels
  作者：Jie Shen、Deepa R、Zhongyan Li、Hyeonji Oh、Harekrushna Behera、Himanshu Joshi、Manish Kumar、Aleksei Aksimentiev、Huaqiang Zeng

  DOI：10.1002/anie.202305623

  日期：2023.9.25

  Unlike many other biologically relevant ions (Na⁺, K⁺, Ca²⁺, Cl⁻, etc) and protons, whose cellular concentrations are closely regulated by highly selective channel proteins, Li⁺ ion is unusual in that its concentration is well tolerated over many orders of magnitude and that no lithium‐specific channel proteins have so far been identified. While one naturally evolved primary pathway for Li⁺ ions to traverse across the cell membrane is through sodium channels by competing with Na⁺ ions, highly sought‐after artificial lithium‐transporting channels remain a major challenge to develop. Here we show that sulfur‐containing organic nanotubes derived from intramolecularly H‐bonded helically folded aromatic foldamers of 3.6 Å in hollow cavity diameter could facilitate highly selective and efficient transmembrane transport of Li⁺ ions, with high transport selectivity factors of 15.3 and 19.9 over Na⁺ and K⁺ ions, respectively.

  摘要 与许多其他生物相关离子（Na+、K+、Ca2+、Cl- 等）和质子不同，它们的细胞浓度受到高度选择性通道蛋白的密切调节。虽然 Li+ 离子穿越细胞膜的一个自然进化的主要途径是通过钠离子通道与 Na+ 离子竞争，但备受追捧的人工锂传输通道的开发仍是一大挑战。在这里，我们展示了由中空腔直径为 3.6 Å 的分子内 H 键螺旋折叠芳香族折叠体衍生的含硫有机纳米管可促进 Li+ 离子的高选择性和高效跨膜传输，其对 Na+ 和 K+ 离子的传输选择因子分别高达 15.3 和 19.9。