ethyl 5-amino-1-octyl-4-oxo-1, 4-dihydropyridine-3-carboxylate | 1325297-24-2

• 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: ethyl 5-amino-1-octyl-4-oxo-1, 4-dihydropyridine-3-carboxylate
• CAS: 1325297-24-2
• 化学式: C₁₆H₂₆N₂O₃
• 分子量: 294.394
• InChiKey: YQECJFACGXWTBY-UHFFFAOYSA-N

物化性质

• 沸点：
  410.4±45.0 °C(predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-1-octyl-4-oxo-1, 4-dihydropyridine-3-carboxylate 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 C₇₀H₁₀₀N₁₀O₁₀
  参考文献：
  名称：

  BOP介导的C5对称大环吡啶酮五聚体的一锅合成。

  摘要：

  我们在这里首次报告由内部放置的分子内H键促进和引导的BOP介导的一锅大环化，以允许高度选择性地形成五残基阳离子结合大环。

  DOI：

  10.1039/c1cc14377h
• 作为产物：
  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

文献信息

• One-Pot Synthesis of Strained Macrocyclic Pyridone Hexamers and Their High Selectivity toward Cu²⁺ Recognition
  作者：Changliang Ren、Jie Shen、Huaqiang Zeng

  DOI：10.1021/acs.orglett.5b02780

  日期：2015.12.18

  The removal of Cu2+ ions is relevant to environmental pollution control and neurodegenerative disease treatment. A novel family of strained macrocyclic pyridone hexamers, which exhibit highly selective recognition of Cu2+ ions and reduce copper content in artificial seawater by 97% at a very low [host]:[CuCl2] molar ratio of 2:1, is documented.

  Cu 2+离子的去除与环境污染控制和神经退行性疾病的治疗有关。记录了一个新的应变大环吡啶酮六聚体家族，该化合物在非常低的[主体]：[CuCl 2 ]摩尔比为2：1的情况下显示出对Cu 2+离子的高度选择性识别，并将人造海水中的铜含量降低了97％。
• Surprisingly High Selectivity and High Affinity in Mercury Recognition by H-Bonded Cavity-Containing Aromatic Foldarands
  作者：Jie Shen、Changliang Ren、Huaqiang Zeng

  DOI：10.1021/jacs.6b13342

  日期：2017.4.19

  well over 22 other metal ions. Despite the lack of sulfur atoms and having only oxygen-donor atoms in its structure, the best foldarand molecule, i.e., tetramer 4, exhibits a selectivity factor of at least 19 in differentiating the most tightly bound Hg2+ ion from all other metal ions, and a binding capacity that is ≥18 times that of thio-crown ethers. These two noteworthy binding characters make possible

  在没有大环限制的情况下，很少有合成系统具有主要与溶剂无关的折叠构象，易于对金属离子进行高选择性和高亲和力识别。我们在这里报告了这样一类独特的构象鲁棒性模块化可调折叠分子，称为折叠分子，它可以识别 Hg2+ 离子，比其他 22 种金属离子出奇地好。尽管缺乏硫原子并且其结构中只有氧供体原子，但最好的折叠分子，即四聚体 4，在区分最紧密结合的 Hg2+ 离子与所有其他金属离子方面表现出至少 19 的选择性因子，并且结合能力≥硫冠醚的18倍。这两个值得注意的结合特征使 Hg2+ 离子的低水平去除成为可能。随着 [4]：[Hg2+] 摩尔比为 5:1 和单相双相溶剂萃取，纯水中的 Hg2+ 离子浓度可大幅降低 98%（从 200 到 4 ppb）。4 还可以通过多次连续提取将人工地下水中的汞含量高效降低 98%（从 500 到 10 ppb），总消耗量为 4，即 [4]:[Hg2+] 摩尔比为 9:1
• Intramolecularly Hydrogen-Bonded Aromatic Pentamers as Modularly Tunable Macrocyclic Receptors for Selective Recognition of Metal Ions
  作者：Ying Liu、Jie Shen、Chang Sun、Changliang Ren、Huaqiang Zeng

  DOI：10.1021/jacs.5b07123

  日期：2015.9.23

  Despite the tremendous progress that has been made in macrocyclic chemistry since the discovery of corands, cryptands, and spherands more than four decades ago, macrocyclic systems possessing a high level of controllability in structural configuration concurrent with a systematic tunability in function are still very rare. Employing an inner design strategy to orient Hbonding forces toward a macrocyclic cavity interior while convergently aligning exchangeable ionbinding building blocks that dictate a near-identical backbone curvature, we demonstrate here a novel pentagonal framework that not only enables its variable interior cavity to be maintained at near-planarity but also allows its ion-binding potential to be highly tunable. The H-bonded macrocyclic pentamers thus produced have allowed a systematic and combinatorial evolution of ion-selective pentamers for preferential recognition of Cs+, K+, or Ag+ ions.