3-hydroxy-4-piperidino-methyl-2(1H)-pyridinone | 153112-29-9

• 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: 3-hydroxy-4-piperidino-methyl-2(1H)-pyridinone
• 英文别名: 3-hydroxy-4-piperidino-methyl-2-(1H)-pyridone；4-piperidinomethyl-3-hydroxy-2(1H)-pyridinone；2(1H)-Pyridinone, 3-hydroxy-4-(1-piperidinylmethyl)-；3-hydroxy-4-(piperidin-1-ylmethyl)-1H-pyridin-2-one
• CAS: 153112-29-9
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: BFECZMZYJKKZTA-UHFFFAOYSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [RuCl2(benzene)]2 、 3-hydroxy-4-piperidino-methyl-2(1H)-pyridinone 在 phosphate buffer 作用下， 以 重水 为溶剂， 生成 [Ru(C6H6)(2,3-oxy-4-piperidino-methyl-pyridine(1H+))]3Cl12
  参考文献：
  名称：

  使用自组装离子载体在中性 pH 条件下选择性络合水中的 Li+

  摘要：

  三核金属大环是通过在中性 pH 值的水中组装三齿配体和钌配合物而获得的。该配合物作为锂离子的有效离子载体，Li+/Na+ 选择性为 10 000:1。

  DOI：

  10.1021/ja036621k
• 作为产物：
  描述：

  聚合甲醛 、 哌啶 、 吡啶-2,3-二醇 以 乙醇 、 水 为溶剂， 反应 12.5h， 以92.5%的产率得到3-hydroxy-4-piperidino-methyl-2(1H)-pyridinone
  参考文献：
  名称：

  Synthesis of 4,5,6-trisubstituted 2,3-pyridinediones via Mannich reaction and oxidation–Michael addition of 3-hydroxy-2(1H)-pyridinones

  摘要：

  4-取代的3-羟基-2(1H)-吡啶酮2是通过3-羟基-2(1H)-吡啶酮与仲胺和甲醛的曼尼希反应制备的。然后，分离的产物在 NaIO3 作为氧化剂存在下通过氧化-迈克尔加成反应与芳香胺反应，以良好的收率 (80.2–88.9%) 生成 4,5,6-三取代-2,3-吡啶二酮 3。通过1H NMR、ESI-MS、IR和元素分析对产物结构进行了表征。

  DOI：

  10.1007/s11164-012-0495-z

文献信息

• Directed aminomethylation of 3-hydroxy-2(1H)-pyridinones and 3-hydroxy-4(1H)-pyridinones: Synthesis of iso-deferiprone
  作者：Manojbhai K. Patel、Raymond Fox、Paul D. Taylor

  DOI：10.1016/0040-4020(95)01016-5

  日期：1996.1

  aminomethylation of N-unsubstituted 3-hydroxy-2-(1H)-pyridinones and 3-hydroxy-4(1H)-pyridinones, under Mannich reaction conditions, is directed by the hydroxyl group when this is unprotected and by the kelo group when the hydroxyl is protected as an ether. This offers a convenient route to a variety of Mannich base synthons useful in the synthesis of derivatives of these clinically important, bidentate

  在曼尼希反应条件下，N-未取代的3-羟基-2-（1H）-吡啶酮和3-羟基-4（1H）-吡啶酮的氨基甲基化位点由未保护的羟基和开环组成当羟基被保护为醚时的基团。这提供了通往各种曼尼希碱基合成子的便捷途径，这些合成子可用于合成这些临床上重要的双齿金属离子螯合剂的衍生物。这可以通过3-羟基-2-（1H）-吡啶酮，3-甲氧基-2（1H）-吡啶酮，2-羟基甲基-5-羟基-4（1H）吡啶酮和3-苄氧基-2-甲基的反应来举例说明。-4（1H）-吡啶酮。
• pH-Triggered Assembly of Organometallic Receptors for Lithium Ions
  作者：Zacharias Grote、Rosario Scopelliti、Kay Severin

  DOI：10.1021/ja044874n

  日期：2004.12.1

  The reaction of half-sandwich complexes of ruthenium, rhodium, and iridium with amino-substituted 3-hydroxy-2-pyridone ligands in aqueous solution gives monomeric O,O'-chelate complexes. Upon addition of base, the complexes assemble to form trimeric metallamacrocycles, as evidenced by NMR spectroscopy and single-crystal X-ray analyses. The macrocycles are able to act as highly selective receptors for lithium ions. The binding constants depend on the nature of the half-sandwich complex. the ligand, and the pH. With a commercially available (cymene)Ru complex, a receptor with a Li-divided by binding Constant of K-a = 5.8 (+/-1.0) x 10(4) M-1 and a Li-divided by-Na+ selectivity of 10 000:1 can be obtained. The fact that the assembly process of the receptor is pH-dependent can be used to detect the presence of lithium ions by a pH measurement. Furthermore, it is possible to transduce the binding of Li-divided by into a change of color by means of a chemical reaction with FeCl3. This allows the detection of Li-divided by in the pharmacologically relevant concentration range of 0.5-1.5 mM by the "naked eye".
• Organometallic complexes that interconvert between trimeric and monomeric structures as a function of pH and their effect on human cancer and fibroblast cells
  作者：Wee Han Ang、Zacharias Grote、Rosario Scopelliti、Lucienne Juillerat-Jeanneret、Kay Severin、Paul J. Dyson

  DOI：10.1016/j.jorganchem.2008.11.026

  日期：2009.3

  Organometallic half-sandwich complexes based on ruthenium with aminomethyl-substituted 3-hydroxy-2-pyridone ligands exist in aqueous solution as monomeric O,O'-chelate complexes or trimeric metallamacrocycles depending upon the pH. We hypothesized that administration of the compounds as stable trimers, which subsequently convert to active monomers at the reduced pH of the cancer environment, could facilitate their delivery to cancer cells without undergoing deactivation. Thus, the compounds were evaluated against cancer and fibroblast cell lines in vitro. A series of rhodium complexes, which exist mainly as monomers at neutral pH, were also studied for comparative purposes. (c) 2008 Elsevier B.V. All rights reserved.
• 1H and 13C NMR spectral studies of some Mannich bases. Revised structures for the mono-substituted products from 3-hydroxy-2-pyridone
  作者：Alan G. Osborne、Lee Jackson、Paul D. Taylor

  DOI：10.1016/0584-8539(93)80237-5

  日期：1993.11

  H-1 and C-13 chemical shifts and J(HH) and J(CH) coupling constants are reported for a series of mono-Mannich bases derived from 3-hydroxy-2-pyridone. These compounds should be regarded as the 4-isomers rather than the 6-isomers proposed previously.