3-benzyloxy-5-(dimethylaminomethyl)-2-methyl-4(1H)-pyridinone | 174095-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxy-5-(dimethylaminomethyl)-2-methyl-4(1H)-pyridinone
• 英文别名: 5-[(dimethylamino)methyl]-2-methyl-3-phenylmethoxy-1H-pyridin-4-one
• CAS: 174095-91-1
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: MGGSQVKUSTWCSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-5-(dimethylaminomethyl)-2-methyl-4(1H)-pyridinone 在 palladium dihydroxide 环己烯 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以87%的产率得到2,5-dimethyl-3-hydroxy-4(1H)-pyridinone
  参考文献：
  名称：

  3-羟基-2（1H）-吡啶酮和3-羟基-4（1H）-吡啶酮的定向氨甲基化：异-去铁酮的合成

  摘要：

  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。

  DOI：

  10.1016/0040-4020(95)01016-5
• 作为产物：
  描述：

  3-(苄氧基)-2-甲基-4H-吡喃-4-酮 在 ammonium hydroxide 、 聚合甲醛 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-benzyloxy-5-(dimethylaminomethyl)-2-methyl-4(1H)-pyridinone
  参考文献：
  名称：

  Prediction of 3-hydroxypyridin-4-one (HPO) log K1 values for Fe(iii)

  摘要：

  为了帮助设计用于治疗的三羟基吡啶-4-酮（HPOs）作为Fe3+螯合剂，开发了一种新方法，利用量子力学（QM）计算预测化合物的铁结合亲和力（更具体地说，是它们的log K1值）。报告/测量的HPO log K1值通过与相应化合物配位基团pKa值和的总和的相关性得到验证。使用已知log K1值的十一种HPO作为训练集，通过采用B3LYP/6-31+G(d)/CPCM模型化学（以Bondi半径和水作为溶剂）进行QM计算，显示可以获得可靠的预测。使用这种方法，观察到的训练集化合物的log K1值与预测值紧密匹配，观察值与预测值之间的相关性为r2 = 0.9。随后，使用该方法对42种已知log K1值的HPO的预测值在±0.32 log单位内是准确的。为了进一步研究该方法的预测能力，合成了四种新型HPO，并对其log K1值进行了实验测定。将这些预测的log K1值与测量值进行比较，得到的绝对偏差为0.22（13.87对14.09）、0.02（14.31对14.29）、0.12（14.62对14.50）和0.13（15.04对15.17）。此处报告的预测方法是首个在没有pKa值的情况下预测铁螯合剂绝对log K1值的方法。

  DOI：

  10.1039/c2dt31254a

文献信息

• Utilization of Self-Sorting Processes To Generate Dynamic Combinatorial Libraries with New Network Topologies
  作者：Isabelle Saur、Rosario Scopelliti、Kay Severin

  DOI：10.1002/chem.200500621

  日期：2006.1.23

  give dynamic combinatorial libraries. In combination with structurally related complexes based on amino-methylated 3-hydroxy-2-(1H)-pyridone ligands, an exchange of metal fragments but no mixing of ligands was observed. This self-sorting behavior was used to construct dynamic combinatorial libraries of macrocycles, in which two four-component sub-libraries are connected by two common building blocks

  描述了水溶性有机金属大环的合成。它们是通过在半三明治复合物[[Ru（C6H5Me）Cl2] 2]，[[Ru（对-cymene）Cl2] 2]，[[Rh（Cp）Cl2] 2]，和[[Ir（Cp *）Cl2] 2]与配体5-二甲基氨基甲基-3-羟基-2-甲基-4-（1H）-吡啶酮在pH值为8的缓冲水溶液中。通过单晶X射线晶体学测定β-cymene）配合物。混合后，这些复合物发生加扰反应，得到动态组合库。与基于氨基甲基化的3-羟基-2-（1H）-吡啶酮配体的结构相关的配合物相结合，观察到金属碎片的交换，但未观察到配体的混合。这种自排序行为被用来构建动态的大循环组合库，其中两个四个组成部分的子库通过两个常见的构建基块进行连接。这种类型的网络拓扑会影响库的自适应行为，如以锂离子为目标的选择实验所证明的那样。
• Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives
  作者：Afshin Fassihi、Daryoush Abedi、Lotfollah Saghaie、Razieh Sabet、Hossein Fazeli、Ghasem Bostaki、Omid Deilami、Hekmatollah Sadinpour

  DOI：10.1016/j.ejmech.2008.10.022

  日期：2009.5

  A series of Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones, namely 2-alkyl-3-hydroxy-5-N-piperidylmethyl or N,N-dialkylaminomethyl pyridine-4-ones 9, 10 and 15-18, two derivatives of N-aryl-2methyl-3-hydroxy-pyridine-4-ones 19, 20 and two N-alkyl derivatives of maltol, 21 and 22 were prepared. They were screened for their antibacterial and antifungal activities against a variety of microorganisms using micro plate Alamar Blues assay (MABA) method. Multiple linear regressions (MLR) analysis was performed for the synthesized compounds as well as a series of pyridinone and pyranone derivatives 23-43 which have been synthesized and evaluated for antimicrobial activity by other researchers previously. Studied compounds showed a better quantitative structure-activity relationship (QSAR) model for the antimicrobial activity against Candida albicans and Staphylococcus aureus in comparison with other tested microorganisms. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis of 5-benzyloxy-1,4-dihydro-6-methyl-4-oxopyridine-3-carbaldehyde by aerobic oxidation of the 5-dimethylaminomethyl analogue: optimisation of the reaction conditions
  作者：Yong Min Ma、Robert C Hider

  DOI：10.1016/j.tetlet.2010.01.027

  日期：2010.3

  A successful introduction of the formyl group at position 5 of 3-hydroxypyridin-4-one was achieved by aerobic oxidation, catalysed by NHS/Co(II). To obtain a practical yield, the reaction conditions were optimised. (C) 2010 Elsevier Ltd. All rights reserved.
• 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。
• Prediction of 3-hydroxypyridin-4-one (HPO) log K1 values for Fe(iii)
  作者：Yu-Lin Chen、Dave J. Barlow、Xiao-Le Kong、Yong-Min Ma、Robert C. Hider

  DOI：10.1039/c2dt31254a

  日期：——

  As a means to aid in the design of 3-hydroxypyridin-4-ones (HPOs) intended for use as therapeutic Fe3+ chelating agents, a novel methodology has been developed using quantum mechanical (QM) calculations for predicting the iron binding affinities of the compounds (more specifically, their log K1 values). The reported/measured HPO log K1 values were verified through their correlation with the corresponding sum of the compounds’ ligating group pKa values. Using a training set of eleven HPOs with known log K1 values, reliable predictions are shown to be obtained with QM calculations using the B3LYP/6-31+G(d)/CPCM model chemistry (with Bondi radii, and water as solvent). With this methodology, the observed log K1 values for the training set compounds are closely matched by the predicted values, with the correlation between the observed and predicted values giving r2 = 0.9. Predictions subsequently made by this method for a test set of 42 HPOs of known log K1 values gave predicted values accurate to within ±0.32 log units. In order to further investigate the predictive power of the method, four novel HPOs were synthesised and their log K1 values were determined experimentally. Comparison of these predicted log K1 values against the measured values gave absolute deviations of 0.22 (13.87 vs. 14.09), 0.02 (14.31 vs. 14.29), 0.12 (14.62 vs. 14.50), and 0.13 (15.04 vs. 15.17). The prediction methodology reported here is the first to be provided for predicting the absolute log K1 values of iron-chelating agents in the absence of pKa values.

  为了帮助设计用于治疗的三羟基吡啶-4-酮（HPOs）作为Fe3+螯合剂，开发了一种新方法，利用量子力学（QM）计算预测化合物的铁结合亲和力（更具体地说，是它们的log K1值）。报告/测量的HPO log K1值通过与相应化合物配位基团pKa值和的总和的相关性得到验证。使用已知log K1值的十一种HPO作为训练集，通过采用B3LYP/6-31+G(d)/CPCM模型化学（以Bondi半径和水作为溶剂）进行QM计算，显示可以获得可靠的预测。使用这种方法，观察到的训练集化合物的log K1值与预测值紧密匹配，观察值与预测值之间的相关性为r2 = 0.9。随后，使用该方法对42种已知log K1值的HPO的预测值在±0.32 log单位内是准确的。为了进一步研究该方法的预测能力，合成了四种新型HPO，并对其log K1值进行了实验测定。将这些预测的log K1值与测量值进行比较，得到的绝对偏差为0.22（13.87对14.09）、0.02（14.31对14.29）、0.12（14.62对14.50）和0.13（15.04对15.17）。此处报告的预测方法是首个在没有pKa值的情况下预测铁螯合剂绝对log K1值的方法。