ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate | 1402606-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate
• 英文别名: ethyl [3-(benzyloxy)-2-oxopyridin-1(2H)-yl]acetate；Ethyl 2-(2-oxo-3-phenylmethoxypyridin-1-yl)acetate
• CAS: 1402606-45-4
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: ZAFWTYXGZJAKBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate 在 硼烷 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.0h， 生成 3-(benzyloxy)-1-(2-chloroethyl)-1H-pyridin-2-one
  参考文献：
  名称：

  A Practical Route for the Preparation of 1,4,7-Triazacyclononanyl Diacetates with a Hydroxypyridinonate Pendant Arm

  摘要：

  报告了三氮四环羟基吡啶酮（HOPO-TACN）衍生物的制备，作为潜在的生物医学应用金属螯合剂。合成基于一种汇聚合成方法，其中关键中间体二叔丁基-2,2′-(1,4,7-三氮烷-1,4-二基)二乙酸酯与羟基吡啶酮侧链相偶联。该方法适用于快速合成具有生物医学意义的金属螯合剂HOPO-TACN。

  DOI：

  10.3390/molecules201019393
• 作为产物：
  描述：

  吡啶-2,3-二醇 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 76.0h， 生成 ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate
  参考文献：
  名称：

  A Practical Route for the Preparation of 1,4,7-Triazacyclononanyl Diacetates with a Hydroxypyridinonate Pendant Arm

  摘要：

  报告了三氮四环羟基吡啶酮（HOPO-TACN）衍生物的制备，作为潜在的生物医学应用金属螯合剂。合成基于一种汇聚合成方法，其中关键中间体二叔丁基-2,2′-(1,4,7-三氮烷-1,4-二基)二乙酸酯与羟基吡啶酮侧链相偶联。该方法适用于快速合成具有生物医学意义的金属螯合剂HOPO-TACN。

  DOI：

  10.3390/molecules201019393

文献信息

• Organometallic Ruthenium and Osmium Compounds of Pyridin‐2‐ and ‐4‐ones as Potential Anticancer Agents
  作者：Helena Henke、Wolfgang Kandioller、Muhammad Hanif、Bernhard K. Keppler、Christian G. Hartinger

  DOI：10.1002/cbdv.201200005

  日期：2012.9

  Organometallic RuII compounds are among the most widely studied anticancer agents. Functionalizing metal centers with biomolecule‐derived ligands has been shown to be a promising strategy to improve the antiproliferative activity of metal‐based chemotherapeutics. Herein, the synthesis of a series of novel 3‐hydroxypyridin‐2‐one‐derived ligands and their MII(η6‐p‐cymene) half‐sandwich complexes (M=Ru

  有机金属 RuII 化合物是研究最广泛的抗癌剂之一。用生物分子衍生的配体功能化金属中心已被证明是提高金属基化疗药物抗增殖活性的一种有前景的策略。本文描述了一系列新型 3-羟基吡啶-2-one 衍生配体及其 MII(η6-p-cymene) 半夹心配合物 (M=Ru, Os) 的合成。通过1D-和2D-NMR光谱以及元素分析对化合物进行表征。
• Preparation of 3-benzyloxy-2-pyridinone functional linkers: tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators
  作者：Sarah Gibson、Rasika Fernando、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tet.2015.10.031

  日期：2015.12

  In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2, undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcohols was found to be of limited value due to competing O-alkylation that led to product mixtures. The phthalimide 3j can be converted in two steps to HOPO isocyanate 6 in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcohols in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10, an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an additional hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 and 19, based on the structure of desferrioxamine, a well-known trihydroxamate siderophore. (C) 2015 Elsevier Ltd. All rights reserved.
• HIDER, R. C.;KONTOGHIORGHES, G.;SILVER, J.;STOCKHAM, M. A.
  作者：HIDER, R. C.、KONTOGHIORGHES, G.、SILVER, J.、STOCKHAM, M. A.

  DOI：——

  日期：——