5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline | 1245934-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline
• 英文别名: Methyl 3-[(8-hydroxyquinolin-5-yl)methoxy]-2,2-dimethylpropanoate
• CAS: 1245934-94-4
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: ZMYNDTLEBHZGMW-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline 、 二氮杂18-冠醚-6 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以86%的产率得到N,N'-bis((5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether
  参考文献：
  名称：

  Microwave Assisted Synthesis of a Small Library of SubstitutedN,N′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 Ethers

  摘要：

  N,N'- Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.

  DOI：

  10.1021/jo101173t
• 作为产物：
  描述：

  羟基三甲基乙酸甲酯 、 5-(氯甲基)-8-羟基喹啉盐酸盐 在 ammonium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以85%的产率得到5-(2-carbomethoxy-2-methyl)propyloxymethyl-8-hydroxy-7-quinoline
  参考文献：
  名称：

  Microwave Assisted Synthesis of a Small Library of SubstitutedN,N′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 Ethers

  摘要：

  N,N'- Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.

  DOI：

  10.1021/jo101173t

文献信息

• [EN] PROCEDURE FOR THE SYNTHESIS OF FLUORESCENT PROBES FOR METALS<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE SONDES FLUORESCENTES POUR MÉTAUX
  申请人：UNIV BOLOGNA ALMA MATER

  公开号：WO2011077226A1

  公开（公告）日：2011-06-30

  A synthesis procedure is provided of a compound having general formula III, in which m and m' are selected, independently of each other, from a group consisting of : 1, 2, 3; the procedure comprises a synthetic step, during which a crown compound presenting the general formula I reacts with a derivative of a 8-hydroxy-quinoline (Der-H) in the presence of an aldehyde II.(I, II, III).
• Microwave Assisted Synthesis of a Small Library of Substituted<i>N</i>,<i>N</i>′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 Ethers
  作者：Giovanna Farruggia、Stefano Iotti、Marco Lombardo、Chiara Marraccini、Diego Petruzziello、Luca Prodi、Massimo Sgarzi、Claudio Trombini、Nelsi Zaccheroni

  DOI：10.1021/jo101173t

  日期：2010.9.17

  N,N'- Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.