methyl 2-(quinolin-8-yloxy)acetate | 63333-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(quinolin-8-yloxy)acetate
• 英文别名: methyl (8-quinolyloxy)acetate；Methyl (quinolin-8-yloxy)acetate；methyl 2-quinolin-8-yloxyacetate
• CAS: 63333-80-2
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD01202514
• 分子量: 217.224
• InChiKey: QQOCGTSZDWOXJH-UHFFFAOYSA-N

物化性质

• 沸点：
  350.2±17.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(quinolin-8-yloxy)acetate 以 甲醇 、 乙醇 为溶剂， 反应 54.0h， 生成 N-(2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)-2-(quinolin-8-yloxy)acetamide
  参考文献：
  名称：

  基于1,8-萘二甲酰亚胺和8-羟基喹啉的新型金属离子荧光化学传感器

  摘要：

  合成了一种基于1,8-萘二甲酰亚胺和8-羟基喹啉的新型荧光化学传感器，并在不同金属阳离子（Hg 2 +，Ag +，Zn 2 +，Fe 2 +，Cd 2 +，Pb研究了2+，Ca 2 +，Cu 2 +，Mg 2+和Ba 2+）。它显示出一些重金属和过渡金属（HTM）离子的荧光猝灭，并且猝灭强烈取决于HTM离子的性质。

  DOI：

  10.1002/cjoc.201180375
• 作为产物：
  描述：

  8-羟基喹啉 在 4-二甲氨基吡啶 、 potassium iodide 、 sodium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 methyl 2-(quinolin-8-yloxy)acetate
  参考文献：
  名称：

  基于1,8-萘二甲酰亚胺和8-羟基喹啉的新型金属离子荧光化学传感器

  摘要：

  合成了一种基于1,8-萘二甲酰亚胺和8-羟基喹啉的新型荧光化学传感器，并在不同金属阳离子（Hg 2 +，Ag +，Zn 2 +，Fe 2 +，Cd 2 +，Pb研究了2+，Ca 2 +，Cu 2 +，Mg 2+和Ba 2+）。它显示出一些重金属和过渡金属（HTM）离子的荧光猝灭，并且猝灭强烈取决于HTM离子的性质。

  DOI：

  10.1002/cjoc.201180375

文献信息

• New<i>N</i>-(Aryl)-5-((quinolin-8-yloxy)methyl)-1,3,4-oxa/Thiadiazol-2-amines and 4-Aryl-5-((quinolin-8-yloxy)methyl)-2<i>H</i>-1,2,4-triazole-3(4<i>H</i>)-thiones, Synthesis and Characterization
  作者：Aamer Saeed、Naeem Abbas、Aliya Ibrar、Michael Bolte

  DOI：10.1002/jhet.1817

  日期：2014.9

  intramolecular cyclization led to N‐(aryl)‐5‐((quinolin‐8‐yloxy)methyl)‐1,3,4‐oxa/thiadiazol‐2‐amines (5a, 5b, 5c, 5d, 5e, 5f, 5g) and 4‐aryl‐5‐((quinolin‐8‐yloxy)methyl)‐2H‐1,2,4‐triazole‐3(4H)‐thiones (6a, 6b, 6c, 6d, 6e, 6f, 6g), respectively. All the synthesized compounds were characterized by spectroscopic techniques and elemental analyses. The thiosemicarbazide (4c) was also confirmed by X‐ray crystallography

  在这项研究中，将8-羟基喹啉（1）与氯乙酸甲酯反应得到的2-甲基（喹啉-8-基氧基）乙酸甲酯（2）与水合肼缩合，得到碳酰肼（3）。通过用取代的苯基异/硫代异氰酸酯处理3，获得硫代/氨基脲化合物（4a，4b，4c，4d，4e，4f，4g）。在图4a，图4b，图4c，图4d，图4e，4f中，4克酸性和碱性分子内环化反应导致N-（芳基）-5-（（喹啉-8-基氧基）甲基）-1,3,4-氧杂/噻二唑-2-胺（5a，5b，5c，5d，5e，5f，5g）和4-芳基-5-（（（喹啉-8氧基）甲基）-2 H -1,2,4-三唑-3（4 H）-硫酮（6a，6b，6c，6d，6e，6f，6g）。所有合成的化合物都通过光谱技术和元素分析进行​​了表征。硫代氨基脲（X射线晶体学也证实了4c）。
• Anion recognition by a family of quinoline-functionalised bis-amide hosts in solid state and in solution
  作者：Subrata Jana、Amanda L. Whiting、Anita Hazra、Saikat Sen、Shyamaprosad Goswami、Goverdhan Mehta、Hoong-Kun Fun、Fraser Hof

  DOI：10.1080/10610278.2012.676179

  日期：2012.6.1

  8-oxyquinoline receptors and coordinating anions is investigated. Anion recognition properties and conformations were studied by solid-state structures, Hartree–Fock calculations and solution-phase 1H NMR investigations. Our findings suggest that the amide-oxyquinoline motif coordinates anions and water with a well-defined, consistent geometry involving multiple hydrogen bonds. Solution studies of the neutral

  研究了一系列双齿、酰胺功能化的 8-羟基喹啉受体与配位阴离子之间的相互作用。通过固态结构、Hartree-Fock 计算和溶液相 1H NMR 研究来研究阴离子识别特性和构象。我们的研究结果表明，酰胺-羟基喹啉基序以包含多个氢键的明确、一致的几何结构协调阴离子和水。中性受体的溶液研究表明，尽管无法通过氢键直接参与，但未质子化的羟喹啉环间接促进了相邻酰胺 NH 基团的阴离子结合。
• Interactions of amino acids, carboxylic acids, and mineral acids with different quinoline derivatives
  作者：Dipjyoti Kalita、Himangshu Deka、Shyam Sundar Samanta、Subrata Guchait、Jubaraj B. Baruah

  DOI：10.1016/j.molstruc.2011.01.040

  日期：2011.3

  A series of quinoline containing receptors having amide and ester bonds are synthesized and characterised. The relative binding abilities of these receptors with various amino acids, carboxylic acids and mineral acids are determined by monitoring the changes in fluorescence intensity. Among the receptors bis(2-(quinolin-8-yloxy)ethyl) isophthalate shows fluorescence enhancement on addition of amino acids whereas the other receptors shows fluorescence quenching on addition of amino acids. The receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy) propanamide has higher binding affinity for amino acids. However, the receptor N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide having similar structure do not bind to amino acids. This is attributed to the concave structure of the former which is favoured due to the presence of methyl substituent. The receptor bis(2-(quinolin-8-yloxy)ethyl) isophthalate do not bind to hydroxy carboxylic acids, but is a good receptor for dicarboxylic acids. The crystal structure of bromide and perchlorate salts of receptor 2-bromo-N-(quinolin-8-yl)-propanamide are determined. In both the cases the amide groups are not in the plane of quinoline ring. The structure of N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide, N-(2-methoxyphenethyl)-2-(quinolin-8-yloxy)acetamide and their salts with maleic acid as well as fumaric acid are determined. It is observed that the solid state structures are governed by the double bond geometry of these two acid. Maleic acid forms salt in both the cases, whereas fumaric acid forms either salt or co-crystals. (C) 2011 Elsevier B.V. All rights reserved.