5-iodo-2-methylquinolin-8-ol | 24263-95-4

• 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-iodo-2-methylquinolin-8-ol
• 英文别名: 5-Iodo-2-methyl-8-quinolinol
• CAS: 24263-95-4
• 化学式: C₁₀H₈INO
• 分子量: 285.084
• InChiKey: FAXLXQXUJQKHGO-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  383.0±42.0 °C(Predicted)
• 密度：
  1.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-iodo-2-methylquinolin-8-ol 在 盐酸 、 水 、 一氯化碘 作用下， 生成 5,7-diiodo-2-methylquinolin-8-ol
  参考文献：
  名称：

  Notes - A New Approach to Synthesis of Dihalogenated 8-Quinolinol Derivatives

  摘要：

  DOI：

  10.1021/jo01360a607
• 作为产物：
  描述：

  5,7-diiodo-2-methylquinolin-8-ol 在 吡啶 作用下， 反应 5.0h， 以92%的产率得到5-iodo-2-methylquinolin-8-ol
  参考文献：
  名称：

  Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines

  摘要：

  [GRAPHIC]A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch, ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.

  DOI：

  10.1021/jo051191x

文献信息

• Tuned Cd2+ Selectivity: Showcase of Electronic and Regio-Effect of π-Extended Di-2-Picolylamine-Substituted Quinoline-Based Tolans
  作者：Min-Sung Ko、P. Sankara Rao、Dong-Gyu Cho

  DOI：10.3390/molecules26040917

  日期：——

  π-Extended di-2-picolylamine (DPA)-substituted 8-hydroxyquinoline (8-HQ) tolans (2) were synthesized for testing electronic and regio-effects. The electron-poor CN-tolan (2b) showed clear selectivity for Cd2+ (>>Zn2+) over other metal ions via turn-on fluorescence, while the electron-rich MeO-tolan (2a) displayed no clear metal selectivity. Furthermore, considering that there was no significant energy difference between the Cd2+ complexes of 1 and 2b, the intended regio-effect (7- vs. 5-substituted effect) did not induce steric hindrance. Thus, the regio-effect is mainly electronic. Considering the above, 2a and 2b constitute a complete showcase in which electronic and regio-effects modulate the metal selectivity. The fluorescence titration of 2b (10 mM) with Cd2+ showed that the limit of detection (LOD) of the Cd2+-selective 2b was 158 nM in PBS (phosphate-buffered saline) (10 mM, pH 7.2) containing 50% MeOH.

  π-扩展的二-2-哌啶基胺（DPA）取代的8-羟基喹啉（8-HQ）托兰（2）被合成用于测试电子和区域效应。电子贫化的CN-托兰（2b）通过开启荧光清晰地选择Cd2+（>>Zn2+）而不是其他金属离子，而电子富集的MeO-托兰（2a）则没有明显的金属选择性。此外，考虑到1和2b的Cd2+配合物之间没有显著的能量差异，预期的区域效应（7- vs. 5-取代效应）不会引起立体位阻。因此，区域效应主要是电子效应。考虑到上述情况，2a和2b构成了一个完整的展示，其中电子和区域效应调节了金属选择性。2b（10 mM）与Cd2+的荧光滴定显示，Cd2+选择性的2b的检测限（LOD）在含有50％MeOH的PBS（磷酸盐缓冲液）（10 mM，pH 7.2）中为158 nM。

表征谱图