4-hydroxy-8-tosyloxyquinoline

• 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: 4-hydroxy-8-tosyloxyquinoline
• 英文别名: 4-hydroxyquinolin-8-yl 4-methylbenzenesulfonate；(4-oxo-1H-quinolin-8-yl) 4-methylbenzenesulfonate
• 化学式: C₁₆H₁₃NO₄S
• 分子量: 315.35
• InChiKey: MVZNFNFZQQQQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-8-tosyloxyquinoline 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-methoxy-8-hydroxy-quinoline
  参考文献：
  名称：

  Synthesis of 4-Alkoxy-8-hydroxyquinolines

  摘要：

  Quinolines with a hydroxyl group at the 8-position and an alkoxy group at the 4-position are rare compounds. In this paper the synthesis of five 4-alkoxy-8-hydroxyquinolines is reported. The key reaction in the synthetic route is a selective protection of the hydroxyl group at C-atom 8 in 4,8-dihydroxyquinoline with a tosyl group and the hydrolytic removal of the protective group after the alkylation. The tosyl group is stable during the alkylations with various alkylating agents in the presence of sodium hydride.

  DOI：

  10.1021/jo062175i
• 作为产物：
  描述：

  4,8-二羟基喹啉-2-甲酸 在 sodium hydroxide 作用下， 以 二苯醚 、 水 、 丙酮 为溶剂， 反应 5.5h， 生成 4-hydroxy-8-tosyloxyquinoline
  参考文献：
  名称：

  Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases

  摘要：

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。

  DOI：

  10.1039/c5cc06095h

文献信息

• Synthesis of 8‐hydroxyquinolines with amino and thioalkyl functionalities at position 4
  作者：Walaa A. E. Omar、Juha P. Heiskanen、Osmo E. O. Hormi

  DOI：10.1002/jhet.5570450247

  日期：2008.3

  Six 8-hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4-hydroxy-8-tosyloxyquinoline to give 4-chloro-8-tosyloxyquinoline in 94% yield. Treatment of the 4-chloro-8-tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4-amino and 4-thioalkyl-8-hydroxyquinolines in more

  制备了在位置4具有氨基和硫代烷基官能度的六个8-羟基喹啉。合成从氯化易得的4-羟基-8-甲苯磺酰氧基喹啉开始，以94％的收率得到4-氯-8-甲苯磺酰氧基喹啉。用硫和氮亲核试剂处理4-氯-8-甲苯磺酰喹啉可以以超过70％的产率产生目标4-氨基和4-硫烷基-8-羟基喹啉。对于硫亲核试剂和吡咯烷，在位置8除去保护甲苯磺酰基的同时在位置4取代氯。
• Fused Alq3 derivatives: syntheses and photophysical characteristics
  作者：Juha P. Heiskanen、Antti E. Tolkki、Helge J. Lemmetyinen、Osmo E. O. Hormi

  DOI：10.1039/c1jm12424b

  日期：——

  Three new tetracyclic 8-hydroxyquinoline derivatives were synthesized by using a Pd catalyzed intramolecular direct arylation reaction in a key step. Furthermore, the new compounds were used as ligands in aluminium complexes and their photophysical properties were studied in detail both in solution and solid state by using absorption, steady-state, and time resolved fluorescence spectroscopies. Results show especially that the aluminium complex of 11H-indolo[3,2-c]quinolin-4-ol has the most blue-shifted emission maximum among the Alq3 derivatives to date and CIE chromaticity coordinates locate on the deep blue area (0.16, 0.12). Moreover, the fluorescence quantum yield of this compound is 3.1–3.5 times higher compared with the parent Alq3. Photophysical properties of the complex did not show major differences between the solution and the solid states. The lack of melting endotherm in DSC analysis indicates that the compound is amorphous. Based on the results, 11H-indolo[3,2-c]quinolin-4-ol has promising features to be applied as a ligand for aluminium or other metal ions in different applications.

  通过使用钯催化的分子内直接芳香化反应合成了三种新的四环8-羟基喹啉衍生物，作为关键步骤。此外，新的化合物被用作铝配合物中的配体，并通过吸收、稳态荧光和时间分辨荧光光谱技术对其光物理性质进行了详细研究。结果特别显示，11H-吲哚[3,2-c]喹啉-4-醇的铝配合物在迄今为止的Alq3衍生物中具有最蓝移的发射峰值，CIE色坐标位于深蓝区域（0.16, 0.12）。此外，该化合物的荧光量子产率比母体Alq3高出3.1-3.5倍。该配合物的光物理性质在溶液态和固态之间没有显著差异。差示扫描量热分析中没有熔融吸热峰的存在表明该化合物是非晶态的。基于这些结果，11H-吲哚[3,2-c]喹啉-4-醇在作为铝或其他金属离子的配体方面具有良好的应用前景。
• Quinolines and Oxazino-quinoline Derivatives as Small Molecule GLI1 Inhibitors Identified by Virtual Screening
  作者：Fabrizio Manetti、Luisa Maresca、Enrica Crivaro、Sara Pepe、Elena Cini、Snigdha Singh、Paolo Governa、Samuele Maramai、Giuseppe Giannini、Barbara Stecca、Elena Petricci

  DOI：10.1021/acsmedchemlett.2c00249

  日期：2022.8.11

  A virtual screening approach based on a five-feature pharmacophoric model for negative modulators of GLI1 was applied to databases of commercially available compounds. The resulting quinoline derivatives showed significant ability to reduce the GLI1 protein level and were characterized by submicromolar antiproliferative activity toward human melanoma A375 and medulloblastoma DAOY cell lines. Decoration

  基于 GLI1 负调节剂五特征药效团模型的虚拟筛选方法被应用于市售化合物的数据库。所得喹啉衍生物显示出显着降低 GLI1 蛋白水平的能力，并具有对人黑色素瘤 A375 和髓母细胞瘤 DAOY 细胞系的亚微摩尔抗增殖活性。喹啉环的修饰和恶嗪基喹啉支架的化学刚性使我们能够推断出未来配体优化的 SAR 考虑因素。
• Synthesis of 4-(2-arylvinyl)-8-hydroxyquinolines via anhydrous Heck coupling reaction and the PL properties of their Al complexes
  作者：Walaa A.E. Omar、Osmo E.O. Hormi

  DOI：10.1016/j.tet.2009.03.028

  日期：2009.5

  Anhydrous Heck coupling between 2 and eight different arylvinyl compounds using 3 mol % of PdCl2/2PPh(3) catalyst system occurs selectively at position-4 of 2 affording 4-(2-arylvinyl)-8-tosyloxyquinolines 3 in good to high yields. The tosyloxy protecting group showed high stability under anhydrous coupling conditions. Deprotection of the resulting 4-arylvinyl-8-tosyloxyquinolines produced 4-(2-arylvinyl)-8-hydroxyquinolines 4 in high yields. The aluminium complexes of the resulting 8-hydroxyquinolines have been synthesized and their photoluminescence (PL) properties have been studied. One of the complexes with a 2,4,6-trimethoxystyryl substituent at position-4 of the quinolate shows higher relative PL quantum yield than the other complexes due to the minimization of the cis-trans photo-isomerization in solution. (C) 2009 Elsevier Ltd. All rights reserved.
• HAMANA M.; KUMADAKI S., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 10, 2284-2289
  作者：HAMANA M.、 KUMADAKI S.

  DOI：——

  日期：——