4-bromoquinolin-8-yl 4-methylbenzenesulfonate | 1166262-04-9

• 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-bromoquinolin-8-yl 4-methylbenzenesulfonate
• 英文别名: 4-bromo-8-tosyloxyquinoline；(4-Bromoquinolin-8-yl) 4-methylbenzenesulfonate；(4-bromoquinolin-8-yl) 4-methylbenzenesulfonate
• CAS: 1166262-04-9
• 化学式: C₁₆H₁₂BrNO₃S
• 分子量: 378.246
• InChiKey: JTPJTVUNJFYGNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-乙烯基吡啶 、 4-bromoquinolin-8-yl 4-methylbenzenesulfonate 在 potassium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(E)-4-(2-(pyridin-2-yl)vinyl)-8-tosyloxyquinoline
  参考文献：
  名称：

  Synthesis of 4-(2-arylvinyl)-8-hydroxyquinolines via anhydrous Heck coupling reaction and the PL properties of their Al complexes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.03.028
• 作为产物：
  描述：

  4,8-二羟基喹啉 在 sodium hydroxide 、 三溴氧磷 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 4-bromoquinolin-8-yl 4-methylbenzenesulfonate
  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

• Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases
  作者：C. C. Thinnes、A. Tumber、C. Yapp、G. Scozzafava、T. Yeh、M. C. Chan、T. A. Tran、K. Hsu、H. Tarhonskaya、L. J. Walport、S. E. Wilkins、E. D. Martinez、S. Müller、C. W. Pugh、P. J. Ratcliffe、P. E. Brennan、A. Kawamura、C. J. Schofield

  DOI：10.1039/c5cc06095h

  日期：——

  A Betti reaction was used for efficient generation of 2OG oxygenase inhibitors, including for KDM4 demethylases.

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。
• 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.