4-o-methylphenyl-8-tosyloxyquinoline | 1108187-58-1

• 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-o-methylphenyl-8-tosyloxyquinoline
• 英文别名: [4-(2-Methylphenyl)quinolin-8-yl] 4-methylbenzenesulfonate；[4-(2-methylphenyl)quinolin-8-yl] 4-methylbenzenesulfonate
• CAS: 1108187-58-1
• 化学式: C₂₃H₁₉NO₃S
• 分子量: 389.475
• InChiKey: NFPBILVYYNFFBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  4-o-methylphenyl-8-tosyloxyquinoline 在 sodium hydroxide 、 水 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.0h， 以99%的产率得到4-o-methylphenyl-8-hydroxyquinoline
  参考文献：
  名称：

  4-Aryl-8-hydroxyquinolines from 4-chloro-8-tosyloxyquinoline using a Suzuki–Miyaura cross-coupling approach

  摘要：

  4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki-Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydrous Suzuki-Miyaura reaction conditions allows the use of commercially available but relative inert 5-chloro-8-hydroxyquinoline for the synthesis of 5-phenyl-8-hydroxyquinoline. Deprotection could easily be made by using suitable nucleophiles to afford the final 5-phenyl and 4-aryl-8-hydroxyquinolines in high yields. Under acidic conditions the tosyloxy group is sufficiently stable to allow selective further modification of acid labile functional groups. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.097
• 作为产物：
  描述：

  (4-chloroquinolin-8-yl)-4-methylbenzenesulfonate 、 2-甲基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以89%的产率得到4-o-methylphenyl-8-tosyloxyquinoline
  参考文献：
  名称：

  4-Aryl-8-hydroxyquinolines from 4-chloro-8-tosyloxyquinoline using a Suzuki–Miyaura cross-coupling approach

  摘要：

  4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki-Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydrous Suzuki-Miyaura reaction conditions allows the use of commercially available but relative inert 5-chloro-8-hydroxyquinoline for the synthesis of 5-phenyl-8-hydroxyquinoline. Deprotection could easily be made by using suitable nucleophiles to afford the final 5-phenyl and 4-aryl-8-hydroxyquinolines in high yields. Under acidic conditions the tosyloxy group is sufficiently stable to allow selective further modification of acid labile functional groups. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.097

文献信息

• 4-Aryl-8-hydroxyquinolines from 4-chloro-8-tosyloxyquinoline using a Suzuki–Miyaura cross-coupling approach
  作者：Juha P. Heiskanen、Osmo E.O. Hormi

  DOI：10.1016/j.tet.2008.10.097

  日期：2009.1

  4-Chloro-8-tosyloxyquinoline was successfully cross-coupled with various arylboronic acids in anhydrous Suzuki-Miyaura conditions. The protective tosyl group was stable during the anhydrous coupling. The use of tosyl protection in association with anhydrous Suzuki-Miyaura reaction conditions allows the use of commercially available but relative inert 5-chloro-8-hydroxyquinoline for the synthesis of 5-phenyl-8-hydroxyquinoline. Deprotection could easily be made by using suitable nucleophiles to afford the final 5-phenyl and 4-aryl-8-hydroxyquinolines in high yields. Under acidic conditions the tosyloxy group is sufficiently stable to allow selective further modification of acid labile functional groups. (C) 2008 Elsevier Ltd. All rights reserved.