8-(3,5-dimethoxybenzyl)quinoline | 1332874-75-5

• 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: 8-(3,5-dimethoxybenzyl)quinoline
• CAS: 1332874-75-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: SYJBLULPSVWFOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.35
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  间苯二酚 、 [Pd(κ2-N,C-2-8-methylquinoline)(OAc)]2 在 溶剂黄146 、 二甲基亚砜 、 对苯醌 作用下， 反应 15.0h， 生成 8-(3,5-dimethoxybenzyl)quinoline 、 8-(2,4-dimethoxybenzyl)quinoline
  参考文献：
  名称：

  Controlling Site Selectivity in Pd-Catalyzed Oxidative Cross-Coupling Reactions

  摘要：

  This paper presents a detailed investigation of the factors controlling site selectivity in the Pd-mediated oxidative coupling of 1,3-disubstituted and 1,2,3-trisubstituted arenes (aryl -H) with cyclometalating substrates (L similar to C-H). The influence of both the concentration and the steric/electronic properties of the quinone promoter are studied in detail. In addition, the effect of steric/electronic modulation of the carboxylate ligand is discussed. Finally, we demonstrate that substitution of the carboxylate for a carbonate X-type ligand leads to a complete reversal in site selectivity for many arene substrates. The origins of these trends in site selectivity are discussed in the context of the mechanism of Pd-catalyzed oxidative cross-coupling.

  DOI：

  10.1021/ja1097918