4-bromo-2-(2-phenylethyl)quinoline

• 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-bromo-2-(2-phenylethyl)quinoline
• 化学式: C₁₇H₁₄BrN
• 分子量: 312.209
• InChiKey: BCJCWIBXTRVSRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,4-二溴喹啉 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium diazodicarboxylate 、 溶剂黄146 、 二异丙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 47.0h， 生成 4-bromo-2-(2-phenylethyl)quinoline
  参考文献：
  名称：

  Regioselective Sonogashira Couplings of 2,4-Dibromoquinolines. A Correction

  摘要：

  Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.

  DOI：

  10.1021/jo034122w

文献信息

• Solvent-Free Mechanoradical-Mediated Minisci-Type C–H Alkylation of N-Heteroarenes
  作者：Xiang Gu、Taoyong Wang、KaKing Yan

  DOI：10.1021/acs.orglett.3c02480

  日期：2023.10.13

  mechanochemistry is described. Under solvent-free ball-milling, mechanoradicals (SO4•–) were generated from persulfate via in situ homolysis in the solid state, at as low as −50 °C. These highly oxidizing radicals readily transform alkyl trifluoroborate salts to their corresponding carbon-based radicals for subsequent C–C bond formation with N-heterocycles. Mechanistic studies unambiguously confirmed the involvement

  描述了一种由机械化学促进的环保型 N-杂芳烃 C-H 烷基化新方法。在无溶剂球磨条件下，过硫酸盐在低至-50 °C 的温度下通过固态原位均解生成机械自由基 (SO 4 •– )。这些高氧化性自由基很容易将烷基三氟硼酸盐转化为相应的碳基自由基，随后与 N-杂环形成 C-C 键。机理研究明确证实了氧自由基和烷基自由基中间体的参与。
• Regioselective Sonogashira Couplings of 2,4-Dibromoquinolines. A Correction
  作者：Jason M. Nolan、Daniel L. Comins

  DOI：10.1021/jo034122w

  日期：2003.5.1

  Heteronuclear multiple bond correlation (HMBC) was used to determine the regiochemical outcome of palladium-catalyzed carbon-carbon bond formation between 2,4-dibromoquinolines and terminal acetylenes. The observed regioselectivity of these coupling reactions is opposite to that reported in the literature for analogous reactions.