2-(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline | 320573-12-4

• 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: 2-(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline
• 英文别名: 2-[8-Bromo-2-(2,6-dimethoxyphenyl)-1,10-phenanthrolin-3-yl]ethynyl-trimethylsilane；2-[8-bromo-2-(2,6-dimethoxyphenyl)-1,10-phenanthrolin-3-yl]ethynyl-trimethylsilane
• CAS: 320573-12-4
• 化学式: C₂₅H₂₃BrN₂O₂Si
• 分子量: 491.459
• InChiKey: SMCBONKPYXKKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline 在 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 11.0h， 生成 2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-8-bromo-1,10-phenanthroline
  参考文献：
  名称：

  A Highly Regioselective Sonogashira Coupling as a Key Step in the Preparation of the First Phenanthroline with Two Diverse Reactive Groups in 3,8-Positions

  摘要：

  The preparation of 3,8-unsymmetric phenanthrolines is described. Desymmetrization of 3,8-dibromophenanthroline was achieved after monoarylation followed by regioselective Pd-catalyzed monoalkynylation that was controlled by the methoxy group of the dimethoxyphenyl substituent.

  DOI：

  10.1021/ol006514k
• 作为产物：
  描述：

  3,8-二溴菲罗啉 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 苯 为溶剂， 反应 54.5h， 生成 2-(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline
  参考文献：
  名称：

  A Highly Regioselective Sonogashira Coupling as a Key Step in the Preparation of the First Phenanthroline with Two Diverse Reactive Groups in 3,8-Positions

  摘要：

  The preparation of 3,8-unsymmetric phenanthrolines is described. Desymmetrization of 3,8-dibromophenanthroline was achieved after monoarylation followed by regioselective Pd-catalyzed monoalkynylation that was controlled by the methoxy group of the dimethoxyphenyl substituent.

  DOI：

  10.1021/ol006514k

文献信息

• A Highly Regioselective Sonogashira Coupling as a Key Step in the Preparation of the First Phenanthroline with Two Diverse Reactive Groups in 3,8-Positions
  作者：Shi-Xia Liu、Christoph Michel、Michael Schmittel

  DOI：10.1021/ol006514k

  日期：2000.12.1

  The preparation of 3,8-unsymmetric phenanthrolines is described. Desymmetrization of 3,8-dibromophenanthroline was achieved after monoarylation followed by regioselective Pd-catalyzed monoalkynylation that was controlled by the methoxy group of the dimethoxyphenyl substituent.