2,9-bis(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline | 320573-13-5

• 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: 2,9-bis(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline
• 英文别名: 2-[8-Bromo-2,9-bis(2,6-dimethoxyphenyl)-1,10-phenanthrolin-3-yl]ethynyl-trimethylsilane；2-[8-bromo-2,9-bis(2,6-dimethoxyphenyl)-1,10-phenanthrolin-3-yl]ethynyl-trimethylsilane
• CAS: 320573-13-5
• 化学式: C₃₃H₃₁BrN₂O₄Si
• 分子量: 627.61
• InChiKey: HMLIQEACWPPPHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,9-bis(2,6-dimethoxyphenyl)-3-trimethylsilylethynyl-8-bromo-1,10-phenanthroline 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以80%的产率得到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 62.5h， 生成 2,9-bis(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.