2,9-Bis(2',6'-dihydroxyphenyl)-1,10-phenanthroline hydrochloride | 124318-74-7

• 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'-dihydroxyphenyl)-1,10-phenanthroline hydrochloride
• CAS: 124318-74-7
• 化学式: C₂₄H₁₆N₂O₄*ClH
• 分子量: 432.863
• InChiKey: XXWPTHFJMAHPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106.7
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,9-Bis(2',6'-dihydroxyphenyl)-1,10-phenanthroline hydrochloride 在 Grubbs catalyst first generation CsCO₃ 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,9)-1,10-phenanthrolinabicyclo[12.12.1]heptacosaphan-7,20-diene
  参考文献：
  名称：

  Concave 1,10-Phenanthrolines by Ring-Closing Metathesis

  摘要：

  Ring-closing metathesis using Grubbs' catalyst has been applied to the synthesis of the concave 1,10-phenanthrolines 5. Instead of a kinetically controlled double macrocyclization of the tetraphenol precursor 2 by two equivalents of ditosylates or diiodides, the new three step synthesis separates the alkylation of 2 from the macrocyclization. After the tetraalkylation of 2, the resulting tetraalkene 3 is cyclized by metathesis under thermodynamic control to give the bimacrocycles 4 in up to 92% yield. Hydrogenation of the alkene double bonds gave the bimacrocycles 5 in considerably improved overall yields (for instance for 5b from 19 to 79%).

  DOI：

  10.1002/1099-0690(200106)2001:11<2161::aid-ejoc2161>3.0.co;2-2
• 作为产物：
  描述：

  1,10-亚铁试剂(邻二氮杂菲),2,9-二(2,6-二甲氧苯基)- 在 吡啶盐酸盐 作用下， 反应 3.0h， 以83%的产率得到2,9-Bis(2',6'-dihydroxyphenyl)-1,10-phenanthroline hydrochloride
  参考文献：
  名称：

  Concave 1,10-Phenanthrolines by Ring-Closing Metathesis

  摘要：

  Ring-closing metathesis using Grubbs' catalyst has been applied to the synthesis of the concave 1,10-phenanthrolines 5. Instead of a kinetically controlled double macrocyclization of the tetraphenol precursor 2 by two equivalents of ditosylates or diiodides, the new three step synthesis separates the alkylation of 2 from the macrocyclization. After the tetraalkylation of 2, the resulting tetraalkene 3 is cyclized by metathesis under thermodynamic control to give the bimacrocycles 4 in up to 92% yield. Hydrogenation of the alkene double bonds gave the bimacrocycles 5 in considerably improved overall yields (for instance for 5b from 19 to 79%).

  DOI：

  10.1002/1099-0690(200106)2001:11<2161::aid-ejoc2161>3.0.co;2-2