2-(3-bromophenyl)-1-methyl-phenanthro[9,10-d]imidazole | 370095-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(3-bromophenyl)-1-methyl-phenanthro[9,10-d]imidazole
• 英文别名: 2-(3-Bromophenyl)-3-methylphenanthro[9,10-d]imidazole
• CAS: 370095-40-2
• 化学式: C₂₂H₁₅BrN₂
• 分子量: 387.278
• InChiKey: LIDVJTUHMKZDMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-bromophenyl)-1-methyl-phenanthro[9,10-d]imidazole 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 反应 2.5h， 生成 2,6-bis-(3-(1-methyl-phenanthro[9,10-d]imidazol-2-yl)phenyl)pyridine
  参考文献：
  名称：

  A New Versatile Receptor Platform

  摘要：

  We prepared a molecular receptor based on the molecular tweezer concept. Our system offers versatility, an extremely short synthetic route, good yield, large quantities, and finally having binding constants that equal the best known tweezer molecules when it comes to binding various nitroaromatics such as 1,3,5-trinitrotoluene (24 M-1), 1,3,5-trinitrobenzene (182 M-1), and 2,4,7-trinitrofluorenone (490 M-1) as determined using H-1 NMR in CDCl3. It is notable that these binding constants are achieved although the molecular framework is not locked in a fixed and rigid conformation. The rigidity has been claimed to be the governing factor when it comes to achieving a large binding constant. We propose that our molecular tweezer system may be preorganized and that this explains the high binding constants observed. Further, we investigated the crystal structures of both the neutral receptor molecule and a complex with 1,3,5-trinitrobenzene and found that the molecule forms a pocket suited to accommodate flat aromatic analytes.

  DOI：

  10.1021/jo015690j
• 作为产物：
  描述：

  2-(3-bromophenyl)-1H-phenanthro[9,10-d]imidazole acetate 、 碘甲烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以74%的产率得到2-(3-bromophenyl)-1-methyl-phenanthro[9,10-d]imidazole
  参考文献：
  名称：

  A New Versatile Receptor Platform

  摘要：

  We prepared a molecular receptor based on the molecular tweezer concept. Our system offers versatility, an extremely short synthetic route, good yield, large quantities, and finally having binding constants that equal the best known tweezer molecules when it comes to binding various nitroaromatics such as 1,3,5-trinitrotoluene (24 M-1), 1,3,5-trinitrobenzene (182 M-1), and 2,4,7-trinitrofluorenone (490 M-1) as determined using H-1 NMR in CDCl3. It is notable that these binding constants are achieved although the molecular framework is not locked in a fixed and rigid conformation. The rigidity has been claimed to be the governing factor when it comes to achieving a large binding constant. We propose that our molecular tweezer system may be preorganized and that this explains the high binding constants observed. Further, we investigated the crystal structures of both the neutral receptor molecule and a complex with 1,3,5-trinitrobenzene and found that the molecule forms a pocket suited to accommodate flat aromatic analytes.

  DOI：

  10.1021/jo015690j