2,2'-bis(chloromethyl)-4-(dimethylamino)-4'-cyano-1,1'-biphenyl | 828916-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2'-bis(chloromethyl)-4-(dimethylamino)-4'-cyano-1,1'-biphenyl
• 英文别名: 3-(Chloromethyl)-4-[2-(chloromethyl)-4-(dimethylamino)phenyl]benzonitrile；3-(chloromethyl)-4-[2-(chloromethyl)-4-(dimethylamino)phenyl]benzonitrile
• CAS: 828916-49-0
• 化学式: C₁₇H₁₆Cl₂N₂
• 分子量: 319.233
• InChiKey: RLLQTRYPVBTPIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙硫基乙硫醇 、 2,2'-bis(chloromethyl)-4-(dimethylamino)-4'-cyano-1,1'-biphenyl 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以65%的产率得到4-(dimethylamino)-2,2'-bis-(2-ethylsulfanyl-ethyl-sulfanylmethyl)-4'-cyano-1,1'-biphenyl
  参考文献：
  名称：

  Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore

  摘要：

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.056
• 作为产物：
  描述：

  4-溴-3-甲基苯甲腈 在 溴化铵 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 氯化亚砜 、 水 、 sodium acetate 、 cesium fluoride 、 calcium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2,2'-bis(chloromethyl)-4-(dimethylamino)-4'-cyano-1,1'-biphenyl
  参考文献：
  名称：

  Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore

  摘要：

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.056

文献信息

• Fluorescence sensing based on cation-induced conformational switching: copper-selective modulation of the photoinduced intramolecular charge transfer of a donor–acceptor biphenyl fluorophore
  作者：John Cody、Christoph J. Fahrni

  DOI：10.1016/j.tet.2004.08.056

  日期：2004.11

  The fluorescence emission energy of donor-acceptor substituted biphenyls is highly sensitive towards conformational changes of the interannular twist angle. By integrating 4-dimethylamino-4'-cyano-biphenyl into the ligand backbone of a thioether-rich metal receptor we designed a fluorescence sensor that exhibits high selectivity towards copper. Upon metal binding the ligand undergoes a significant conformational change, which induces a strong hypsochromic shift of the photoinduced charge-transfer emission. Steady-state absorption and fluorescence spectroscopy revealed a high affinity towards Cu(I) with a well-defined 1:1 metal-ligand complex stoichiometry. The nature of the conformational changes upon Cu(I) coordination were analyzed in detail by H-1 NMR and 2D NOESY experiments. The spectroscopic data provide a coherent picture, which is consistent with a Boltzmann ground-state distribution of several rotamers, that are locked into a more flattened geometry upon coordination of Cu(I). (C) 2004 Elsevier Ltd. All rights reserved.