2-(3-Ethynyl-phenylethynyl)-2'-phenylethynyl-[1,1']binaphthalenyl | 763109-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-Ethynyl-phenylethynyl)-2'-phenylethynyl-[1,1']binaphthalenyl
• CAS: 763109-17-7
• 化学式: C₃₈H₂₂
• 分子量: 478.593
• InChiKey: HZJOWRGPITWGCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  38.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2-Bromo-6-[2-[6-[2-(4-hexylphenyl)ethynyl]pyridin-2-yl]ethynyl]pyridine 、 2-(3-Ethynyl-phenylethynyl)-2'-phenylethynyl-[1,1']binaphthalenyl 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以61%的产率得到2-[2-(4-Hexylphenyl)ethynyl]-6-[2-[6-[2-[3-[2-[1-[2-(2-phenylethynyl)naphthalen-1-yl]naphthalen-2-yl]ethynyl]phenyl]ethynyl]pyridin-2-yl]ethynyl]pyridine
  参考文献：
  名称：

  Metal-Assisted Assembly of Pyridine-Containing Arylene Ethynylene Strands to Enantiopure Double Helicates

  摘要：

  Pyridine-containing arylene ethynylene strands were connected to the 2- and 2'-positions of (R)- and (S)-1,1'-binaphthyl templates. The arylene ethynylene moieties underwent intramolecular coordination with Ag(I) or Cu(I) ion to afford enantiopure double helicates. The double-helical structure was elucidated on the basis of circular dichroic (CD) spectra. The importance of intramolecular complexation of the double strands for the helicate formation was confirmed by comparison with a ligand bearing a single strand. Connection of the strands through an ether linkage enabled a sorting out of the Cotton effect induced by double-helical arylene ethynylene moieties. The CD exciton chirality method unambiguously proved that the termini of the strands approach each other upon complexation and that the sense of the induced helicity is the same as predicted by molecular modeling.

  DOI：

  10.1021/ja048327d
• 作为产物：
  描述：

  Trimethyl-[3-(2'-phenylethynyl-[1,1']binaphthalenyl-2-ylethynyl)-phenylethynyl]-silane 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以98%的产率得到2-(3-Ethynyl-phenylethynyl)-2'-phenylethynyl-[1,1']binaphthalenyl
  参考文献：
  名称：

  Metal-Assisted Assembly of Pyridine-Containing Arylene Ethynylene Strands to Enantiopure Double Helicates

  摘要：

  Pyridine-containing arylene ethynylene strands were connected to the 2- and 2'-positions of (R)- and (S)-1,1'-binaphthyl templates. The arylene ethynylene moieties underwent intramolecular coordination with Ag(I) or Cu(I) ion to afford enantiopure double helicates. The double-helical structure was elucidated on the basis of circular dichroic (CD) spectra. The importance of intramolecular complexation of the double strands for the helicate formation was confirmed by comparison with a ligand bearing a single strand. Connection of the strands through an ether linkage enabled a sorting out of the Cotton effect induced by double-helical arylene ethynylene moieties. The CD exciton chirality method unambiguously proved that the termini of the strands approach each other upon complexation and that the sense of the induced helicity is the same as predicted by molecular modeling.

  DOI：

  10.1021/ja048327d