1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene
• 英文别名: 3-(8-Naphthalen-1-ylnaphthalen-1-yl)pyridine
• 化学式: C₂₅H₁₇N
• 分子量: 331.417
• InChiKey: KTQVKPFYIKXTAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene 、 碘甲烷 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到3-[1,1']Binaphthalenyl-8-yl-1-methyl-pyridinium; iodide
  参考文献：
  名称：

  π-Cation and π-Dipole-Stabilizing Interactions in a Simple Model System with Cofacial Aromatic Rings

  摘要：

  Four 1,8-disubstituted naphthalenes having a l-naphthyl ring cofacial to a second ring were prepared by a Suzuki-type coupling of a bromide with a borane, a boronic acid, or a boronic ester in the presence of Pd(0). The second ring is either a positively charged N-methylated 3-pyridyl (4A) or a 3-(trimethylammonio)phenyl group (7A) or a neutral 3-tolyl (5) or 3-(dimethylamino)phenyl (7) ring. At ambient temperatures, all exhibit atropisomerism. The syn isomer predominates over the anti form, suggesting that pi-charge and pi-dipole electrostatic through-space interactions preferentially stabilize the more sterically hindered syn isomer. The largest preference for the syn isomer, a factor of 3.1, was found for the trimethylammonio substrate-7A in CDCl3. Semiempirical computations (AM1 and PM3) predict that the syn isomer is lower in energy than the anti form of the positively charged compounds, but the preference for the neutral compounds is small enough to be ambiguous.

  DOI：

  10.1021/jo9801465
• 作为产物：
  描述：

  二乙基(3-吡啶基)-硼烷 、 8-bromo-1,1'-binaphthalene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 以72%的产率得到1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene
  参考文献：
  名称：

  π-Cation and π-Dipole-Stabilizing Interactions in a Simple Model System with Cofacial Aromatic Rings

  摘要：

  Four 1,8-disubstituted naphthalenes having a l-naphthyl ring cofacial to a second ring were prepared by a Suzuki-type coupling of a bromide with a borane, a boronic acid, or a boronic ester in the presence of Pd(0). The second ring is either a positively charged N-methylated 3-pyridyl (4A) or a 3-(trimethylammonio)phenyl group (7A) or a neutral 3-tolyl (5) or 3-(dimethylamino)phenyl (7) ring. At ambient temperatures, all exhibit atropisomerism. The syn isomer predominates over the anti form, suggesting that pi-charge and pi-dipole electrostatic through-space interactions preferentially stabilize the more sterically hindered syn isomer. The largest preference for the syn isomer, a factor of 3.1, was found for the trimethylammonio substrate-7A in CDCl3. Semiempirical computations (AM1 and PM3) predict that the syn isomer is lower in energy than the anti form of the positively charged compounds, but the preference for the neutral compounds is small enough to be ambiguous.

  DOI：

  10.1021/jo9801465

文献信息

• π-Cation and π-Dipole-Stabilizing Interactions in a Simple Model System with Cofacial Aromatic Rings
  作者：John A. Zoltewicz、Norbert M. Maier、Walter M. F. Fabian

  DOI：10.1021/jo9801465

  日期：1998.7.1

  Four 1,8-disubstituted naphthalenes having a l-naphthyl ring cofacial to a second ring were prepared by a Suzuki-type coupling of a bromide with a borane, a boronic acid, or a boronic ester in the presence of Pd(0). The second ring is either a positively charged N-methylated 3-pyridyl (4A) or a 3-(trimethylammonio)phenyl group (7A) or a neutral 3-tolyl (5) or 3-(dimethylamino)phenyl (7) ring. At ambient temperatures, all exhibit atropisomerism. The syn isomer predominates over the anti form, suggesting that pi-charge and pi-dipole electrostatic through-space interactions preferentially stabilize the more sterically hindered syn isomer. The largest preference for the syn isomer, a factor of 3.1, was found for the trimethylammonio substrate-7A in CDCl3. Semiempirical computations (AM1 and PM3) predict that the syn isomer is lower in energy than the anti form of the positively charged compounds, but the preference for the neutral compounds is small enough to be ambiguous.