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

中文名称
——
中文别名
——
英文名称
1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene
英文别名
3-(8-Naphthalen-1-ylnaphthalen-1-yl)pyridine
1-(1'-naphthyl)-8-(3'-pyridyl)naphthalene化学式
CAS
——
化学式
C25H17N
mdl
——
分子量
331.417
InChiKey
KTQVKPFYIKXTAO-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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四(三苯基膦)钯 、 sodium carbonate 作用下, 以 乙二醇二甲醚 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
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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.
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