1-bromo-2-methoxy-6-(2'(4''-pyridyl)ethenyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-bromo-2-methoxy-6-(2'(4''-pyridyl)ethenyl)naphthalene
• 英文别名: 4-[(E)-2-(5-bromo-6-methoxynaphthalen-2-yl)ethenyl]pyridine
• 化学式: C₁₈H₁₄BrNO
• 分子量: 340.219
• InChiKey: TUXMJBTUJTZBMD-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-乙酰氧基苯乙烯 、 1-bromo-2-methoxy-6-(2'(4''-pyridyl)ethenyl)naphthalene 在 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 三乙胺 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 以19%的产率得到[4-[(E)-2-[2-methoxy-6-[(E)-2-pyridin-4-ylethenyl]naphthalen-1-yl]ethenyl]phenyl] acetate
  参考文献：
  名称：

  Highly Conjugated Molecules from Dibromonaphthyl Derivatives and 4-Vinylpyridine or 4-Acetoxystyrene by the Heck Reaction

  摘要：

  Palladium-catalyzed coupling of 1,6- and 2,6-dibromonaphthyl derivatives with 4-vinylpyridine or 4-acetoxystyrene resulted in mono- and bis-arylvinylation depending on the choice of reaction conditions. For the 1,6-dibromoarenes, the mono-arylvinylated derivative at position-6 was the sole product in the presence of (o-tol)(3)P/Et3N. The bis-arylvinylated derivative was the major product, accompanied by a minor product, arylvinylated at position-6 and reduced at position-1, in the presence of (o-tol)(3)P/Et3N/MeCN. For the 2,6-dibromoarenes, the bis-arylvinylated derivative was the sole product in the presence of either Ph3P or (o-tol)(3)P, if provided with a small volume of Et3N/MeCN solvent, and the mono-arylvinylated derivative was the major product with larger solvent volume and higher haloarene ratio. Fluorescence intensities of 2,6-bis-arylvinylated products were 2 to 3 orders of magnitude higher than that of stilbene. Nematic phases, at relatively high temperatures, were observed for some of the rodlike molecules. Shown by H-1 NMR study, at the photostationary state of isomerization, smaller fractions of cis-form were obtained for molecules that exhibited larger fluorescence quantum yields. The results presented here are beneficial to the pursuit of nonlinear optical materials, fluorescent mesogens, photo- and electroactive materials.

  DOI：

  10.1021/jo990697a
• 作为产物：
  描述：

  4-乙烯基吡啶 、 1,6-二溴-2-甲氧基萘 在 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 三乙胺 为溶剂， 反应 96.0h， 以63%的产率得到1-bromo-2-methoxy-6-(2'(4''-pyridyl)ethenyl)naphthalene
  参考文献：
  名称：

  Highly Conjugated Molecules from Dibromonaphthyl Derivatives and 4-Vinylpyridine or 4-Acetoxystyrene by the Heck Reaction

  摘要：

  Palladium-catalyzed coupling of 1,6- and 2,6-dibromonaphthyl derivatives with 4-vinylpyridine or 4-acetoxystyrene resulted in mono- and bis-arylvinylation depending on the choice of reaction conditions. For the 1,6-dibromoarenes, the mono-arylvinylated derivative at position-6 was the sole product in the presence of (o-tol)(3)P/Et3N. The bis-arylvinylated derivative was the major product, accompanied by a minor product, arylvinylated at position-6 and reduced at position-1, in the presence of (o-tol)(3)P/Et3N/MeCN. For the 2,6-dibromoarenes, the bis-arylvinylated derivative was the sole product in the presence of either Ph3P or (o-tol)(3)P, if provided with a small volume of Et3N/MeCN solvent, and the mono-arylvinylated derivative was the major product with larger solvent volume and higher haloarene ratio. Fluorescence intensities of 2,6-bis-arylvinylated products were 2 to 3 orders of magnitude higher than that of stilbene. Nematic phases, at relatively high temperatures, were observed for some of the rodlike molecules. Shown by H-1 NMR study, at the photostationary state of isomerization, smaller fractions of cis-form were obtained for molecules that exhibited larger fluorescence quantum yields. The results presented here are beneficial to the pursuit of nonlinear optical materials, fluorescent mesogens, photo- and electroactive materials.

  DOI：

  10.1021/jo990697a

文献信息

• Highly Conjugated Molecules from Dibromonaphthyl Derivatives and 4-Vinylpyridine or 4-Acetoxystyrene by the Heck Reaction
  作者：C. C. Chang、K. J. Chen、L. J. Yu

  DOI：10.1021/jo990697a

  日期：1999.7.1

  Palladium-catalyzed coupling of 1,6- and 2,6-dibromonaphthyl derivatives with 4-vinylpyridine or 4-acetoxystyrene resulted in mono- and bis-arylvinylation depending on the choice of reaction conditions. For the 1,6-dibromoarenes, the mono-arylvinylated derivative at position-6 was the sole product in the presence of (o-tol)(3)P/Et3N. The bis-arylvinylated derivative was the major product, accompanied by a minor product, arylvinylated at position-6 and reduced at position-1, in the presence of (o-tol)(3)P/Et3N/MeCN. For the 2,6-dibromoarenes, the bis-arylvinylated derivative was the sole product in the presence of either Ph3P or (o-tol)(3)P, if provided with a small volume of Et3N/MeCN solvent, and the mono-arylvinylated derivative was the major product with larger solvent volume and higher haloarene ratio. Fluorescence intensities of 2,6-bis-arylvinylated products were 2 to 3 orders of magnitude higher than that of stilbene. Nematic phases, at relatively high temperatures, were observed for some of the rodlike molecules. Shown by H-1 NMR study, at the photostationary state of isomerization, smaller fractions of cis-form were obtained for molecules that exhibited larger fluorescence quantum yields. The results presented here are beneficial to the pursuit of nonlinear optical materials, fluorescent mesogens, photo- and electroactive materials.