1-ethynyl-5-nitronaphthalene | 476181-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-ethynyl-5-nitronaphthalene
• 英文别名: 1-ethynyl-5-nitro-naphthalene；1-Aethinyl-5-nitro-naphthalin
• CAS: 476181-85-8
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: ZUGKVOHRBROLRF-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C(Solv: ethanol (64-17-5))
• 沸点：
  350.5±17.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethynyl-5-nitronaphthalene 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 作用下， 以 三乙胺 、 甲苯 为溶剂， 反应 27.0h， 生成 1-ethynyl-5-[(5-nitro-1-naphthyl)ethynyl]naphthalene
  参考文献：
  名称：

  Carbon Networks Based on 1,5-Naphthalene Units. Synthesis of 1,5-Naphthalene Nanostructures with Extended π-Conjugation

  摘要：

  The synthesis and spectroscopic characterization of nanometer-sized conjugated molecules of 5-X-naphthylethynyl (X = NO2, NMe2) units with precise length and constitution have been carried out. A new extended pi-conjugated 5-nitronaphthyl family was synthesized by palladium-catalyzed cross-coupling reaction between the protected 5-iodonaphthylethynyl 5a and 1-ethynyl-5-nitronaphthalene 9, or the resulting ethynyl compound 11 and the 1-iodo-5-nitronaphthalene 3. Catalytic oxidative dimerization of the terminal acetylene compounds permits the isolation of the corresponding 1,3-butadiyne derivatives 16-18, with the nitro groups at the ends of the conjugation, in excellent yields. A new family of conjugated 5-nitro-(naphthylethynyl)-[5-(N,N-dimethylamino)]naphthalene (20-22), was also synthesized by palladium-catalyzed cross-coupling reaction between 5-iodo-N,N-dimethylnaphthalene-1-amine (19) with the appropriate terminal acetylene (9, 11, and 13 respectively). Compounds 20-22 show a fluorescence emission and also exhibit a charge-transfer absorption in the visible spectrum. X-ray structure of 20 confirms a centrosymmetric dimer association with an interplanar distance of 3.43 Angstrom, and the naphthalene rings adopt an anti conformation around the Cequivalent toC triple bond.

  DOI：

  10.1021/jo0203589
• 作为产物：
  描述：

  1,5-二硝基萘 在 sodium sulfide 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 氯化铵 、 尿素 、 potassium iodide 、 sodium nitrite 作用下， 以 硫酸 、 水 、 溶剂黄146 、 三乙胺 、 甲苯 为溶剂， 反应 37.0h， 生成 1-ethynyl-5-nitronaphthalene
  参考文献：
  名称：

  Carbon Networks Based on 1,5-Naphthalene Units. Synthesis of 1,5-Naphthalene Nanostructures with Extended π-Conjugation

  摘要：

  The synthesis and spectroscopic characterization of nanometer-sized conjugated molecules of 5-X-naphthylethynyl (X = NO2, NMe2) units with precise length and constitution have been carried out. A new extended pi-conjugated 5-nitronaphthyl family was synthesized by palladium-catalyzed cross-coupling reaction between the protected 5-iodonaphthylethynyl 5a and 1-ethynyl-5-nitronaphthalene 9, or the resulting ethynyl compound 11 and the 1-iodo-5-nitronaphthalene 3. Catalytic oxidative dimerization of the terminal acetylene compounds permits the isolation of the corresponding 1,3-butadiyne derivatives 16-18, with the nitro groups at the ends of the conjugation, in excellent yields. A new family of conjugated 5-nitro-(naphthylethynyl)-[5-(N,N-dimethylamino)]naphthalene (20-22), was also synthesized by palladium-catalyzed cross-coupling reaction between 5-iodo-N,N-dimethylnaphthalene-1-amine (19) with the appropriate terminal acetylene (9, 11, and 13 respectively). Compounds 20-22 show a fluorescence emission and also exhibit a charge-transfer absorption in the visible spectrum. X-ray structure of 20 confirms a centrosymmetric dimer association with an interplanar distance of 3.43 Angstrom, and the naphthalene rings adopt an anti conformation around the Cequivalent toC triple bond.

  DOI：

  10.1021/jo0203589

文献信息

• Sergiewskaja; Lewschina, Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1480,1485; engl. Ausg. S. 1543, 1546
  作者：Sergiewskaja、Lewschina

  DOI：——

  日期：——
• US4215226A
  申请人：——

  公开号：US4215226A

  公开（公告）日：1980-07-29