2-methyl-4-{5-[(5-nitro-1-naphthyl)ethynyl]-1-naphthyl}but-3-yn-2-ol | 476181-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-4-{5-[(5-nitro-1-naphthyl)ethynyl]-1-naphthyl}but-3-yn-2-ol
• 英文别名: 2-Methyl-4-[5-[2-(5-nitronaphthalen-1-yl)ethynyl]naphthalen-1-yl]but-3-yn-2-ol
• CAS: 476181-86-9
• 化学式: C₂₇H₁₉NO₃
• 分子量: 405.453
• InChiKey: CYRBLLIXDSIYEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-{5-[(5-nitro-1-naphthyl)ethynyl]-1-naphthyl}but-3-yn-2-ol 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 36.0h， 生成 1-nitro-5-({5-[(5-nitro-1-naphthyl)ethynyl]-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-碘-5-硝基萘 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 48.0h， 生成 2-methyl-4-{5-[(5-nitro-1-naphthyl)ethynyl]-1-naphthyl}but-3-yn-2-ol
  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