1-(2,6-diethynylphenyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2,6-diethynylphenyl)naphthalene
• 英文别名: 1-(2,6-Diethynylphenyl)naphthalene
• 化学式: C₂₀H₁₂
• 分子量: 252.315
• InChiKey: LFHJIHMEYJCCIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2,6-diethynylphenyl)naphthalene 在 copper(I) trifluoromethanesulfonate benzene 、 氢气 、 2,6-bis-[4-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-oxazol-2-yl]-pyridine 作用下， 以 水 为溶剂， 反应 15.0h， 生成 4,’4-(2-(naphthalen-1-yl)-1,3-phenylene)bis(1-benzyl-1H-1,2,3-triazole)
  参考文献：
  名称：

  Enantioposition-Selective Copper-Catalyzed Azide–Alkyne Cycloaddition for Construction of Chiral Biaryl Derivatives

  摘要：

  A highly enantioposition-selective copper-catalyzed azidealkyne cycloaddition (CuAAC) of dialkynes bearing prochiral biaryls has been developed for the construction of 1,2,3-triazoles bearing axially chiral biaryl groups in up to 76% yield and up to 99% ee.

  DOI：

  10.1021/ol502778j
• 作为产物：
  描述：

  1-(2,6-dibromophenyl)naphthalene 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 36.0h， 生成 1-(2,6-diethynylphenyl)naphthalene
  参考文献：
  名称：

  Enantioposition-Selective Copper-Catalyzed Azide–Alkyne Cycloaddition for Construction of Chiral Biaryl Derivatives

  摘要：

  A highly enantioposition-selective copper-catalyzed azidealkyne cycloaddition (CuAAC) of dialkynes bearing prochiral biaryls has been developed for the construction of 1,2,3-triazoles bearing axially chiral biaryl groups in up to 76% yield and up to 99% ee.

  DOI：

  10.1021/ol502778j

文献信息

• Mechanistic Insights into Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC): Observation of Asymmetric Amplification
  作者：Yasuhiro Uozumi、Takao Osako

  DOI：10.1055/s-0034-1380534

  日期：——

  A mechanistic study of copper-catalyzed azide-alkyne cycloaddition (CuAAC) was examined using an enantioposition-selective asymmetric CuAAC as a probe reaction system. Based on the observed asymmetric amplification (a positive nonlinear effect), we proposed that a dimeric chiral copper complex is involved as a reactive intermediate in the copper-catalyzed azide-alkyne cycloaddition.
• Enantioposition-Selective Copper-Catalyzed Azide–Alkyne Cycloaddition for Construction of Chiral Biaryl Derivatives
  作者：Takao Osako、Yasuhiro Uozumi

  DOI：10.1021/ol502778j

  日期：2014.11.21

  A highly enantioposition-selective copper-catalyzed azidealkyne cycloaddition (CuAAC) of dialkynes bearing prochiral biaryls has been developed for the construction of 1,2,3-triazoles bearing axially chiral biaryl groups in up to 76% yield and up to 99% ee.