| 672325-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 672325-68-7
• 化学式: C₉H₁₁BrZn
• 分子量: 264.48
• InChiKey: YVWXRRVRPNXOOL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  、 (R)-2,2'-二碘-1,1'-联萘 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以75%的产率得到(R)-2,2'-bis(2-isopropylphenyl)-1,1'-binaphthalene
  参考文献：
  名称：

  Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2,2′-diaryl-1,1′-binaphthalenes

  摘要：

  A series of ortho-substituted 2,2 '-aryl-1,1 '-binaphthalenes were prepared via Negishi arylation of 2,2 '-diiodo-1,1 '-binaphthalene in good to high yields (65-95%) as an equilibrium mixtures of up to three atropisomers (unlike,unlike, like,unlike, and like,like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP functional comprising solvent permittivity were, apart from the toluene solution, which was expected to interact with the aromatic solute, in qualitative agreement with the experimental values. In the case of the ditolyl derivative, the population of the atropisomers was confirmed by CD spectroscopy via comparison with the population-weighted averaged spectrum computed using the M06 functional. X-ray structure analyses of particular atropisomers of the dianisyl, dianilinyl, and dinaphthyl derivatives are also presented and discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.005
• 作为产物：
  描述：

  2-碘异丙基苯 在 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2,2′-diaryl-1,1′-binaphthalenes

  摘要：

  A series of ortho-substituted 2,2 '-aryl-1,1 '-binaphthalenes were prepared via Negishi arylation of 2,2 '-diiodo-1,1 '-binaphthalene in good to high yields (65-95%) as an equilibrium mixtures of up to three atropisomers (unlike,unlike, like,unlike, and like,like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP functional comprising solvent permittivity were, apart from the toluene solution, which was expected to interact with the aromatic solute, in qualitative agreement with the experimental values. In the case of the ditolyl derivative, the population of the atropisomers was confirmed by CD spectroscopy via comparison with the population-weighted averaged spectrum computed using the M06 functional. X-ray structure analyses of particular atropisomers of the dianisyl, dianilinyl, and dinaphthyl derivatives are also presented and discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.005

文献信息

• Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2,2′-diaryl-1,1′-binaphthalenes
  作者：Marcel Ehn、Nikolay Georgiev Vassilev、Peter Kasák、Branislav Horváth、Juraj Filo、Kurt Mereiter、Erik Rakovský、Martin Putala

  DOI：10.1016/j.tetasy.2013.09.005

  日期：2013.10

  A series of ortho-substituted 2,2 '-aryl-1,1 '-binaphthalenes were prepared via Negishi arylation of 2,2 '-diiodo-1,1 '-binaphthalene in good to high yields (65-95%) as an equilibrium mixtures of up to three atropisomers (unlike,unlike, like,unlike, and like,like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP functional comprising solvent permittivity were, apart from the toluene solution, which was expected to interact with the aromatic solute, in qualitative agreement with the experimental values. In the case of the ditolyl derivative, the population of the atropisomers was confirmed by CD spectroscopy via comparison with the population-weighted averaged spectrum computed using the M06 functional. X-ray structure analyses of particular atropisomers of the dianisyl, dianilinyl, and dinaphthyl derivatives are also presented and discussed. (C) 2013 Elsevier Ltd. All rights reserved.