(R,S,S)-1,2':1',1'':2'',1'''-Quaternaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R,S,S)-1,2':1',1'':2'',1'''-Quaternaphthalene
• 英文别名: 2-Naphthalen-1-yl-1-(2-naphthalen-1-ylnaphthalen-1-yl)naphthalene；2-naphthalen-1-yl-1-(2-naphthalen-1-ylnaphthalen-1-yl)naphthalene
• 化学式: C₄₀H₂₆
• 分子量: 506.646
• InChiKey: BKJSKIITVAAPDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  8.0
• 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

• 作为产物：
  描述：

  naphthalen-1-yl-lithium 在 四(三苯基膦)钯 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 (R,S,S)-1,2':1',1'':2'',1'''-Quaternaphthalene
  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

• Suzuki Coupling of Chiral 1,1′-Binaphthyl Systems − New Synthetic Routes to Functionalize the 2- and 2,2′-Positions
  作者：Birgit Schilling、Dieter E. Kaufmann

  DOI：10.1002/(sici)1099-0690(199804)1998:4<701::aid-ejoc701>3.0.co;2-e

  日期：1998.4

  2′-arylated 1,1′-binaphthyls can be synthesized. Selective monoarylation of 3, 4 and 5 can be performed. Subsequent and stepwise arylation offers general access to unsymmetrically substituted binaphthyls. Moreover, interesting atropisomeric complex molecules, such as 4,4′-bis[2-(1,1′-binaphthyl)]-1,1′-biphenyl (18a), are accessible. Compounds of type 18, which can be obtained by twofold Pd-catalyzed coupling

  在钯催化的 Suzuki 偶联反应中使用在 2-或 2,2'-位取代的 1,1'-联萘衍生物 1-5。单和双硼化偶联组分 2、4 和 5 可以很容易地制备和纯化，在空气中稳定，因此是 Suzuki 与几种芳基卤化物偶联反应的有趣起始材料。因此，可以合成多种新的轴向手性 2- 和 2,2'-芳基化 1,1'-联萘。可以进行 3、4 和 5 的选择性单芳基化。随后的逐步芳基化提供了对不对称取代的联萘的通用访问。此外，还可以使用有趣的阻转异构复合分子，例如 4,4'-双 [2-(1,1'-联萘)]-1,1'-联苯 (18a)。18 型化合物，可通过双重 Pd 催化偶联反应获得，
• 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.