(R)-2,2'-bis(2-methoxyphenyl)-1,1'-binaphthalene | 820974-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2,2'-bis(2-methoxyphenyl)-1,1'-binaphthalene
• 英文别名: 2,2'-Bis(2-methoxyphenyl)-1,1'-binaphthalene；2-(2-methoxyphenyl)-1-[2-(2-methoxyphenyl)naphthalen-1-yl]naphthalene
• CAS: 820974-51-4
• 化学式: C₃₄H₂₆O₂
• 分子量: 466.579
• InChiKey: HLDMYTMWVOSOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2,2'-bis(2-methoxyphenyl)-1,1'-binaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(R)-2,2'-(1,1'-binaphthalene-2,2'-diyl)bisphenol
  参考文献：
  名称：

  Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

  摘要：

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.041
• 作为产物：
  描述：

  2-methoxyphenyllithium 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)-2,2'-bis(2-methoxyphenyl)-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

文献信息

• The development of an approach toward sterically-hindered chiral 2′-aryl-1,1′-binaphthalenes functionalized at position 2
  作者：Michaela Mešková、Martin Putala

  DOI：10.1016/j.tetlet.2011.08.046

  日期：2011.10

  Several approaches were examined for the preparation of 1,1'-binaphthalene derivatives bearing sterically demanding ortho-substituted aryl at position 2' which are suitable for further functionalization at position 2. Steric hindrance of ortho-substituted aryl groups was critical for the approach through BINOL monotriflate. Among variations of cross-coupling reactions of 2,2'-dihalo-1,1'-binaphthalenes, Negishi arylation of an enantiopure 2,2'-dibromide was found to be the method of choice for regioselective and stereoconservative preparation of the target 2'-monoarylated precursor. Functionalization of the latter at position 2 was demonstrated by bromine substitution via lithiation followed by the reaction with several electrophiles. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis
  作者：Natalia Miklášová、Ondřej Julínek、Michaela Mešková、Vladimír Setnička、Marie Urbanová、Martin Putala

  DOI：10.1016/j.tetlet.2010.02.041

  日期：2010.4

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.