4,4''-dibromo-2,5,2'',5''-tetra-n-hexyloxy-p-terphenyl | 251650-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4''-dibromo-2,5,2'',5''-tetra-n-hexyloxy-p-terphenyl
• 英文别名: 1-Bromo-4-[4-(4-bromo-2,5-dihexoxyphenyl)phenyl]-2,5-dihexoxybenzene
• CAS: 251650-25-6
• 化学式: C₄₂H₆₀Br₂O₄
• 分子量: 788.744
• InChiKey: VWTCOEMYZPURSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  48
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4''-dibromo-2,5,2'',5''-tetra-n-hexyloxy-p-terphenyl 在 正丁基锂 、 硼酸三乙酯 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以88%的产率得到[4-[4-(4-Borono-2,5-dihexoxyphenyl)phenyl]-2,5-dihexoxyphenyl]boronic acid
  参考文献：
  名称：

  From Highly Enantioselective Monomeric Catalysts to Highly Enantioselective Polymeric Catalysts:  Application of Rigid and Sterically Regular Chiral Binaphthyl Polymers to the Asymmetric Synthesis of Chiral Secondary Alcohols

  摘要：

  A 1,1'-binaphthyl-based polymeric chiral catalyst with the most general enantioselectivity for the alkylzinc addition to a broad range of aldehydes has been obtained. This polymer can be easily recovered, and the recycled polymer shows the same catalytic properties as the original polymer. A highly enantioselective catalytic diphenylzinc addition to aldehydes has also been achieved by using the chiral binaphthyl monomer and polymer catalysts. Particularly, the excellent enantioselectivity observed for the addition of diphenylzinc to aromatic aldehydes allows the preparation of optically active diaryl carbinols that are synthetically useful but difficult to access by asymmetric catalysis. A novel asymmetric reduction of ketones catalyzed by the mono- and polybinaphthyl zinc complexes has been discovered. Our work on the asymmetric organozinc addition to aldehydes and the asymmetric reduction of ketones catalyzed by the zinc complexes of chiral binaphthyl monomer (R)-12 and polybinaphthyl (R)-43 has not only provided new methods to prepare optically active secondary alcohols but also demonstrated that incorporation of an enantioselective monomeric catalyst into a rigid and sterically regular polymer structure could almost completely preserve the catalytic properties of the monomeric catalyst. This strategy may find general application in converting existing highly enantioselective monomer catalysts into polymer catalysts of similar enantioselectivity provided that the catalytically active species of the monomer catalysts contain only the monomeric units rather than the aggregates of the monomers. By using this strategy, it is possible to overcame the drawbacks associated with the traditional approach to preparing polymeric chiral catalysts where the microenvironments of the catalytic sites in the polymers are often significantly altered from those in the monomeric catalysts due to the flexible and sterically irregular polymer chains.

  DOI：

  10.1021/jo990992v
• 作为产物：
  描述：

  1,4-二溴-2,5-二(己氧基)苯 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 生成 4,4''-dibromo-2,5,2'',5''-tetra-n-hexyloxy-p-terphenyl
  参考文献：
  名称：

  From Highly Enantioselective Monomeric Catalysts to Highly Enantioselective Polymeric Catalysts:  Application of Rigid and Sterically Regular Chiral Binaphthyl Polymers to the Asymmetric Synthesis of Chiral Secondary Alcohols

  摘要：

  A 1,1'-binaphthyl-based polymeric chiral catalyst with the most general enantioselectivity for the alkylzinc addition to a broad range of aldehydes has been obtained. This polymer can be easily recovered, and the recycled polymer shows the same catalytic properties as the original polymer. A highly enantioselective catalytic diphenylzinc addition to aldehydes has also been achieved by using the chiral binaphthyl monomer and polymer catalysts. Particularly, the excellent enantioselectivity observed for the addition of diphenylzinc to aromatic aldehydes allows the preparation of optically active diaryl carbinols that are synthetically useful but difficult to access by asymmetric catalysis. A novel asymmetric reduction of ketones catalyzed by the mono- and polybinaphthyl zinc complexes has been discovered. Our work on the asymmetric organozinc addition to aldehydes and the asymmetric reduction of ketones catalyzed by the zinc complexes of chiral binaphthyl monomer (R)-12 and polybinaphthyl (R)-43 has not only provided new methods to prepare optically active secondary alcohols but also demonstrated that incorporation of an enantioselective monomeric catalyst into a rigid and sterically regular polymer structure could almost completely preserve the catalytic properties of the monomeric catalyst. This strategy may find general application in converting existing highly enantioselective monomer catalysts into polymer catalysts of similar enantioselectivity provided that the catalytically active species of the monomer catalysts contain only the monomeric units rather than the aggregates of the monomers. By using this strategy, it is possible to overcame the drawbacks associated with the traditional approach to preparing polymeric chiral catalysts where the microenvironments of the catalytic sites in the polymers are often significantly altered from those in the monomeric catalysts due to the flexible and sterically irregular polymer chains.

  DOI：

  10.1021/jo990992v

文献信息

• From Highly Enantioselective Monomeric Catalysts to Highly Enantioselective Polymeric Catalysts:  Application of Rigid and Sterically Regular Chiral Binaphthyl Polymers to the Asymmetric Synthesis of Chiral Secondary Alcohols
  作者：Wei-Sheng Huang、Qiao-Sheng Hu、Lin Pu

  DOI：10.1021/jo990992v

  日期：1999.10.1

  A 1,1'-binaphthyl-based polymeric chiral catalyst with the most general enantioselectivity for the alkylzinc addition to a broad range of aldehydes has been obtained. This polymer can be easily recovered, and the recycled polymer shows the same catalytic properties as the original polymer. A highly enantioselective catalytic diphenylzinc addition to aldehydes has also been achieved by using the chiral binaphthyl monomer and polymer catalysts. Particularly, the excellent enantioselectivity observed for the addition of diphenylzinc to aromatic aldehydes allows the preparation of optically active diaryl carbinols that are synthetically useful but difficult to access by asymmetric catalysis. A novel asymmetric reduction of ketones catalyzed by the mono- and polybinaphthyl zinc complexes has been discovered. Our work on the asymmetric organozinc addition to aldehydes and the asymmetric reduction of ketones catalyzed by the zinc complexes of chiral binaphthyl monomer (R)-12 and polybinaphthyl (R)-43 has not only provided new methods to prepare optically active secondary alcohols but also demonstrated that incorporation of an enantioselective monomeric catalyst into a rigid and sterically regular polymer structure could almost completely preserve the catalytic properties of the monomeric catalyst. This strategy may find general application in converting existing highly enantioselective monomer catalysts into polymer catalysts of similar enantioselectivity provided that the catalytically active species of the monomer catalysts contain only the monomeric units rather than the aggregates of the monomers. By using this strategy, it is possible to overcame the drawbacks associated with the traditional approach to preparing polymeric chiral catalysts where the microenvironments of the catalytic sites in the polymers are often significantly altered from those in the monomeric catalysts due to the flexible and sterically irregular polymer chains.