(2,5-bis(hexyloxy)phenyl)boronic acid | 202798-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2,5-bis(hexyloxy)phenyl)boronic acid
• 英文别名: 2,5-dihexyloxyphenylboronic acid；(2,5-Dihexoxyphenyl)boronic acid
• CAS: 202798-01-4
• 化学式: C₁₈H₃₁BO₄
• 分子量: 322.253
• InChiKey: WKMZNKSMFRWSNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,5-bis(hexyloxy)phenyl)boronic acid 在 正丁基锂 、 溴 、 sodium hydroxide 、 sodium sulfite 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 苯 为溶剂， 反应 69.16h， 生成 sodium (4-bromo-2,5-bis(hexyloxy)phenyl)trihydroxyborate
  参考文献：
  名称：

  Aryl Trihydroxyborate Salts: Thermally Unstable Species with Unusual Gelation Abilities

  摘要：

  A series of aryl trihydroxyborate salts were synthesized and found to form gels in benzene. The compounds were thermally unstable and readily underwent protodeboronation in solution and the solid state. Gelation could be induced without decomposition via sonication. Subsequent characterization studies revealed an unusual dependence of gel properties on alkyl chain length.

  DOI：

  10.1021/jo201353j
• 作为产物：
  描述：

  溴羟基喹啉 在 正丁基锂 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 (2,5-bis(hexyloxy)phenyl)boronic acid
  参考文献：
  名称：

  溶剂的化学潜力：合理化宾客关系的关键因素

  摘要：

  吸引力：在二氯甲烷中用[La（hfa）3 dig]客体直接滴定三齿宿主受体L时，表观交换常数 随形成的络合物[La（hfa）3 L]的数量呈指数增加。这怎么可能？

  DOI：

  10.1002/chem.201703184

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.
• A Highly General Catalyst for the Enantioselective Reaction of Aldehydes with Diethylzinc
  作者：Wei-Sheng Huang、Qiao-Sheng Hu、Lin Pu

  DOI：10.1021/jo971985e

  日期：1998.3.1