4,6-Bis-[(R)-1-(2,4-dihydroxy-phenyl)-ethyl]-benzene-1,3-diol | 134938-96-8

• 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: 4,6-Bis-[(R)-1-(2,4-dihydroxy-phenyl)-ethyl]-benzene-1,3-diol
• CAS: 134938-96-8
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: STVQCWGFWOLKAF-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  三聚乙醛 、 间苯二酚 在 盐酸 、 氘代甲醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 22.0h， 生成 Calix[4]resorcinarene 、 4,4'-(ethane-1,1-diyl)bis(benzene-1,3-diol) 、 、 4,6-Bis-[(R)-1-(2,4-dihydroxy-phenyl)-ethyl]-benzene-1,3-diol 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Host-guest chemistry. 27. Mechanisms of macrocycle genesis. The condensation of resorcinol with aldehydes

  摘要：

  The title reactions proceed in high yields without high dilution techniques as long as substituents allow hydrogen bonds between the phenolic units and do not lead to steric hindrance. Isomerization rates for three epimeric cyclophanes, including a hitherto undiscovered one, are obtained by least-squares fit with integrated rate equations. The buildup sequences of oligomers, polymers, and macrocycles are analyzed by numerical stepwise integration with 50 rate constants, based on the fit of time-concentration curves of seven identified structures that were followed by proton NMR. Macrocyclization is favored by the following: (a) fast degradation of oligomers, (b) fast ring closure of tetramers, as well as (c) fast chain growth to these in comparison to ring opening. Homogeneous reaction conditions, here with methanol as solvent, are essential not only for the quantitative analyses, but also for the solubility of polymers in view of their degradation and for the observation of new stereoisomers. Molecular mechanics calculations with the CHARMm field and model considerations identify the factors responsible for the unique preference for cyclization over polymerization. Both hydrogen bonds between the phenolic units and 1.5 interactions between phenolic groups and the methyl substituent-stemming from the acetaldehyde-strongly favor folded conformers with small distances around d = 3.3-4.6 angstrom between the terminal reacting centers in comparison to stretched conformations with d = 12.2-18.3 angstrom.

  DOI：

  10.1021/jo00019a011