6-bromo-2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-3,4-dimethylphenol | 149385-41-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 6-bromo-2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-3,4-dimethylphenol
• CAS: 149385-41-1
• 化学式: C₁₇H₁₉BrO₃
• 分子量: 351.24
• InChiKey: RRPMUCNNDGAABO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-bromo-2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-3,4-dimethylphenol 在 镍 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-3,4-dimethylphenol
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C4- and C2-symmetry. Synthesis, x-ray structures, conformational fixation, and proton NMR spectroscopic studies

  摘要：

  Six dissymmetric calix[4]arenes with C4 symmetry consisting of four 3,4-disubstituted phenolic units have been obtained by condensation of the respective 2- or 6-hydroxymethylated phenols. The regular incorporation of the phenolic units into the macrocycle was established on the basis of H-1 NMR spectra and in one case also by X-ray analysis. One example for a calixarene with C2-symmetry consisting of p-cresol and 3,4-dimethylphenol units in alternating sequence was also prepared. Calixarene 4a consisting of 3,4-dimethylphenol units shows a lower energy barrier (DELTAG(double dagger) = 13.4 kcal/mol) for the cone-to-cone inversion in CDCl3 than p-methylcalix[4]arene (DELTAG(double dagger) = 14.6 kcal/mol). The dissymmetric calixarenes 4 could be conformationally fixed by alkylation of the phenolic hydroxyl group. Due to the equivalence of all four phenolic units, mono- and 1,3-di-derivatives could be obtained in addition to tetra derivatives. A tetraester derivative in the cone conformation, like the parent calix[4]arene, crystallizes as a racemate. In solution these tetraester derivatives exist in a distorted cone conformation with C2 symmetry. Dynamic H-1 NMR spectra reveal an energy barrier of DELTAG(double dagger) = 13.3-13.4 kcal/mol for the C2-to-C2 interconversion with the C4-cone as transition state.

  DOI：

  10.1021/jo00067a040
• 作为产物：
  描述：

  3,4-二甲基苯酚 在 brominating reagent 作用下， 生成 6-bromo-2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-3,4-dimethylphenol
  参考文献：
  名称：

  Dissymmetric calix[4]arenes with C2 and C4 symmetry

  摘要：

  DOI：

  10.1021/jo00309a001