2-Hydroxymethyl-4-isopropyl-5-methyl-phenol | 130147-86-3

• 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: 2-Hydroxymethyl-4-isopropyl-5-methyl-phenol
• 英文别名: 2-(Hydroxymethyl)-5-methyl-4-propan-2-ylphenol
• CAS: 130147-86-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ZHJMJUAJPPTHEK-UHFFFAOYSA-N

物化性质

• 沸点：
  309.0±37.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hydroxymethyl-4-isopropyl-5-methyl-phenol 在 四氯化钛 作用下， 以 1,4-二氧六环 为溶剂， 以29%的产率得到4,10,16,22-Tetramethyl-5,11,17,23-tetra(propan-2-yl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9(27),10,12,15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
  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：

  聚合甲醛 、 3-甲基-4-异丙基苯酚 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.5h， 以45%的产率得到2-Hydroxymethyl-4-isopropyl-5-methyl-phenol
  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

文献信息

• Dissymmetric calix[4]arenes with C2 and C4 symmetry
  作者：Artur Wolff、Volker Boehmer、Walter Vogt、Franco Ugozzoli、Giovanni D. Andreetti

  DOI：10.1021/jo00309a001

  日期：1990.10