2-hydroxymethyl-3,4-propanophenol | 149385-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-hydroxymethyl-3,4-propanophenol
• 英文别名: 4-hydroxymethyl-5-indanol；4-(hydroxymethyl)-2,3-dihydro-1H-inden-5-ol
• CAS: 149385-33-1
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: HCLNZGJLKSBOOM-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  317.0±22.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-3,4-propanophenol 在 sodium periodate 作用下， 以 乙腈 为溶剂， 以63%的产率得到2,3-dihydrospiro[indene-4,2'-oxiran]-5(1H)-one
  参考文献：
  名称：

  芳香族化合物的分子复杂性：一种新颖的立体选择路线，生成三环[5.2.2.0 1,5 ]十一碳烯，三环[6.2.2.0 1,6 ]十二碳烯和[ n .3.3]丙环烷

  摘要：

  据报道，从简单的芳香族前体到官能化和取代的三环[5.2.2.0 1,5 ]十一碳烯，三环[6.2.2.0 1,6 ]十二碳烯以及[3.3.3]-和[4.3.3]丙炔的一般立体选择路线。该方法涉及用各种丙烯酸酯生成和环化环己二环2,4-二烯酮，然后处理所得的三环加合物，从而导致官能化的三环[5.2.2.0 1,5 ]十一碳烯和三环[6.2.2.0 1,6 ]十二碳烯具有β，γ-烯酮发色团。三环发色体系的光化学反应，然后进行还原性裂解，有效地进入了螺旋桨。

  DOI：

  10.1021/jo702168s
• 作为产物：
  描述：

  6-溴-5-茚醇 在 镍 氢氧化钾 、 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 2-hydroxymethyl-3,4-propanophenol
  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