2-(p-Methoxyphenyl)-propan-1,2-diol | 178180-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(p-Methoxyphenyl)-propan-1,2-diol
• 英文别名: 2-(4-methoxyphenyl)propane-1,2-diol；2-(4-Methoxy-phenyl)-propan-1,2-diol；α.β-Dioxy-β-(4-methoxy-phenyl)-propan；β-(4-Methoxy-phenyl)-propylenglykol；2-(4-Methoxyphenyl)propane-1,2-diol
• CAS: 178180-80-8
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: GNUVKNWVXJIZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-Methoxyphenyl)-propan-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 4-(4-methoxyphenyl)-4-methyl-1,3-oxathiolan-2-one
  参考文献：
  名称：

  高区域选择性钯催化 O,S 重排环状硫代碳酸酯

  摘要：

  这项工作描述了一种操作简单的环状 S-硫代碳酸酯的催化合成，具有可预测的区域选择性和良好的产率。该反应利用源自普遍存在的 1,2-二醇的底物进行原子经济的分子内重排，由廉价且简单的催化剂-配体系统催化。呈现的晶体结构清楚地证实了反应的区域选择性。

  DOI：

  10.1002/ejoc.201701181
• 作为产物：
  描述：

  1-异丙烯基-4-甲氧基苯 在 potassium sulfate 、 potassium hydrogensulfate 、 oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 以75%的产率得到2-(p-Methoxyphenyl)-propan-1,2-diol
  参考文献：
  名称：

  Reaktivit�t und Selektivit�t bei der Oxidation von Styrolderivaten, II. Untersuchungen zur Oxidation vonp-substituierten ?-Methylstyrolen

  摘要：

  The liquid phase oxidation of p-substituted (Br-, Cl-, t-Bu-, MeO-, CF3-) alpha-methylstyrenes and of alpha,p-dimethoxystyrene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125 degrees C. The product yields were determined gaschromatographically. The differences of the activation energies of the epoxide formation and the parallel reactions amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and concentration of olefine. The relative chain propagation constants k(p) (C=C) Were determined by competitive oxidation with cumene. The k(p)(C=C) values of p-substituted alpha-methylstyrenes can be correlated by the Hammett equation with both sigma and sigma(+) substituent constants.

  DOI：

  10.1002/prac.19963380147

文献信息

• Resolution of Diols via Catalytic Asymmetric Acetalization
  作者：Ji Hye Kim、Ilija Čorić、Chiara Palumbo、Benjamin List

  DOI：10.1021/ja512481d

  日期：2015.2.11

  A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent

  使用手性限制的亚氨基二磷酸催化剂，通过不对称缩醛化实现了二醇的高度对映选择性动力学拆分。该反应对叔醇的拆分非常有效，选择性因子高达 >300。值得注意的是，即使在选择性因素仅为中等的情况下，高度对映体丰富的二醇也是通过立体发散拆分非对映缩醛获得的。
• Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis
  作者：Martin Pawliczek、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1039/c7sc04854h

  日期：——

  Herein, we report the first alkylative kinetic resolution of vicinal alcohols realized by cooperative use of a chiral quaternary ammonium salt and an achiral borinic acid. In addition, a catalytic regioselective alkylation of a secondary alcohol in the presence of an unprotected primary one is presented, emphasizing the unique selectivity and potential of this ammonium borinate catalysis.

  在此，我们报告了通过手性季铵盐和非手性硼酸的协同使用实现的连位醇的第一次烷基化动力学拆分。此外，还介绍了在未保护的伯醇存在下仲醇的催化区域选择性烷基化，强调了这种硼酸铵催化的独特选择性和潜力。
• Tiffeneau, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 1183
  作者：Tiffeneau

  DOI：——

  日期：——
• A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes
  作者：Michael R. Witten、Eric N. Jacobsen

  DOI：10.1021/acs.orglett.5b01193

  日期：2015.6.5

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.
• Reaktivit�t und Selektivit�t bei der Oxidation von Styrolderivaten, II. Untersuchungen zur Oxidation vonp-substituierten ?-Methylstyrolen
  作者：Wladimir Suprun

  DOI：10.1002/prac.19963380147

  日期：——

  The liquid phase oxidation of p-substituted (Br-, Cl-, t-Bu-, MeO-, CF3-) alpha-methylstyrenes and of alpha,p-dimethoxystyrene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125 degrees C. The product yields were determined gaschromatographically. The differences of the activation energies of the epoxide formation and the parallel reactions amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and concentration of olefine. The relative chain propagation constants k(p) (C=C) Were determined by competitive oxidation with cumene. The k(p)(C=C) values of p-substituted alpha-methylstyrenes can be correlated by the Hammett equation with both sigma and sigma(+) substituent constants.