2-(1-Hydroxy-2-phenyl-propyl)-5-methoxy-[1,4]benzoquinone | 133706-79-3

• 分子结构分类: 有机化合物
• 英文名称: 2-(1-Hydroxy-2-phenyl-propyl)-5-methoxy-[1,4]benzoquinone
• 英文别名: 2-(1-Hydroxy-2-phenylpropyl)-5-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 133706-79-3
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: MVGIFPONKZKHDM-UHFFFAOYSA-N

物化性质

• 沸点：
  452.3±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3,4-二甲氧基苯基)-2-苯基丙醇 在 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以55%的产率得到2-(1-Hydroxy-2-phenyl-propyl)-5-methoxy-[1,4]benzoquinone
  参考文献：
  名称：

  A new easy access to quinones from iron porphyrin-catalysed oxidation of methoxyarenes by magnesium monoperoxyphthalate

  摘要：

  富电子的甲氧基芳烃在温和条件下以高产率（55–100%）被氧化为相应的对醌，这一反应通过在适量水溶性铁卟啉催化剂存在的条件下使用单过氧邻苯二甲酸镁实现；该反应还被用于合成甲氧嘌呤。

  DOI：

  10.1039/c39910000031

文献信息

• Iron porphyrin-catalyzed oxidation of 1,2-dimethoxyarenes: a discussion of the different reactions involved and the competition between the formation of methoxyquinones or muconic dimethyl esters
  作者：Isabelle Artaud、Khaled Ben-Aziza、Daniel Mansuy

  DOI：10.1021/jo00064a026

  日期：1993.6

  This paper describes the oxidation of an alpha,beta-diarylpropane lignin dimer model and other dimethoxyarenes by several iron porphyrin-based biomimetic systems. From l-(3,4-dimethoxyphenyl)-2-phenylpropanol (1), three types of products are identified: the 3,4-dimethoxybenzaldehyde derived from the C(alpha)-C(beta) cleavage of the propyl side chain and either quinones or muconic dimethyl esters resulting from oxidations at the level of the dimethoxyaryl group. The selectivity of the reaction is discussed with respect to the nature and reactivity of the high-valent iron-oxo species formed upon reaction of the oxidants, H2O2 or magnesium monoperoxyphthalate (MMP), with the iron porphyrins. Fe(TF5PP)CI-catalyzed oxidation of 1 by H2O2 in an aprotic medium (CH3CN/CH2Cl2), yields a clean ''lignin peroxidase-like'' reaction with selective formation of the aldehyde. In an aqueous buffered solution, MMP oxidation of para-substituted 1,2-dimethoxyarenes catalyzed by an iron tetrakis(pentafluorophenyl)-beta-tetrasulfonatoporphyrin, Fe(TF5PS4P), clearly depends on the electronic properties of the para-substituent. The reaction is selective for para-quinone formation in the case of an electron-releasing group and for muconic dimethyl ester formation in the case of an electron-withdrawing group.