2-methoxy-5-(hydroxymethyl)-1,4-benzoquinone | 50827-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-5-(hydroxymethyl)-1,4-benzoquinone
• 英文别名: 2,5-Cyclohexadiene-1,4-dione, 2-(hydroxymethyl)-5-methoxy-；2-(hydroxymethyl)-5-methoxycyclohexa-2,5-diene-1,4-dione
• CAS: 50827-56-0
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: KTTQYVYUXZOVEN-UHFFFAOYSA-N

物化性质

• 保留指数：
  1540;1549;1562;1573

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-(hydroxymethyl)-1,4-benzoquinone 在 potassium acetate 作用下， 以 甲醇 为溶剂， 生成 2-甲氧基-1,4-萘醌
  参考文献：
  名称：

  藜芦油的合成研究。角度功能化AB系统的Diels-Alder方法。

  摘要：

  DOI：

  10.1021/jo00869a001
• 作为产物：
  描述：

  2-羟基-4-甲氧基苄醇 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 丙酮 为溶剂， 生成 2-methoxy-5-(hydroxymethyl)-1,4-benzoquinone
  参考文献：
  名称：

  与丝裂霉素有关的苯醌的合成及其抗肿瘤和抗菌活性。

  摘要：

  DOI：

  10.1021/jm00269a013

文献信息

• A new easy access to quinones from iron porphyrin-catalysed oxidation of methoxyarenes by magnesium monoperoxyphthalate
  作者：Isabelle Artaud、Khaled Ben Aziza、Claude Chopard、Daniel Mansuy

  DOI：10.1039/c39910000031

  日期：——

  Electron-rich methoxyarenes were oxidized with high yields (55–100%) and under mild conditions to the corresponding paraquinones by magnesium monoperoxyphthalate in the presence of catalytic amounts of a water-soluble iron porphyrin; the reaction was used to prepare methoxatin.

  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。
• Biomimetic Oxidation of Veratryl Alcohol with H₂O₂ Catalyzed by Iron(III) Porphyrins and Horseradish Peroxidase in Ionic Liquid
  作者：Anil Kumar、S. Chauhan、Nidhi Jain

  DOI：10.1055/s-2007-967951

  日期：2007.2

  a model compound for lignin substructures and its oxidation with H 2 O 2 catalyzed by iron(III) porphyrins and horseradish peroxidase (HRP) in ionic liquids has been described. Veratraldehyde and 2-hydroxymethyl-5-methoxy-2,5-cyclohexadiene-1,4-dione were the two major products of the oxidation of veratryl alcohol at room temperature. The iron(III) porphyrin or HRP immobilized in ionic liquids showed

  3,4-二甲氧基苄醇（藜芦醇）是木质素亚结构的模型化合物，已经描述了在离子液体中由铁 (III) 卟啉和辣根过氧化物酶 (HRP) 催化的 H 2 O 2 氧化。藜芦醛和 2-羟甲基-5-甲氧基-2,5-环己二烯-1,4-二酮是藜芦醇在室温下氧化的两种主要产物。固定在离子液体中的铁 (III) 卟啉或 HRP 显示出更高的催化活性并且可以回收利用，这被认为是由于反应中生成的高价氧代铁 (IV) π-阳离子自由基中间体的稳定性。
• Asymmetric Diels–Alder chemistry based on a new chiral auxiliary for 1-hydroxy substituted dienes
  作者：Philip Garner、James T. Anderson、Regis A. Turske

  DOI：10.1039/b003713n

  日期：——

  A rationally designed chiral auxiliary for hydroxylated dienes results in stereocontrolled Diels–Alder cycloadditions under purely thermal conditions.

  一种理性设计的手性辅助剂用于羟基化二烯，在纯热条件下实现了立体选择性的Diels-Alder环加成反应。
• 2, 5-Bis-Diamine [1,4] Benzoquinone-Derivatives
  申请人：Bolognesi Maria Laura

  公开号：US20090093521A1

  公开（公告）日：2009-04-09

  Synthesis of 2,5-bis-diamine-[1,4]benzoquinonic derivatives having the general formula (I), products and intermediates of said synthesis; the synthesis involves the use of p-benzoquinones having the general formula (IX) and diamines having the general formula (XI).

  合成具有通式(I)的2,5-双胺-[1,4]苯醌衍生物，以及所述合成的产物和中间体；合成涉及使用具有通式(IX)的对苯醌和具有通式(XI)的双胺。
• 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.