2,3-二甲氧基-5-(甲氧基甲基)-6-甲基环己-2,5-二烯-1,4-二酮 | 84056-01-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 2,3-二甲氧基-5-(甲氧基甲基)-6-甲基环己-2,5-二烯-1,4-二酮
• 英文名称: 2,3-dimethoxy-6-methoxymethyl-5-methyl-1,4-benzoquinone
• 英文别名: 2,3-dimethoxy-5-(methoxymethyl)-6-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 84056-01-9
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: MJEUJFDGAMPWLH-UHFFFAOYSA-N

物化性质

• 熔点：
  33-34 °C
• 沸点：
  360.4±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 盐酸 、 ammonium cerium (IV) nitrate 、 sodium 、 potassium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 2,3-二甲氧基-5-(甲氧基甲基)-6-甲基环己-2,5-二烯-1,4-二酮
  参考文献：
  名称：

  辅酶Q类似物的合成及抗氧化活性

  摘要：

  基于辅酶Q 10作为有效的抗氧化剂，设计并合成了一系列在C-6位被多个基团取代的2,3-二甲氧基-5-甲基-1,4-苯醌（辅酶Q）。对这些化合物的体外抗氧化活性进行了评估，并与采用DPPH测定的商业抗氧化剂辅酶Q 10进行了比较。发现所有这些合成的辅酶Q类似物均表现出良好的抗氧化活性。其中在C-6位置带有N-苯甲酰基哌嗪基团的化合物8b与辅酶Q 10相比，对DPPH自由基的抑制作用更强。所有这些结果表明辅酶Q类似物作为抗氧化应激的有效抗氧化剂的适用性。

  DOI：

  10.1016/j.ejmech.2014.09.042

文献信息

• Effects of 6-(.OMEGA.-substituted alkyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinones and related compounds on mitochondrial succinate and reduced nicotinamide adenine dinucleotide oxidase systems.
  作者：KAYOKO OKAMOTO、MUTSUKO MATSUMOTO、MASAZUMI WATANABE、MITSURU KAWADA、TETSUJI IMAMOTO、ISUKE IMADA

  DOI：10.1248/cpb.33.3745

  日期：——

  2, 3-Dimethoxy-5-methyl-1, 4-benzoquinones having an ω-hydroxyalkyl or ω-aminoalkyl group at the 6-position were synthesized. The effects of these compounds and related compounds on the respiratory system of ubiquinone-depleted mitochondrial preparations were investigated. The compounds with an alkyl side chain of 10 to 13 carbon atoms showed rather high restoration activity on antimycin-sensitive succinate oxidation in acetone-treated beef heart mitochondria. This activity was correlated with their partition coefficients. Among these compounds, 6-(10-hydroxydecyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (V-10, idebenone) was selected for further testing to determine its effect on the respiratory system of injured canine brain mitochondrial preparation, because this compound showed prominent activity in the system described above. When V-10 was added to acetone-treated canine brain mitochondria (A-CBM), antimycin- and KCN-sensitive succinate oxidation were restored to the level observed in the freeze-stored canine brain mitochondria (CBM). V-10 also restored the reduced nicotinamide adenine dinucleotide (NADH) oxidation of pentane-treated canine brain mitochondria and submitochondrial particles (P-CBM and P-CBSM). Metabolites (I-4, I-10) of V-10 in human and animals showed no restoration activity in either respiratory enzyme system.

  合成了在6位具有ω-羟烷基或ω-氨烷基的2, 3-二甲氧基-5-甲基-1, 4-苯醌。这些化合物及相关化合物对缺乏泛醌的线粒体制备的呼吸系统的影响进行了研究。具有10到13个碳原子的烷基侧链的化合物在醋酮处理的牛心线粒体中对抗霉素敏感的琥珀酸氧化表现出相当高的恢复活性。该活性与它们的分配系数相关。在这些化合物中，6-(10-羟基癸基)-2, 3-二甲氧基-5-甲基-1, 4-苯醌（V-10，艾苯酮）被选中进行进一步测试，以确定其对受损犬脑线粒体制备的呼吸系统的影响，因为该化合物在上述系统中表现出显著活性。当V-10被添加到醋酮处理的犬脑线粒体（A-CBM）时，抗霉素和氰化物敏感的琥珀酸氧化恢复到冷冻保存的犬脑线粒体（CBM）所观察到的水平。V-10还恢复了五烷处理的犬脑线粒体和亚线粒体颗粒（P-CBM和P-CBSM）的还原型烟酰胺腺嘌呤二核苷酸（NADH）氧化。在人类和动物中，V-10的代谢物（I-4，I-10）在任一呼吸酶系统中均未显示出恢复活性。
• A Facile Synthesis of 2, 3-Dimethoxy-5-Methyl-1, 4-Benzoquinones
  作者：Jin Wang、Jian Yang、Rong-Guang Zhou、Bo Yang、Yuan-Shuang Wu

  DOI：10.3184/174751911x13099377293263

  日期：2011.7

  Several 2, 3-dimethoxy-5-methyl-1, 4-benzoquinones substituted at the C-6 position with alkoxy methyl groups were prepared by a reaction sequence starting from 2, 3, 4, 5-tetramethoxytoluene (alkoxy methyl) via a Blanc chloromethylation reaction, Williamson reaction and oxidation. The method provided a good yield of 2, 3-dimethoxy-5-methyl-1, 4-benzoquinones and is suitable for the synthesis of other benzoquinone analogues.

  以 2, 3, 4, 5-四甲氧基甲苯（烷氧基甲基）为起点，通过布兰克氯甲基化反应、威廉姆森反应和氧化反应，制备了多种 C-6 位被烷氧基甲基取代的 2, 3-二甲氧基-5-甲基-1, 4-苯醌。该方法提供了 2，3-二甲氧基-5-甲基-1，4-苯醌的高产率，并适用于合成其他苯醌类似物。
• Method of producing quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0058057A1

  公开（公告）日：1982-08-18

  A compound of the formula wherein R stands for an alkyl group having 1 to 22 carbon atoms and having at its terminal end a hydroxyl group which may be protected can be obtained with an industrial advantage by allowing a compound representable by the formula; to react with a peroxide of a carboxylic acid representable by the formula; RCOOH wherein R is of the same meaning as defined above, or with a peroxide of an acid anhydride of the carboxylic acid. A compound of the formula; wherein R2 stands for an alkyl group having 1 to 2 carbon atoms and having at its terminal end an optionally protected hydroxyl group, is a novel compound and has antifibrotic activity.

  式中的化合物 式中 R 代表具有 1 至 22 个碳原子的烷基，其末端具有可被保护的羟基，通过让式中的化合物与式中的羧酸的过氧化物反应，可获得具有工业优势的化合物； RCOOH 其中 R 的含义与上述定义相同，或与羧酸酸酐的过氧化物反应。 式中的化合物 其中 R2 代表具有 1 至 2 个碳原子并在其末端具有任选保护羟基的烷基，是一种新型化合物，具有抗纤维化活性。
• Single-step synthesis of idebenone from Coenzyme Q0 via free-radical alkylation under silver catalysis
  作者：Jin Wang、Shuo Li、Tao Yang、Jian Yang

  DOI：10.1016/j.tet.2014.10.017

  日期：2014.11

  Idebenone was synthesized directly by free-radical alkylation of 2,3-dimethyl-1,4-benzoquinone (Co-enzyme Q(0)) with commercially available 11-hydroxyundecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (CH3CN-H2O, 1:1) under mild condition in good yields (65%, based on Coenzyme Q(0)). The reaction is operationally simple and could be used in the preparation of other biologically Coenzyme Q analogues. (C) 2014 Elsevier Ltd. All rights reserved.
• WATANABE, MASAZUMI;IMADA, ISUKE
  作者：WATANABE, MASAZUMI、IMADA, ISUKE

  DOI：——

  日期：——