2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone | 89048-58-8

• 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
• 英文名称: 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone
• 英文别名: 2,3-dimethoxy-5-methyl-6-(morpholin-4-ylmethyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 89048-58-8
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: VUFLXIUJQQEESQ-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  440.7±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)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone 生成 2,3-dimethoxy-5-methyl-6-(morpholin-4-ylmethyl)cyclohexa-2,5-diene-1,4-dione;hydrochloride
  参考文献：
  名称：

  TERAO, SHINJI;OKAZAKI, HISAYOSHI;IMADA, ISUKE

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 ammonium cerium (IV) nitrate 、 氢溴酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone
  参考文献：
  名称：

  N-杂环基取代的辅酶Q类似物的高效合成和抗氧化活性。

  摘要：

  通过在无金属条件下用一系列胺12对溴甲基化醌11进行N-烷基化，开发了一种有效合成C-5杂环基取代的辅酶Q类似物的新策略。评估了这些辅酶Q类似物的体外抗氧化活性，并通过DPPH分析将其与市售抗氧化剂辅酶Q10进行了比较。发现所有这些N-杂环基取代的辅酶Q类似物均表现出良好的抗氧化剂性能，并且可用作抗氧化应激的有效抗氧化剂。

  DOI：

  10.1016/j.bioorg.2016.08.008

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。
• Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues
  作者：Jin Wang、Fei Xia、Wen-Bin Jin、Jin-Yan Guan、Hang Zhao

  DOI：10.1016/j.bioorg.2016.08.008

  日期：2016.10

  efficient synthesis of C-5 heterocyclyl substituted Coenzyme Q analogues was developed by N-alkylation of bromomethylated quinone 11 with a series of amines 12 under metal-free conditions. In vitro antioxidant activities of these Coenzyme Q analogues were evaluated and compared with commercial antioxidant Coenzyme Q10 by employing DPPH assay. All these N-heterocyclyl substituted Coenzyme Q analogues are

  通过在无金属条件下用一系列胺12对溴甲基化醌11进行N-烷基化，开发了一种有效合成C-5杂环基取代的辅酶Q类似物的新策略。评估了这些辅酶Q类似物的体外抗氧化活性，并通过DPPH分析将其与市售抗氧化剂辅酶Q10进行了比较。发现所有这些N-杂环基取代的辅酶Q类似物均表现出良好的抗氧化剂性能，并且可用作抗氧化应激的有效抗氧化剂。
• Benzoquinone derivatives and production thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04526719A1

  公开（公告）日：1985-07-02

  A novel benzoquinone derivative of the general formula: ##STR1## [wherein R.sub.1 and R.sub.2 are the same or different and each is methyl or methoxy; n is an integer of 0 to 21; m is 0 or 1, Z is a group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen or an alkyl group which may optionally be substituted or, R.sub.3 and R.sub.4 together with the adjacent nitrogen atom form a morpholino group), a group of the formula: --COR.sub.5 (wherein R.sub.5 is an .alpha.-amino acid residue or a substituted or unsubstituted glucosamine residue), a group of the formula: ##STR3## (wherein R.sub.6 is a divalent hydrocarbon group of 1 to 3 carbon atoms), a group of the formula: ##STR4## (wherein R.sub.6 has the same meaning as defined above) or a group of the formula: --CH.dbd.CH.sub.l --COR.sub.7 (wherein l is an integer of 1 to 4 and R.sub.7 is hydroxy, methoxy or methyl)] has protocollagen-proline hydroxylase inhibiting activity, collagen biosynthesis inhibiting activity and 5-lipoxygenase suppressant activity, and is useful for the prevention and treatment of such diseases as pulmonary fibrosis, hepatocirrhosis, nephrosclerosis, arteriosclerosis, scleroderma, myelofibrosis and chronic arthritis or for the prevention and treatment of asthma, allergic rhinitis, urticaria, etc.

  通用公式的一种新的苯醌衍生物：##STR1## [其中R.sub.1和R.sub.2相同或不同，每个都是甲基或甲氧基；n为0至21的整数；m为0或1，Z是以下式的一组：##STR2## （其中R.sub.3和R.sub.4相同或不同，每个是氢或可能被取代的烷基基团，或者R.sub.3和R.sub.4与相邻的氮原子一起形成吗啡基团），以下式的一组：--COR.sub.5（其中R.sub.5是α-氨基酸残基或取代或未取代的葡萄糖胺残基），以下式的一组：##STR3## （其中R.sub.6是1至3个碳原子的二价碳氢基团），以下式的一组：##STR4## （其中R.sub.6与上述定义相同），或以下式的一组：--CH.dbd.CH.sub.l --COR.sub.7（其中l为1至4的整数，R.sub.7为羟基、甲氧基或甲基）具有原胶原脯氨酸羟化酶抑制活性、胶原合成抑制活性和5-脂氧合酶抑制活性，并且对于预防和治疗肺纤维化、肝硬化、肾硬化、动脉硬化、硬皮病、骨髓纤维化和慢性关节炎等疾病或预防和治疗哮喘、过敏性鼻炎、荨麻疹等疾病是有用的。
• Synthesis and antioxidant activities of Coenzyme Q analogues
  作者：Jin Wang、Shuo Li、Tao Yang、Jian Yang

  DOI：10.1016/j.ejmech.2014.09.042

  日期：2014.10

  2,3-dimethoxy-5-methyl-1,4-benzoquinones (Coenzyme Q) substituted at the C-6 position with various groups were designed and synthesized based on the Coenzyme Q10 as potent antioxidant. In vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidant Coenzyme Q10 employing DPPH assay. All these synthesized Coenzyme Q analogues are found to exhibit good antioxidant

  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。
• Efficient synthesis of 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone hydrochloride
  作者：Jin Wang、Teng-huo-sheng Liao、Jian Yang

  DOI：10.1515/znb-2014-0208

  日期：2015.4.1

  The title compound (5) was prepared by a reaction sequence starting from 2,3,4,5-tetramethoxytoluene (1) via the Blanc reaction, oxidation and alkylation. The described method provides a good yield of the C-6 heterocyclic-substituted benzoquinone derivative and is suitable for the synthesis of other benzoquinone derivatives.

  标题：摘要 化合物标题（5）是通过从2,3,4,5-四甲氧基甲苯（1）开始的反应序列制备的，经过Blanc反应、氧化和烷基化。所描述的方法提供了C-6杂环取代苯醌衍生物的良好产率，并适用于其他苯醌衍生物的合成。