2-(9-hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone | 77712-32-4

• 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-(9-hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
• 英文别名: idebenone；6-(9-Hydroxynonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone；2-(9-hydroxynonyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 77712-32-4
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: RPWNJDZWEGLYKY-UHFFFAOYSA-N

物化性质

• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 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 dipotassium peroxodisulfate 、 ammonium cerium (IV) nitrate 、 silver nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(9-hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
  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

• A facile synthesis of 1,4-benzoquinones having a hydroxyalkyl side chain.
  作者：GIICHI GOTO、KAYOKO OKAMOTO、TETSUYA OKUTANI、ISUKE IMADA

  DOI：10.1248/cpb.33.4422

  日期：——

  6-(ω-Hydroxyalkyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinones (3) and 6-(ω-acetoxyalkyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinones (26) having various carbon numbers (n) of the side chain were synthesized by the Friedel-Crafts coupling of 3, 4, 5-trimethoxytoluene (4) and ω-acetoxyalkanoyl chlorides (5) as a key step. The Fremy's salt oxidation or the salcomine-catalyzed oxidation of 6-(ω-hydroxyalkyl)-2, 3-dimethoxy-5-methylphenols (25) and their acetates (24), the key intermediates of the process, gave rise to 3 and 26, respectively, in good yields. The described method provides a good yield of the 1, 4-benzoquinones and is suitable for the synthesis of other quinonyl analogs. The effect on lipid peroxidation in canine brain homogenate of the 1, 4-benzoquinones (3) having various carbon numbers (n) of the side chain was studied. Among the compounds tested, 3 having a carbon number in the range of n=9-13 showed rather strong antioxidant activity.

  6-(ω-羟基烷基)-2,3-二甲氧基-5-甲基-1,4-苯醌(3)和6-(ω-乙酰氧基烷基)-2,3-二甲氧基-5-甲基-1,4-苯醌(26)具有不同的侧链碳数(n)，通过Friedel-Crafts耦合反应合成了3,4,5-三甲氧基甲苯(4)和ω-乙酰氧基烷酰氯(5)的关键步骤。Frémy盐氧化或水合氯化锡-催化氧化6-(ω-羟基烷基)-2,3-二甲氧基-5-甲基苯酚(25)及其乙酸盐(24)，该过程的关键中间体，分别以良好产率得到了3和26。所述方法提供了1,4-苯醌的高产率，并适用于其他醌类似物的合成。研究了1,4-苯醌(3)对犬脑匀浆中脂质过氧化的影响，具有不同的侧链碳数(n)。在测试的化合物中，n=9-13的3表现出相当强的抗氧化活性。
• AgNO₃-catalyzed decarboxylative cross-coupling reaction: an approach to coenzyme Q
  作者：Wan-Yue Luo、Bin Lu、Yong-Fu Qiu、Rong-Ye Zhou、Yong-Jing He、Jin Wang

  DOI：10.1039/d0nj01497d

  日期：——

  An efficient and general method for the synthesis of coenzyme Q compounds through the activation of the 1,4-benzoquinone Csp2–H bond has been developed. This C–C bond formation reaction proceeds readily in an open flask by the direct cross-coupling reaction of coenzyme Q0 with commercially available aliphatic carboxylic acids utilizing AgNO3 as a catalyst and K2S2O8 as an oxidant in aqueous solution

  通过激活1,4-苯醌C sp 2 -H键，已开发出一种有效且通用的合成辅酶Q化合物的方法。通过开放式辅酶Q 0与市售脂肪族羧酸的直接交联反应，利用水溶液中的AgNO 3和K 2 S 2 O 8作为氧化剂，这种C-C键形成反应易于进行。该自由基反应在操作上简单并且适合于克级合成。
• Quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04559177A1

  公开（公告）日：1985-12-17

  A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.

  一种化合物的化学式：##STR1## 其中m是11至22的整数；R.sub.1是具有1至4个碳原子的烷基；R.sub.2是氢，具有1至4个碳原子的烷基或具有1至8个碳原子的羧酸酰基。这些化合物具有药理活性，如降压、组织代谢刺激、免疫调节和溶酶体膜稳定活性，并抑制SRS-A的产生，可用作心力衰竭治疗、脑循环障碍治疗、免疫调节剂和抗过敏药物。
• 2,3-Dialkoxy-1,4-quinone derivatives; method of producing 1,4-quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0021841A2

  公开（公告）日：1981-01-07

  A compound of the general formula: wherein m is an integer of 10 to 21; R1 is lower alkyl having 1 to 4 carbon atoms; B is a -CH2- or-CO- group, when B is-CH2-, R2 is hydrogen, lower alkyl having 1 to 4 carbon atoms or lower acyl having 1 to 8 carbon atoms, and when B is -CO-, R2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immunoregulatory, lysosomal membrane stablizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immunoregulatorand antiallergic drug. A compound of the general formula: [wherein each R3 is lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, or two R3's taken together represent -CH =CH-CH =CH-; n is O or an integer of 1 to 20 and when n is 1 to 20, A is -CH2-, or -CO- and Z is CH2OH, acyloxymethyl having 2 to 11 carbon atoms, esterified or unesterified carboxyl having 1 to 5 carbon atoms, lower alkoxymethyl having 2 to 5 carbon atoms, silyloxymethyl having 4 to 7 carbon atoms or acetalmethyl having 3 to 8 carbon atoms; when n is O, -A(CH2)n-Z is (wherein - is 0 or an integer of 1 to 12) and Z is H] can be produced with advantage for commercial-scale production by oxidising a compound of the general formula: [wherein X1 or X2 is hydroxyl or amino, with the other being H or an esterified hydroxyl group having 1 to 8 carbon atoms or etherified hydroxyl group having 2 to to 8 carbon atoms; the other symbols are as defined above] with oxygen or air in the presence of a transition metal complex compound.

  通式如下的化合物 其中 m 是 10 至 21 的整数；R1 是具有 1 至 4 个碳原子的低级烷基；当 B 为-CH2-时，R2 为氢、具有 1 至 4 个碳原子的低级烷基或具有 1 至 8 个碳原子的低级酰基；当 B 为-CO-时，R2 为氢或具有 1 至 4 个碳原子的低级烷基、具有降血压、促进组织代谢、免疫调节、稳定溶酶体膜和抑制 SRS-A 生成等药物活性，可用作治疗心力衰竭、脑循环障碍、免疫调节和抗过敏药物。通式如下的化合物 [其中每个 R3 是具有 1 至 4 个碳原子的低级烷基或具有 1 至 4 个碳原子的低级烷氧基，或两个 R3 共同代表-CH =CH-CH =CH-；n 是 O 或 1 至 20 的整数，当 n 为 1 至 20 时，A 是-CH2-、 或-CO-，Z 是 CH2OH、具有 2 至 11 个碳原子的酰氧基甲基、具有 1 至 5 个碳原子的酯化或未酯化羧基、具有 2 至 5 个碳原子的低级烷氧基甲基、具有 4 至 7 个碳原子的硅氧基甲基或具有 3 至 8 个碳原子的乙缩醛甲基；当 n 是 O 时，-A(CH2)n-Z 是 (其中 - 为 0 或 1 至 12 的整数），Z 为 H]，可通过氧化通式如下的化合物生产，具有商业规模生产的优势： [其中 X1 或 X2 为羟基或氨基，另一个为 H 或具有 1 至 8 个碳原子的酯化羟基或具有 2 至 8 个碳原子的醚化羟基；其他符号如上定义]，在过渡金属复合物存在下，与氧气或空气氧化。
• Medicinal composition for treatment of allergic diseases
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0038674A1

  公开（公告）日：1981-10-28

  A mammal suffering from allergic disease due to SRS-A, such as skin symptoms, asthma, rhinitis, etc. is remedied by administering to said mammal an effective amount of a compound of the formula: wherein R is methoxy or methyl, or two R's taken together represent -CH =CH-CH =CH- n is an integer of 4 to 22.

  向患有 SRS-A 引起的过敏性疾病（如皮肤症状、哮喘、鼻炎等）的哺乳动物施用有效量的式化合物，可缓解其症状： 其中 R 是甲氧基或甲基，或两个 R 共同代表-CH =CH-CH =CH- n 是 4 至 22 的整数。