辅酶 Q2 | 606-06-4

• 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
• 中文名称: 辅酶 Q2
• 中文别名: 辅酶Q2；2,3-二甲氧基-5-甲基-香叶基-1,4-苯醌
• 英文名称: 2-[(E)-3,7-dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone
• 英文别名: coenzyme Q₂；ubiquinone-2；ubiquinone Q2；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 606-06-4；1339-63-5
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: SQQWBSBBCSFQGC-JLHYYAGUSA-N

物化性质

• 沸点：
  465.8±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL；乙醇：10mg/mL
• 物理描述：
  Solid
• 碰撞截面：
  174.3 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,3-二甲氧基-5-甲基-1,4-苯醌	2,3-Dimethoxy-5-methyl-1,4-benzoquinone	605-94-7	C9H10O4	182.176

反应信息

• 作为反应物：
  描述：

  辅酶 Q2 在 吡啶 、 sodium dithionite 、 水 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.17h， 生成 3-((E)-3,7-Dimethyl-octa-2,6-dienyl)-5,6-dimethoxy-2-methyl-4-triethylsilanyloxy-phenol
  参考文献：
  名称：

  Design, Synthesis, and Photochemical Properties of a Photoreleasable Ubiquinol-2:  A Novel Compound for Studying Rapid Electron-Transfer Kinetics in Ubiquinol-Oxidizing Enzymes

  摘要：

  The design and multistep convergent synthesis of the novel photoactive ubiquinol-benzoin adduct 1a,b has been accomplished. Optical spectra of the steady-state photolysis reactions showed a smooth conversion from 1a,b to 5,7-dimethoxy-2-phenylbenzofuran (13) and ubiquinol-2 with an isobestic point at 258 nm. HPLC analysis of the photoproducts was also consistent with the clean formation of the desired ubiquinol-2 (3) and the expected 5,7-dimethoxy-2-phenylbenzofuran (2). Transient photolysis at 355 nm was consistent with a rapid photolysis rate that exceeded the instrument response time (>10(6) s(-1)). Accordingly, the study of rapid electron-transfer events in ubiquinol oxidizing enzymes is now feasible. Furthermore, the synthetic methods developed herein will be of general application for the facile synthesis of a variety of photoreleasable substrates for studying rapid kinetic events in enzymatic reactions.

  DOI：

  10.1021/ja971079j
• 作为产物：
  描述：

  5-甲五倍子酚 在 palladium on activated charcoal 、 Amberlite IR 120-plus 、 四丁基硫酸氢铵 potassium nitrososulfonate 、 4 A molecular sieve 、 potassium tert-butylate 、 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， -70.0~80.0 ℃ 、999.92 Pa 条件下， 反应 163.5h， 生成 辅酶 Q2
  参考文献：
  名称：

  Synthesis of Crown Ethers Related to Ubiquinones

  摘要：

  用五个简单步骤从5-甲基吡咯卡酚中获得了冠醚，其中 ubiquinone-0（2,3-二甲氧基-5-甲基-1,4-苯醌）的两个甲氧基被寡聚乙二醇桥替代，整体产率为35-40%。在最终步骤中采用了Fremy盐氧化酚前体。通过对前述醌的环戊二烯加成物进行烯醇香豆烯基化以及随后的逆Diels-Alder反应，进一步开发了ubiquinone-2的冠醚类似物。2,2-二甲氧基-5-甲基苯基烯丙醚及相关冠醚的Claisen重排产生了ortho和para-烯丙基取代的酚（比例为3:1），随后被氧化生成bisnorubiquinone衍生物及其ortho-醌异构体。所有新化合物均通过高分辨率NMR和质谱进行表征。

  DOI：

  10.1055/s-1993-25945

文献信息

• Synthesis of ubiquinone and menaquinone analogues by oxidative demethylation of alkenylhydroquinone ethers with argentic oxide or ceric ammonium nitrat
  作者：L. Syper、K. Kloc、J. Mz.xl;lochowski

  DOI：10.1016/0040-4020(80)85034-4

  日期：1980.1

  It was found that alkenylhydroquinone ethers demethylated with argentic oxide or ceric ammonium nitrate in the presence of 2,4,6-pyridinetricarboxylic acid as a catalyst and afforded ubiquinone-2, menaquinone-2 and their analogs in yields of 53 to 89%. The new approach to the synthesis of starting alkenylhydroquinone ethers as well as 2,4,6-pyridinetricarboxylic acid and its derivatives has been reported

  发现在2,4,6-吡啶三甲酸作为催化剂的存在下，用氧化亚铁或硝酸铈铵对甲基化的烯基对苯二酚醚进行脱甲基，得到的泛醌2，甲萘醌2及其类似物的产率为53％至89％。已经报道了合成起始烯基氢醌醚以及2,4,6-吡啶三羧酸及其衍生物的新方法。
• DIHYDROOROTATE DEHYDROGENASE AS ANTIFUNGAL DRUG TARGET AND QUINAZOLINONE-BASED INHIBITORS THEREOF
  申请人：Oliver Jason David

  公开号：US20110160231A1

  公开（公告）日：2011-06-30

  A method of identifying an antifungal agent which targets a DHODH protein (alias PyrE, dihydroorotate dehydrogenase, EC: 1.3.99.11) of a fungus comprising contacting a candidate substance with a fungal DHODH protein and determining whether the candidate substance binds or modulates the DHODH protein, wherein binding or modulation indicates that the candidate substance is an antifungal agent. Specific examples concern Aspergillus fumigatus and Candida albicans DHODH proteins. DHODH inhibitors with a Quinazolinone core are also disclosed.

  一种识别靶向真菌DHODH蛋白（别名PyrE，二氢乳酸脱氢酶，EC：1.3.99.11）的抗真菌剂的方法，包括将候选物质与真菌DHODH蛋白接触，并确定候选物质是否结合或调节DHODH蛋白，其中结合或调节表明候选物质是抗真菌剂。具体示例涉及 曲霉菌 和 白念珠菌 DHODH蛋白。还公开了具有喹唑啉酮核心的DHODH抑制剂。
• New Efficient Synthesis of Ubiquinones
  作者：Paolo Bovicelli、Giorgio Borioni、Danilo Fabbrini、Maurizio Barontini

  DOI：10.1080/00397910701771066

  日期：2008.1.1

  Abstract A strategy for the ecofriendly and high‐yielding synthesis of ubiquinones starting from simple materials and using mild conditions is reported. CoQ1, CoQ2, CoQ3, and CoQ9 were prepared.

  摘要 报道了一种从简单材料开始、在温和条件下环境友好、高产合成泛醌的策略。制备 CoQ1、CoQ2、CoQ3 和 CoQ9。
• REGIOSELECTIVE POLYPRENYL REARRANGEMENT OF POLYPRENYL 2,3,4,5-TETRASUBSTITUTED PHENYL ETHERS PROMOTED BY BORON TRIFLUORIDE
  作者：Toyokichi Yoshizawa、Hatsunori Toyofuku、Koichi Tachibana、Toshio Kuroda

  DOI：10.1246/cl.1982.1131

  日期：1982.8.5

  ,3,5-trimethylphenols or 2,3-dimethoxy-5-methyl-6-polyprenylhydroquinones were obtained selectively by the BF3·OEt2 catalyzed polyprenyl rearrangement of polyprenyl 4-acetoxy-2,3,5-trimethylphenyl ethers or polyprenyl 2,3-dimethoxy-4-hydroxy-5-methylphenyl ethers.

  通过BF3·OEt2催化聚异戊二烯基4-乙酰氧基-2,3重排，选择性地获得4-乙酰氧基-6-聚异戊二烯基-2,3,5-三甲基苯酚或2,3-二甲氧基-5-甲基-6-聚异戊二烯基氢醌， 5-三甲基苯基醚或聚异戊二烯基 2,3-二甲氧基-4-羟基-5-甲基苯基醚。
• Radical-scavenging polyphenols: new strategies for their synthesis
  作者：Paolo Bovicelli

  DOI：10.1211/jpp.59.12.0013

  日期：2010.2.18

  New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxy-tyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.

  讨论了合成多酚的新策略，这些化合物具有抗氧化性质，存在于各种植物中。采用简单和环保的方法接近了不同类别的多酚的合成，包括存在于许多自然系统中的泛醌类多酚，其中涉及电子转移机制，羟基酪醇，是橄榄中酚类分数的主要成分，以及在植物界广泛分布的类黄酮。