2,5-环己二烯-1,4-二酮,2,3-二甲氧基-5-甲基-6-[(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-基]- | 1173-76-8

• 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
• 中文名称: 2,5-环己二烯-1,4-二酮,2,3-二甲氧基-5-甲基-6-[(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-基]-
• 英文名称: ubiquinone Q3
• 英文别名: ubiquinone 3；coenzyme Q3；2,3-dimethoxy-5-methyl-6-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)cyclohexa-2,5-diene-1,4-dione；2,3-Dimethoxy-5-methyl-6-farnesyl-benzochinon；2,5-Cyclohexadiene-1,4-dione, 2,3-dimethoxy-5-methyl-6-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-, (E,E)-；2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 1173-76-8
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: XREILSQAXUAAHP-NXGXIAAHSA-N

物化性质

• 沸点：
  526.8±50.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-环己二烯-1,4-二酮,2,3-二甲氧基-5-甲基-6-[(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-基]- 在 sodium hydroxide 、 维生素 C 作用下， 以 乙醇 为溶剂， 生成 ubiquinol-3
  参考文献：
  名称：

  The Surprisingly High Reactivity of Phenoxyl Radicals

  摘要：

  Rate constants have been measured in nonaqueous media for hydrogen atom abstraction by the phenoxyl radical from some biologically important phenols and related compounds. Although the thermochemistry for these reactions must be very similar to the thermochemistry for H atom abstraction from the same substrate by a peroxyl radical, the phenoxyl rate constants, k(5), are ca. 100-300 times greater than the (already well-known) peroxyl rate constants, k(1). For example, with alpha-tocopherol in benzene/di-tert-butyl peroxide (1:3, v/v) k(5)(293K) = 1.1 X 10(9) M(-1) s(-1) vs k(1)(303K) = 3.2 X 10(6) M(-1) s(-1) in a similar nonpolar medium, and with ubiquinol-10 in the same solvent mixture k(5)(293K) = 8.4 X 10(7) M(-1) s(-1), while the corresponding value for k(1) is 3.5 X 10(5) M(-1) s(-1). The greater reactivity of the phenoxyl radical has been traced to the fact that the Arrhenius preexponential factors are much larger than for the corresponding peroxyl radical reactions, i.e., A(5) similar to 10(2)A(1). For example, with alpha-naphthol log(A(5)/M(-1) s(-1)) = 8.9 and E(5) = 2.2 kcal/mol vs log(A(1)/M(-1) s(-1)) = 6.4 and E(1) = 1.7 kcal/mol. The preexponential factors for II-atom donors more reactive than alpha-naphthol are even greater; for example, with alpha-tocopherol in CH3CN/di-tert-butyl peroxide (1:2, v/v) log(A(5)/M(-1) s(-1)) = 10.0 and E(5) 2.0 kcal/mol, and with ubiquinol-0 in benzene/di-tert-butyl peroxide (1:3, v/v) log(A(5)/M(-1) s(-1)) = 10.5 and E(5) = 3.5 kcal/mol. The role that intermediate hydrogen-bonded complexes between the reacting radical and the phenolic hydrogen donor may play in these reactions is discussed, and it is pointed out that our results are likely to be relevant to in vivo radical chemistry.

  DOI：

  10.1021/ja00100a005
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 吡啶-2,6-二甲酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 2,5-环己二烯-1,4-二酮,2,3-二甲氧基-5-甲基-6-[(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-基]-
  参考文献：
  名称：

  Total synthesis of linear polyprenoids. 2. Improved preparation of the aromatic nucleus of ubiquinone

  摘要：

  DOI：

  10.1021/jo00226a028

文献信息

• METHOD OF PREPARATION OF STEREOSPECIFIC QUINONE DERIVATIVES
  申请人：Mehta Dilip S.

  公开号：US20150126763A1

  公开（公告）日：2015-05-07

  The description provides processes for the regio and stereospecific synthesis of polyprenylatedquinone derivatives, such as Vitamin K1, K2 and Ubiquinone, exploiting dithioacetals, especially 1,3-dithiane, mediated Umpolung chemistry which works along a new concept “Inhibiting resonance delocalization (IRD)” to overcome isomerization generated due to delocalization of allyliccarbanion on the π-electron cloud of an allylic systems by the conventional synthesis.

  该描述提供了多种聚戊二烯醌衍生物的区域和立体特异性合成过程，例如维生素K1、K2和辅酶Q，利用二硫代缩醛，特别是1,3-二硫代环戊烷，介导的Umpolung化学，该化学沿着一个新概念“抑制共振离域化（IRD）”工作，以克服由于烯丙基碳负离子在烯丙基体系的π电子云上的离域化而产生的异构化，这是传统合成无法解决的。
• 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。

• Ubichinone und verwandte Substanzen, XXIII1) Synthese von Chinonen mit neuen Kondensationsmitteln
  作者：Hirosada Sugihara、Marekichi Sasaki、Yutaka Kawamatsu、Hiroshi Morimoto

  DOI：10.1002/jlac.19727630113

  日期：1972.11.24

  Hydrochinone können mit isoprenoiden Alkoholen mit Hilfe von N-Sulfinylaminen kondensiert werden (Tab. 1). Nach dieser Methode lassen sich 6-Phytyl- (trans-5a), 6-Farnesyl-(trans-5b), 6-Geranyl- (trans-5c), 6-Neryl-2.3-dimethoxy-5-methyl-1.4-benzochinon (cis-5c) und 2.3.5-Trimethyl-6-phytyl-1.4-benzochinon (trans-6) sowie 2-Methyl-3-phytyl-1.4-naphthochinon (trans-7) synthetisieren. Der Reaktionsmechanismus

  氢醌酮类异戊二烯烯醇酯类Hilfe von N-亚磺胺基酮kendensiert werden（表1）。Nach Dieser Methode lassen sich 6-Pytyl-（trans - 5a），6-Farnesyl-（trans - 5b），6-Geranyl-（trans - 5c），6-Neryl-2.3-二甲氧基-5-甲基-1.4-苯并chin酮（顺式- 5C）UND 2.3.5三甲基-6-叶绿基1.4 benzochinon（反式- 6）sowie 2-甲基-3-叶绿基1.4 naphthochinon（反式- 7 synthetisieren）。这种机制与立体声音碟之间存在着很大的差异。。。。。。。。。。。。。。。。。。。。。。。。。。。。。