辅酶 Q5 | 4370-61-0

• 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 Q5
• 中文别名: 苯,[1-(二乙氧基甲基)乙烯基]-；辅酶Q5
• 英文名称: ubiquinone (25)
• 英文别名: Ubiquinone 25；2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]cyclohexa-2,5-diene-1,4-dione
• CAS: 4370-61-0
• 化学式: C₃₄H₅₀O₄
• 分子量: 522.769
• InChiKey: NYFAQDMDAFCWPU-UVCHAVPFSA-N

物化性质

• 沸点：
  637.9±55.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  辅酶 Q5 在 sodium hydroxide 、 维生素 C 作用下， 以 乙醇 为溶剂， 生成 ubiquinol-5
  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 盐酸 、 正丁基锂 、 二氯二茂锆 、 ammonium cerium(IV) nitrate 、 三苯基膦 、 nickel dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 3.25h， 生成 辅酶 Q5
  参考文献：
  名称：

  利用Ni（0）催化快速获得CoQ n，维生素K 1和K 2以及相关的烯丙基对苯二酚的途径

  摘要：

  催化量的Ni（0）介导的乙烯基丙氨酸与氯甲基化对醌之间的偶联反应直接导致烯丙基化产物，包括辅酶Q以及维生素K 1和K 2。

  DOI：

  10.1016/s0040-4020(97)10222-8

文献信息

• Ein neuer synthetischer Zugang zu Ubichinonen
  作者：August Rüttimann、Peter Lorenz

  DOI：10.1002/hlca.19900730404

  日期：1990.6.20

  A New Synthetic Route to Ubiquinones

  合成泛醌的新途径
• Regio- and stereoselective synthesis of coenzymes Qn (n = 2-10), vitamin K, and related polyprenylquinones
  作者：Yoshinori Naruta

  DOI：10.1021/jo01309a006

  日期：1980.10
• An expeditious route to CoQn, vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis
  作者：Bruce H. Lipshutz、Sung-kyu Kim、Paul Mollard、Kirk L. Stevens

  DOI：10.1016/s0040-4020(97)10222-8

  日期：1998.2

  Coupling reactions between vinylalanes and chloromethylated para-quinones, mediated by catalytic amounts of Ni(0), lead directly to allylated products, including coenzyme Q, and vitamins K1 and K2.

  催化量的Ni（0）介导的乙烯基丙氨酸与氯甲基化对醌之间的偶联反应直接导致烯丙基化产物，包括辅酶Q以及维生素K 1和K 2。
• The Surprisingly High Reactivity of Phenoxyl Radicals
  作者：M. Foti、K. U. Ingold、J. Lusztyk

  DOI：10.1021/ja00100a005

  日期：1994.10

  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.