ubiquinol-3 | 69422-80-6

• 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: ubiquinol-3
• 英文别名: ubiquinol (15)；2,3-dimethoxy-5-methyl-6-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,4-diol
• CAS: 69422-80-6
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: CJEFSXQNNAAJQZ-NXGXIAAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 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：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ubiquinol-3 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 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：

  [3-D3]-、[3-13C]-和[1,2-13C2]丙炔的合成及其在合成[5-D3-甲基]-、[5-13C-甲基]-中的用途， [5,6-13C2-2,5-环己二烯基]泛醌3

  摘要：

  三种选择性标记的丙炔在 3 位用氘或碳 13 制备，并在 1 和 2 位用碳 13 双重标记，通过来自相应标记或未标记的单硫代乙炔和硫酸二甲酯的烷基化反应。它们与 nBuLi 锂化得到相应的丙炔基锂衍生物，该衍生物与方酸二甲酯反应得到相应的炔丙醇。这些在对二甲苯中热解以提供[5-D3-甲基]-、[5-13C-甲基]-和[5,6-13C2-2,5-环己二烯基]泛醌。在BF3催化下将法呢基侧链引入到标记的醌上，得到[5-D3-甲基]-、[5-13C-甲基]-和[5,6-13C2-2,5-环己二烯基]泛醌 3（分别为 6c、6b、6a）。

  DOI：

  10.1002/(sici)1099-0690(200003)2000:5<723::aid-ejoc723>3.0.co;2-q
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 正丁基锂 、 吡啶-2,6-二甲酸 、 ammonium cerium(IV) nitrate 、 四甲基乙二胺 作用下， 以 水 、 乙腈 为溶剂， 生成 ubiquinol-3
  参考文献：
  名称：

  Synthesis of 1,2,3,4-Tetrahydroxybenzene from d-Glucose:  Exploiting myo-Inositol as a Precursor to Aromatic Chemicals

  摘要：

  DOI：

  10.1021/ja9840293

文献信息

• 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.
• Terao, Shinji; Shiraishi, Mitsuru; Kato, Kaneyoshi, Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 2909 - 2920
  作者：Terao, Shinji、Shiraishi, Mitsuru、Kato, Kaneyoshi、Ohkawa, Shigenori、Ashida, Yasuko、Maki, Yoshitaka

  DOI：——

  日期：——
• OPHTHALMIC SOLUTION FOR PROTECTING INTERNAL STRUCTURES OF THE EYEBALL AGAINST UV-A RAYS OR FOR THE TREATMENT OF KERATOCONUS WITH A TRANS-EPITHELIAL CROSS-LINKING TECHNIQUE
  申请人：Troisi Salvatore

  公开号：US20120121567A1

  公开（公告）日：2012-05-17

  An ophthalmic solution containing riboflavin and at least a compound chosen in the group composed of essential and conditionally essential amino acids, coenzyme Q, L-proline, glycine, lysine hydrochloride, L-leucine, L-arginine and compounds intended to stimulate the production of metalloproteinase MMP9 for the protection of internal structures of the eyeball against UV-A rays or for the treatment of keratoconus with a trans-epithelial cross-linking technique.
• US9192594B2
  申请人：——

  公开号：US9192594B2

  公开（公告）日：2015-11-24