2-bromo-3-methoxy-8aα-methyl-4a,5,8,8a-tetrahydro-5α,8α-methano-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-methoxy-8aα-methyl-4a,5,8,8a-tetrahydro-5α,8α-methano-1,4-naphthoquinone
• 英文别名: (1S,2R,8R)-4-bromo-5-methoxy-2-methyltricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione
• 化学式: C₁₃H₁₃BrO₃
• 分子量: 297.148
• InChiKey: IPLREKWVSHYOQQ-UDXRAFPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3-methoxy-8aα-methyl-4a,5,8,8a-tetrahydro-5α,8α-methano-1,4-naphthoquinone 在 马来酸酐 、 三正丁基氢锡 、 sodium methylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 10.0h， 生成 辅酶Q10
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers

  摘要：

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.

  DOI：

  10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8
• 作为产物：
  描述：

  2,4-二溴-3-甲氧基-6-甲基苯酚 在 吡啶-2,6-二甲酸 、 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.0h， 生成 2-bromo-3-methoxy-8aα-methyl-4a,5,8,8a-tetrahydro-5α,8α-methano-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers

  摘要：

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.

  DOI：

  10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8

文献信息

• Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers
  作者：Rutger B. Boers、Peter Gast、Arnold J. Hoff、Huub J. M. de Groot、Johan Lugtenburg

  DOI：10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8

  日期：2002.1

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.