3-methoxy-6-methyl-1-(trimethylsilyloxy)-2,6-cyclohexadiene | 426835-03-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-methoxy-6-methyl-1-(trimethylsilyloxy)-2,6-cyclohexadiene
• 英文别名: 3-methoxy-6-methyl-2-cyclohexenone trimethylsilyl enol ether；[(5-Methoxy-2-methylcyclohexa-1,5-dien-1-yl)oxy](trimethyl)silane；(5-methoxy-2-methylcyclohexa-1,5-dien-1-yl)oxy-trimethylsilane
• CAS: 426835-03-2
• 化学式: C₁₁H₂₀O₂Si
• 分子量: 212.364
• InChiKey: XMTFUPJXXGRXGE-UHFFFAOYSA-N

物化性质

• 沸点：
  270.4±40.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-6-methyl-1-(trimethylsilyloxy)-2,6-cyclohexadiene 在 铁粉 manganese(IV) oxide 、 吡啶-2,6-二甲酸 、 ammonium cerium(IV) nitrate 、 溴 作用下， 以 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2-bromo-3-methoxy-6-methyl-para-benzoquinone
  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：

  三甲基氯硅烷 、 3-methoxy-6-methyl-2-cyclohexenone 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 3-methoxy-6-methyl-1-(trimethylsilyloxy)-2,6-cyclohexadiene
  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 [1′-14C]Ubiquinone-2, [1′-14C]-5-Demethoxy-5-hydroxyubiquinone-2, and [1′-14C]-5-Demethoxyubiquinone-2
  作者：Anita van der Klei、Robertus L. P. de Jong、Johan Lugtenburg、Aloysius G. M. Tielens

  DOI：10.1002/1099-0690(200209)2002:17<3015::aid-ejoc3015>3.0.co;2-g

  日期：2002.9
• 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.