1,3-Dimethoxy-2-methyl-1-(trimethylsiloxy)-1,3-butadiene

• 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: 1,3-Dimethoxy-2-methyl-1-(trimethylsiloxy)-1,3-butadiene
• 英文别名: [(1E)-1,3-dimethoxy-2-methylbuta-1,3-dienoxy]-trimethylsilane
• 化学式: C₁₀H₂₀O₃Si
• 分子量: 216.352
• InChiKey: WOFDRPLWNTYVSV-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二溴对苯醌 、 1,3-Dimethoxy-2-methyl-1-(trimethylsiloxy)-1,3-butadiene 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 3-Bromo-5-hydroxy-7-methoxy-6-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-甲基-3-氧代丁酸甲酯 、 原甲酸三甲酯 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 生成 1,3-Dimethoxy-2-methyl-1-(trimethylsiloxy)-1,3-butadiene
  参考文献：
  名称：

  Synthesis of the Naphthoquinone Nucleus of Awamycin

  摘要：

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.

  DOI：

  10.1021/jo00119a018

文献信息

• Synthesis of the Naphthoquinone Nucleus of Awamycin
  作者：William R. Roush、D. Scott Coffey

  DOI：10.1021/jo00119a018

  日期：1995.7

  A synthesis of ketone 4, corresponding to the fully elaborated naphthoquinone nucleus of awamycin, is described. The synthesis involves the Diels-Alder reaction between diene 8 and quinone 9 to construct naphthoquinone 10, the coupling of bromide 15 and an ansa chain surrogate 17 via an aryllithium intermediate, and a late stage 1,4-addition of NaSMe to naphthoquinone 23 to afford the ketone 4.