(1Z,5Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-((1S)-1-phenylethoxy)-5-((triethylsilyl)oxy)hept-5-en-1-yl isobutyrate | 767319-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1Z,5Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-((1S)-1-phenylethoxy)-5-((triethylsilyl)oxy)hept-5-en-1-yl isobutyrate
• 英文别名: [(2Z,4S,5R,6S,7Z)-4,6-dimethyl-5-[(1S)-1-phenylethoxy]-7-triethylsilyloxynona-2,7-dien-3-yl] 2-methylpropanoate
• CAS: 767319-52-8
• 化学式: C₂₉H₄₈O₄Si
• 分子量: 488.783
• InChiKey: QSELGNYDPNRMLX-XGQCXKJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1Z,5Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-((1S)-1-phenylethoxy)-5-((triethylsilyl)oxy)hept-5-en-1-yl isobutyrate 在 palladium on activated charcoal methyllithium lithium bromide 、 氢气 、 氯化铵 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 12.08h， 生成 (-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione
  参考文献：
  名称：

  First Asymmetric Synthesis of the Cyclohexanone Subunit of Baconipyrones A and B. Revision of Its Structure

  摘要：

  An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO2).

  DOI：

  10.1021/ol048988f
• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 、 (-)-(1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(1Z,5Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-3-((1S)-1-phenylethoxy)-5-((triethylsilyl)oxy)hept-5-en-1-yl isobutyrate
  参考文献：
  名称：

  First Asymmetric Synthesis of the Cyclohexanone Subunit of Baconipyrones A and B. Revision of Its Structure

  摘要：

  An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO2).

  DOI：

  10.1021/ol048988f

文献信息

• First Asymmetric Synthesis of the Cyclohexanone Subunit of Baconipyrones A and B. Revision of Its Structure
  作者：Māris Turks、M. Carmen Murcia、Rosario Scopelliti、Pierre Vogel

  DOI：10.1021/ol048988f

  日期：2004.9.1

  An asymmetric synthesis of the 3,5-dihydroxycyclohexanone subunit of baconipyrones A and B, as well as that of the hydroxydiketone subunit of baconipyrones C and D ((-)-(4S,6S)-4,6-dimethyl-5-hydroxynonan-3,7-dione), is described. Key steps include sulfur dioxide-induced additions of enoxysilanes to 1,3-dioxy-1,3-dienes, followed by retro-ene desulfitations (retro-ene elimination of SO2).