(2S,3S,4R,5S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexanone | 767319-48-2

• 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: (2S,3S,4R,5S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexanone
• CAS: 767319-48-2
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: XAMIKXMRCHGQJL-SQJBMSRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexanone 在 吡啶 、 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R,3S,4R,5R,6S)-3-ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexyl ester
  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：

  (-)-(1Z,2S,3R,4R)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate 在 三正丁基甲氧基锡 作用下， 70.0 ℃ 、13.33 Pa 条件下， 反应 12.0h， 以84%的产率得到(2S,3S,4R,5S,6S)-3-Ethyl-3-hydroxy-2,4,6-trimethyl-5-((S)-1-phenyl-ethoxy)-cyclohexanone
  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