(4S,5R,6R)-2,4,6,8-Tetramethyl-5-trimethylsilanyloxy-nona-1,7-dien-3-one | 142405-72-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4S,5R,6R)-2,4,6,8-Tetramethyl-5-trimethylsilanyloxy-nona-1,7-dien-3-one
• CAS: 142405-72-9
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: TYFIVYSUKBOPFT-IIAWOOMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 (S,R)-2,4-Dimethylpent-3-enal 、 (endo-methyl-2 bicyclo<2.2.1>heptene-5) yl-2 ethyl cetone 生成 (4S,5R,6R)-2,4,6,8-Tetramethyl-5-trimethylsilanyloxy-nona-1,7-dien-3-one 、 (4S,5R,6S)-2,4,6,8-Tetramethyl-5-trimethylsilanyloxy-nona-1,7-dien-3-one
  参考文献：
  名称：

  Endo-2-methyl-bicyclo[2.2.1]-hept-5enyl ethyl ketone: an useful and highly stereoselective synthon for aldol reactions

  摘要：

  An excellent aldehyde diastereofacial selectivity has been observed during the aldol condensation between the lithium enolate of endo-2-methyl-bicyclo[2.2.1]-hept-5-enyl ethyl ketone 1 and a variety of alpha-methyl chiral aldehydes. 2-Aryl- and 2-vinyl-propionaldehyde gave rise to the predicted syn, syn "Felkin-Anh" diastereoisomers. In contrast beta-alkoxy or beta-silyloxy alpha-methyl aldehydes lead to the syn, anti aldols arising from an apparent chelation control.

  DOI：

  10.1016/s0040-4039(00)92225-1