(1S,2S,3S)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate | 1153604-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,3S)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate
• 英文别名: [(1S,2S,3S)-1-cyclohexyl-3-hydroxy-2,4-dimethylpentyl] cyclohexanecarboxylate
• CAS: 1153604-99-9
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: MXMOYHVPPFYPOB-ZYSHUDEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环己烷基甲醛 、 syn-1-cyclohexyl-1-hydroxy-2,4-dimethylpentan-3-one 在 titanium(IV) tetrabutoxide 、 R-BINOL 、 辛可宁 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 rac-(1R,2R,3R)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate 、 (1S,2R,3S)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate 、 rac-(1R,2S,3R)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate 、 (1S,2S,3S)-1-cyclohexyl-3-hydroxy-2-methyl-4-methylpentyl cyclohexanecarboxylate
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635