Methyl 4-hydroxy-5-cyclohexylpent-2-enoate | 130255-29-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 4-hydroxy-5-cyclohexylpent-2-enoate
• 英文别名: (R),(E)-Methyl 5-cyclohexyl-4-hydroxypent-2-enoate；(S),(E)-Methyl 5-cyclohexyl-4-hydroxypent-2-enoate
• CAS: 130255-29-7；130323-23-8
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: QWYVQJYWESCBDQ-WSKFYRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate 、 环己基乙醛 在 哌啶 作用下， 以 乙腈 为溶剂， 反应 13.0h， 生成 Methyl 4-hydroxy-5-cyclohexylpent-2-enoate 、 (R),(E)-Methyl 5-cyclohexyl-4-hydroxypent-2-enoate
  参考文献：
  名称：

  Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog

  摘要：

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).

  DOI：

  10.1021/jo00006a017