rel-(2S,3S)-ethyl 2-allyl-3-methoxybutanoate | 142612-20-2

• 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: rel-(2S,3S)-ethyl 2-allyl-3-methoxybutanoate
• 英文别名: ethyl (2R)-2-[(1R)-1-methoxyethyl]pent-4-enoate
• CAS: 142612-20-2；142612-21-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: XCPPPXOJPPIVSL-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(dimethyl(phenyl)silyl)butanoic acid ethyl ester 在 1,8-双二甲氨基萘 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 rel-(2S,3S)-ethyl 2-allyl-3-methoxybutanoate
  参考文献：
  名称：

  Investigation of a model for 1,2-asymmetric induction in reactions of .alpha.-carbalkoxy radicals: a stereochemical comparison of reactions of .alpha.-carbalkoxy radicals and ester enolates

  摘要：

  The stereochemical course of reductions and allylations of alpha-carbalkoxy radicals with chiral centers at the beta-position are reported. Radicals without polar substituents, with alkoxyl or acetoxyl groups, and with hydroxyl groups at the beta-position were examined. Reactions showed selectivities ranging from low (50:50) to high (99:1). The results are discussed in terms of transition-state models that emphasize the importance of (1) allylic conformational analysis (minimization of A1,3 and A1,2 strain), (2) torisonal strain (minimization of eclipsed interactions), and (3) stereoelectronic effects.

  DOI：

  10.1021/jo00042a029