S-methyl (S)-2-(4-isobutylphenyl)thiopropionate

• 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: S-methyl (S)-2-(4-isobutylphenyl)thiopropionate
• 英文别名: S-methyl (2S)-2-[4-(2-methylpropyl)phenyl]propanethioate
• 化学式: C₁₄H₂₀OS
• 分子量: 236.378
• InChiKey: ARZSXCRVRVKSCN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S-甲基2-(4-异丁基苯基)硫代丙酸酯 在 (R)-1,1'-Bi-2-naphthol 、 四氯化锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.05h， 生成 S-methyl (S)-2-(4-isobutylphenyl)thiopropionate
  参考文献：
  名称：

  Deracemization of thiol esters of α-arylpropionic acids

  摘要：

  Racemic thiol esters of alpha-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1'-bi-2-naphthol/SnC1(4). Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00783-8

文献信息

• Deracemization of thiol esters of α-arylpropionic acids
  作者：Marco Clericuzio、Iacopo Degani、Stefano Dughera、Rita Fochi

  DOI：10.1016/s0957-4166(02)00783-8

  日期：2003.1

  Racemic thiol esters of alpha-arylpropionic acids were deracemized by a procedure which featured deprotonation with LDA or KHMDS, transformation into the TMS or TBDMS enol ethers, and enantioselective protonation of the silyl enol ethers using (R)-1,1'-bi-2-naphthol/SnC1(4). Oxidative hydrolysis of the enantiomerically enriched mixtures of thiol esters thus obtained yielded the (S)-enantiomers of ibuprofen and naproxen with ees up to 82%. (C) 2003 Elsevier Science Ltd. All rights reserved.