(S)-(+)-methyl 3-cyano-2-methyl-2-(4-methylphenyl)propionate | 133678-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(+)-methyl 3-cyano-2-methyl-2-(4-methylphenyl)propionate
• CAS: 133678-79-2
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: NIWVMILVTHMFIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-(+)-methyl 3-cyano-2-methyl-2-(4-methylphenyl)propionate 在 盐酸 、 氢氧化钾 作用下， 生成 (S)-(+)-2-methyl-2-(4-methylphenyl)butanedioic acid
  参考文献：
  名称：

  Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of .alpha.- and .beta.-cuparenones from a common optically active precursor.

  摘要：

  From a single chiron (R)-4, available with high enantiomeric purity (96%) by simple enzymatic hydrolysis (PLE) of a prochiral malonate, were prepared convenient precursors of the two enantiomers of alpha- and beta-cuparenones (1a,b and 2a,b). This versatile method also allows preparations of the enantiomer (S)-4 and dimethyl 2-methyl-2-p-tolylsuccinate ((S)-9a), as well as the new butyrolactones (R)-15, (R)-23, and (S)-25, the new but-3-enolide (S)-32, and cyclopentenones (S)-22 and (S)-30, all these compounds bearing an asymmetric quaternary carbon.

  DOI：

  10.1021/jo00038a041
• 作为产物：
  描述：

  (R)-(+)-methyl 3-hydroxy-2-methyl-2-(4-methylphenyl)propionate 在 吡啶 、 水 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 60.0h， 生成 (S)-(+)-methyl 3-cyano-2-methyl-2-(4-methylphenyl)propionate
  参考文献：
  名称：

  Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of .alpha.- and .beta.-cuparenones from a common optically active precursor.

  摘要：

  From a single chiron (R)-4, available with high enantiomeric purity (96%) by simple enzymatic hydrolysis (PLE) of a prochiral malonate, were prepared convenient precursors of the two enantiomers of alpha- and beta-cuparenones (1a,b and 2a,b). This versatile method also allows preparations of the enantiomer (S)-4 and dimethyl 2-methyl-2-p-tolylsuccinate ((S)-9a), as well as the new butyrolactones (R)-15, (R)-23, and (S)-25, the new but-3-enolide (S)-32, and cyclopentenones (S)-22 and (S)-30, all these compounds bearing an asymmetric quaternary carbon.

  DOI：

  10.1021/jo00038a041

文献信息

• Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of .alpha.- and .beta.-cuparenones from a common optically active precursor.
  作者：Jean Louis Canet、Antoine Fadel、Jacques Salaun

  DOI：10.1021/jo00038a041

  日期：1992.6

  From a single chiron (R)-4, available with high enantiomeric purity (96%) by simple enzymatic hydrolysis (PLE) of a prochiral malonate, were prepared convenient precursors of the two enantiomers of alpha- and beta-cuparenones (1a,b and 2a,b). This versatile method also allows preparations of the enantiomer (S)-4 and dimethyl 2-methyl-2-p-tolylsuccinate ((S)-9a), as well as the new butyrolactones (R)-15, (R)-23, and (S)-25, the new but-3-enolide (S)-32, and cyclopentenones (S)-22 and (S)-30, all these compounds bearing an asymmetric quaternary carbon.