(R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate | 133678-80-5

• 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: (R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate
• CAS: 133678-80-5
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: VVPJDMQONMZFHP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate 在 盐酸 、 Raney Nickel (W₂) 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 60.67h， 生成 (3S)-(+)-3-methyl-3-(4-methylphenyl)pentane-1,4-diol
  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)-(+)-2-(methoxycarbonyl)-2-(4-methylphenyl)propionic acid 在 草酰氯 作用下， 以 乙醚 、 苯 为溶剂， 反应 12.25h， 生成 (R)-(+)-methyl 4-diazo-2-methyl-2-(4-methylphenyl)-3-oxobutanoate
  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