3-O-methoxycarbonyl 1-O-methyl (2S)-2-methyl-2-(4-methylphenyl)propanedioate | 127047-09-0

• 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: 3-O-methoxycarbonyl 1-O-methyl (2S)-2-methyl-2-(4-methylphenyl)propanedioate
• CAS: 127047-09-0
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: FCZLFESHSLVRFR-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-O-methoxycarbonyl 1-O-methyl (2S)-2-methyl-2-(4-methylphenyl)propanedioate 在 咪唑 、 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 sodium acetate 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.92h， 生成 (R)-(+)-4-methyl-2-oxo-4-(4-methylphenyl)-4-butanolide
  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：

  methyl 2-(4-methylphenyl)propanoate 在 sodium hydroxide 、 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 生成 3-O-methoxycarbonyl 1-O-methyl (2S)-2-methyl-2-(4-methylphenyl)propanedioate
  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

• Reverse chemoselective borane reduction of an optically active malonic acid ester
  作者：Antoine Fadel、Jean-Louis Canet、Jacques Salaun

  DOI：10.1016/s0040-4039(00)70651-4

  日期：——

  Reduction of the 2-methyl-2-p-tolylmalonic monoester (+)-2 with the borane-dimethylsulfide complex took place unexpectedly on the ester function,providing the β-hydroxy-acid (−)-3. This chemoselective reaction proceeded likely through formation of a six-membered ring monoacyloxyborane intermediate 6a and intramolecular hydride transfer.

  用硼烷-二甲基硫醚络合物还原2-甲基-2-对甲苯基丙二酸单酯（+）- 2意外地在酯官能团上发生，提供了β-羟基酸（-）- 3。该化学选择性反应很可能通过形成六元环单酰氧基硼烷中间体6a和分子内氢化物转移而进行。
• FADEL, ANTOINE;CANET, JEAN-LOUIS;SALAUN, JACQUES, TETRAHEDRON LETT., 30,(1989) N8, C. 6687-6690
  作者：FADEL, ANTOINE、CANET, JEAN-LOUIS、SALAUN, JACQUES

  DOI：——

  日期：——