ethyl methyl (S)-2-acetyl-2-methylsuccinate | 89656-87-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl methyl (S)-2-acetyl-2-methylsuccinate
• 英文别名: 1-O-ethyl 4-O-methyl (2S)-2-acetyl-2-methylbutanedioate
• CAS: 89656-87-1
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: HMXCJZSHSVHNHZ-JTQLQIEISA-N

物化性质

• 沸点：
  288.8±20.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 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：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl methyl (S)-2-acetyl-2-methylsuccinate 生成 L-α-methylaspartic acid 、 (R)-(-)-2-氨基-2-甲基丁二酸
  参考文献：
  名称：

  通过α，α-双烷基化的β-酮酯的Schmidt重排不对称合成α-烷基化的α-氨基酸

  摘要：

  通过光学活性α，α-双烷基化β-酮酯的施密特重排，可以高收率和光学纯度获得α-烷基化的α-氨基酸。

  DOI：

  10.1016/s0040-4039(00)80107-0
• 作为产物：
  描述：

  N-[2-(ethoxycarbonyl)-1-methylprop-1-enyl]-L-valine tert-butyl ester 生成 ethyl methyl (S)-2-acetyl-2-methylsuccinate
  参考文献：
  名称：

  Stereoselective reactions. XXI. Asymmetric alkylation of α-alkyl β-keto esters to α,α-dialkyl β-keto esters having either (R)- or (S)-chiral quaternary center depending on the solvent system

  摘要：

  Asymmetric alkylation reaction of chiral enamines prepared from alpha-alkyl beta-keto esters and (S)-valine tert-butyl ester leading to either enantiomer is described. Lithiated chiral enamines can be alkylated with alkyl halides in a toluene solvent in the presence of HMPA to give, after hydrolysis, alpha,alpha-dialkyl beta-keto esters in 70-99%ee. The reactions in the presence of THF, dioxolane, or trimethylamine. instead of HMPA, afford the corresponding antipodes with enantiomeric purities of 44-92%ee. The present method provides a procedure for the synthesis of both enantiomers of alpha,alpha-dialkyl beta-keto esters in high enantiomeric purities starting from the same chiral enamines.

  DOI：

  10.1016/s0040-4020(01)80346-x

文献信息

• TOMIOKA, KIYOSHI;ANDO, KAORI;TAKEMASA, YUTAKA;KOGA, KENJI, J. AMER. CHEM. SOC., 1984, 106, N 9, 2718-2719
  作者：TOMIOKA, KIYOSHI、ANDO, KAORI、TAKEMASA, YUTAKA、KOGA, KENJI

  DOI：——

  日期：——
• GEORG, GUNDA I.;GUAN, XIANGMING;KANT, JOYDEEP, TETRAHEDRON LETT., 29,(1988) N 4, 403-406
  作者：GEORG, GUNDA I.、GUAN, XIANGMING、KANT, JOYDEEP

  DOI：——

  日期：——
• Stereoselective reactions. XXI. Asymmetric alkylation of α-alkyl β-keto esters to α,α-dialkyl β-keto esters having either (R)- or (S)-chiral quaternary center depending on the solvent system
  作者：Kaori Ando、Yataka Takemasa、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4020(01)80346-x

  日期：——

  Asymmetric alkylation reaction of chiral enamines prepared from alpha-alkyl beta-keto esters and (S)-valine tert-butyl ester leading to either enantiomer is described. Lithiated chiral enamines can be alkylated with alkyl halides in a toluene solvent in the presence of HMPA to give, after hydrolysis, alpha,alpha-dialkyl beta-keto esters in 70-99%ee. The reactions in the presence of THF, dioxolane, or trimethylamine. instead of HMPA, afford the corresponding antipodes with enantiomeric purities of 44-92%ee. The present method provides a procedure for the synthesis of both enantiomers of alpha,alpha-dialkyl beta-keto esters in high enantiomeric purities starting from the same chiral enamines.
• Asymmetric synthesis of α-alkylated α-amino acids via Schmidt rearrangement of α, α-bisalkylated β-keto esters
  作者：Gunda I. Georg、Xiangming Guan、Joydeep Kant

  DOI：10.1016/s0040-4039(00)80107-0

  日期：1988.1

  α-Alkylated α-amino acids are obtained in high yield and optical purity through Schmidt rearrangement of optically active α,α-bisalkylated β-keto esters.

  通过光学活性α，α-双烷基化β-酮酯的施密特重排，可以高收率和光学纯度获得α-烷基化的α-氨基酸。