(+)-(2S)-Dimethyl 2-methyl-2-((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)pentane-1,5-dioate | 151075-02-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(2S)-Dimethyl 2-methyl-2-((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)pentane-1,5-dioate
• 英文别名: (+)-(2S)-Dimethyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>pentane-1,5-dioate
• CAS: 151075-02-4
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: BUGCOODPICZIQI-DYVFJYSZSA-N

物化性质

• 沸点：
  514.6±50.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+)-(2S)-Dimethyl 2-methyl-2-((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)pentane-1,5-dioate 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以93%的产率得到2-methyl-2-((S)-2-oxo-4-phenyloxazolidin-3-yl)pentanedioic acid
  参考文献：
  名称：

  Asymmetric synthesis of .alpha.-alkyl-.alpha. amino acids from chromium-carbene-complex-derived .beta.-lactams

  摘要：

  Optically active bicyclic beta-lactam 3 was synthesized by photolysis of optically active oxazolidine carbene chromium complex 1 with oxazine 2. Conversion of the oxazolidine to the oxazolidinone gave a bicyclic beta-lactam readily alpha-alkylated. Cleavage of the alkylated beta-lactam gave optically active ester aldehyde 7, which was converted to a number of optically active alpha-alkyl-alpha-amino acids. These include (R)-alpha-methylserine, (S)-alpha-methylglutamic acid, (S)-alpha-methylornithine, (S)-vinylalanine, (S)-ethynylalanine, and (S)-2-methyl-2,3-diaminopropionic acid.

  DOI：

  10.1021/jo00074a016
• 作为产物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 136.0h， 生成 (+)-(2S)-Dimethyl 2-methyl-2-((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)pentane-1,5-dioate
  参考文献：
  名称：

  Asymmetric synthesis of .alpha.-alkyl-.alpha. amino acids from chromium-carbene-complex-derived .beta.-lactams

  摘要：

  Optically active bicyclic beta-lactam 3 was synthesized by photolysis of optically active oxazolidine carbene chromium complex 1 with oxazine 2. Conversion of the oxazolidine to the oxazolidinone gave a bicyclic beta-lactam readily alpha-alkylated. Cleavage of the alkylated beta-lactam gave optically active ester aldehyde 7, which was converted to a number of optically active alpha-alkyl-alpha-amino acids. These include (R)-alpha-methylserine, (S)-alpha-methylglutamic acid, (S)-alpha-methylornithine, (S)-vinylalanine, (S)-ethynylalanine, and (S)-2-methyl-2,3-diaminopropionic acid.

  DOI：

  10.1021/jo00074a016