(+)-(6S,7S)-7-Methyl-7-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one | 151124-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(6S,7S)-7-Methyl-7-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one
• 英文别名: (6S,7S)-7-methyl-7-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-oxa-1-azabicyclo[4.2.0]octan-8-one
• CAS: 151124-11-7
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: JMKRAWZVSDIYMD-IVMMDQJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(6S,7S)-7-Methyl-7-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 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 171.0h， 生成
  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 盐酸 、 双(三甲基硅烷基)氨基钾 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.75h， 生成 (+)-(6S,7S)-7-Methyl-7-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one
  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

文献信息

• Asymmetric synthesis of .alpha.-alkyl-.alpha. amino acids from chromium-carbene-complex-derived .beta.-lactams
  作者：Pierre Jean Colson、Louis S. Hegedus

  DOI：10.1021/jo00074a016

  日期：1993.10

  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.