(6S,7S)-7-<(4S)-2-Oxo-4-phenyl-1,3-oxazolidin-3-yl>-1-aza-5-oxabicyclo<4.2.0>octan-8-one | 134627-50-2

• 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-<(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-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-5-oxa-1-azabicyclo[4.2.0]octan-8-one
• CAS: 134627-50-2
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: FIXZGQRILIUVEO-BZPMIXESSA-N

物化性质

• 沸点：
  587.8±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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-<(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 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~25.0 ℃ 、206.84 kPa 条件下， 反应 209.25h， 生成 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 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (6S,7S)-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

• A contribution to the confusion surrounding the reaction of ketenes with imines to produce .beta.-lactams. A comparison of stereoselectivity dependence on the method of ketene generation: acid chloride/triethylamine vs photolysis of chromium carbene complexes
  作者：Louis S. Hegedus、John Montgomery、Yukitoshi Narukawa、Daniel C. Snustad

  DOI：10.1021/ja00015a036

  日期：1991.7

  The stereoselectivity of the reaction of imines of benzaldehyde and cinnamaldehyde with ketenes generated by the reaction of optically active oxazolidinone acid chlorides with triethylamine and complexed ketenes generated by photolysis of optically active oxazolidine ― and oxazolidinone-chromium-carbene complexes in the presence and absence of added triethylamine was compared. The absolute stereochemistry

  苯甲醛和肉桂醛的亚胺与旋光性恶唑烷酮酰氯与三乙胺反应生成的烯酮和旋光性恶唑烷-和恶唑烷酮-铬-卡宾配合物光解生成的络合烯酮反应的立体选择性三乙胺进行了比较。绝对立体化学主要由手性助剂的结构决定。相对（顺反）立体化学主要由亚胺的结构和乙烯酮的游离或结合特性决定。三乙胺加成到卡宾配合物的反应中得到的结果与酰氯生成的乙烯酮的结果非常相似。
• 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.