(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester | 157435-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester
• 英文别名: phenyl 3-[(2R,3R)-3-azido-4-oxo-1-(2-oxo-2-phenylmethoxyethyl)azetidin-2-yl]propanoate
• CAS: 157435-88-6
• 化学式: C₂₁H₂₀N₄O₅
• 分子量: 408.414
• InChiKey: VMCRCUNLKGKYSV-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester 在 三乙胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (6R,7R)-1-Azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-8-oxo-7-azidophenylmethyl ester
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of the Carbacephem Framework

  摘要：

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).

  DOI：

  10.1021/jo00096a031
• 作为产物：
  描述：

  在 四氯化碳 、 对甲苯磺酰叠氮 、 叠氮基三甲基硅烷 、 sodium carbonate 、 caesium carbonate 、 苯甲醚 、 三乙胺 、 氯甲酸苯酯 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.66h， 生成 (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azidophenyl ester
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of the Carbacephem Framework

  摘要：

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).

  DOI：

  10.1021/jo00096a031

文献信息

• Catalytic, Asymmetric Synthesis of the Carbacephem Framework
  作者：Peter R. Guzzo、Marvin J. Miller

  DOI：10.1021/jo00096a031

  日期：1994.8

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).