(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azide | 157435-87-5

• 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-azide
• 英文别名: 3-[(2R,3R)-3-azido-4-oxo-1-(2-oxo-2-phenylmethoxyethyl)azetidin-2-yl]propanoic acid
• CAS: 157435-87-5
• 化学式: C₁₅H₁₆N₄O₅
• 分子量: 332.316
• InChiKey: XYYZIWHEGXHHQK-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 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-azide 在 三乙胺 、 氯甲酸苯酯 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 生成 (6R,7R)-7-Azido-3,8-dioxo-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl 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：

  (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azido-(1,1-dimethylethyl) ester 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.25h， 以82%的产率得到(2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azide
  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).