3-((R)-1-Hydroxy-4-oxo-azetidin-2-yl)-propionic acid tert-butyl ester | 1026968-65-9

• 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: 3-((R)-1-Hydroxy-4-oxo-azetidin-2-yl)-propionic acid tert-butyl ester
• 英文别名: tert-butyl 3-[(2R)-1-hydroxy-4-oxoazetidin-2-yl]propanoate
• CAS: 1026968-65-9
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: SIUGTXBTHVFUDU-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((R)-1-Hydroxy-4-oxo-azetidin-2-yl)-propionic acid tert-butyl ester 在 对甲苯磺酰叠氮 、 叠氮基三甲基硅烷 、 caesium carbonate 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 4.25h， 生成 (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
• 作为产物：
  描述：

  单叔丁基琥珀酸酯 在 S-Ru-BINAP 四氯化碳 、 氢氧化钾 、 氢气 、 sodium carbonate 、 氯化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 65.0 ℃ 、344.73 kPa 条件下， 反应 44.33h， 生成 3-((R)-1-Hydroxy-4-oxo-azetidin-2-yl)-propionic acid tert-butyl 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).