(R)-2-Azetidinepropanoic acid 1-<<(4-methylphenyl)sulfonyl>oxy>-4-oxo-2-(1,1-dimethylethyl) ester | 157435-84-2

• 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: (R)-2-Azetidinepropanoic acid 1-<<(4-methylphenyl)sulfonyl>oxy>-4-oxo-2-(1,1-dimethylethyl) ester
• 英文别名: tert-butyl 3-[(2R)-1-(4-methylphenyl)sulfonyloxy-4-oxoazetidin-2-yl]propanoate
• CAS: 157435-84-2
• 化学式: C₁₇H₂₃NO₆S
• 分子量: 369.439
• InChiKey: ZHQBISWRNYHXAJ-CYBMUJFWSA-N

物化性质

• 沸点：
  466.3±47.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-Azetidinepropanoic acid 1-<<(4-methylphenyl)sulfonyl>oxy>-4-oxo-2-(1,1-dimethylethyl) ester 在 叠氮基三甲基硅烷 、 caesium carbonate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 52.25h， 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 、 二氯甲烷 、 乙腈 为溶剂， 65.0 ℃ 、344.73 kPa 条件下， 反应 44.83h， 生成 (R)-2-Azetidinepropanoic acid 1-<<(4-methylphenyl)sulfonyl>oxy>-4-oxo-2-(1,1-dimethylethyl) 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

• Syntheses of novel bicyclic β-lactams by intramolecular nucleophile transfer reactions of N-tosyloxy β-lactams
  作者：Peter R. Guzzo、Teng Min、Marvin J. Miller

  DOI：10.1016/s0040-4020(01)85552-6

  日期：——

  Intramolecular nucleophile transfer reaction of several N-tosyloxy β-lactams was applied to construct a new six-membered ring in the product bicy

  几种N-甲苯磺酰氧基β-内酰胺的分子内亲核试剂转移反应被用于在产物bicy中构建新的六元环
• 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).