(3S,4R)-1-(4-methoxyphenyl)-3-[3-(4-methoxyphenoxy)prop-1-yl]-4-carbomethoxyazetidin-2-one | 516479-77-9

• 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: (3S,4R)-1-(4-methoxyphenyl)-3-[3-(4-methoxyphenoxy)prop-1-yl]-4-carbomethoxyazetidin-2-one
• 英文别名: methyl (2R,3S)-3-[3-(4-methoxyphenoxy)propyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate
• CAS: 516479-77-9
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: OLJDCMBLSDUNJJ-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-(4-methoxyphenyl)-3-[3-(4-methoxyphenoxy)prop-1-yl]-4-carbomethoxyazetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.75h， 以66%的产率得到(3S,4R)-3-hydroxyprop-1-yl-4-carbomethoxyazetidin-2-one
  参考文献：
  名称：

  Efficient Synthesis of an Enantiopure β-Lactam as an Advanced Precursor of Thrombin and Tryptase Inhibitors

  摘要：

  A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.

  DOI：

  10.1021/jo020617u
• 作为产物：
  描述：

  5-(4-甲氧基苯氧基)戊酸 在 potassium permanganate 、 sodium periodate 、 TEA 、 四氯化钛 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 38.08h， 生成 (3S,4R)-1-(4-methoxyphenyl)-3-[3-(4-methoxyphenoxy)prop-1-yl]-4-carbomethoxyazetidin-2-one
  参考文献：
  名称：

  Efficient Synthesis of an Enantiopure β-Lactam as an Advanced Precursor of Thrombin and Tryptase Inhibitors

  摘要：

  A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.

  DOI：

  10.1021/jo020617u

文献信息

• Efficient Synthesis of an Enantiopure β-Lactam as an Advanced Precursor of Thrombin and Tryptase Inhibitors
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Francesco Maggioni、Alessandra Puglisi

  DOI：10.1021/jo020617u

  日期：2003.4.1

  A new and efficient synthesis of a beta-lactam that is an advanced precursor of inhibitors of thrombin and tryptase is reported. The reaction sequence is based on the use of an inexpensive enantiomerically pure starting material and is designed to allow access to both enantiomers of the target molecules by epimerization of a side-product obtained along the synthesis. An improved procedure for the epimerization step that takes advantage of the use of a polymer-supported and recyclable phase-transfer catalyst is described.