trans-(3S,4R)-(-)-3-ethyl-4-hydroxymethylazetidin-2-one | 315696-07-2

• 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: trans-(3S,4R)-(-)-3-ethyl-4-hydroxymethylazetidin-2-one
• 英文别名: (3S,4R)-3-ethyl-4-(hydroxymethyl)azetidin-2-one
• CAS: 315696-07-2
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: OQUFUBGNYKRLBT-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(3S,4R)-(-)-3-ethyl-4-hydroxymethylazetidin-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 calcium carbonate 作用下， 以 苯 为溶剂， 反应 4.0h， 以10 mg的产率得到trans-4-acetoxy-3-ethylazetidin-2-one
  参考文献：
  名称：

  A Novel Approach to a Precursor of the Carbapenem Antibiotic PS-5 via Aziridine Stereospecific Carbonylation

  摘要：

  Cobalt cartonyl-catalyzed carbonylative ring expansion of optically pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans-beta -lactam (8) afforded a key precursor of the carbapenem antibiotic (+)-PS-5. Aziridine (5) was obtained in both enantiomerically pure forms by Amano PS lipase-catalyzed esterification in n-hexane using vinyl acetate as acyl donor. The stereochemical pathway of the carbonylation reaction was proved by configurational assignments through chemical correlation.

  DOI：

  10.3987/com-00-8974
• 作为产物：
  描述：

  反-2-戊酸甲酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 dicobalt octacarbonyl 、 Amano PS Lipase 、 四丁基氟化铵 、 氨 、 溴 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 为溶剂， -42.0~105.0 ℃ 、3.45 MPa 条件下， 反应 18.5h， 生成 trans-(3S,4R)-(-)-3-ethyl-4-hydroxymethylazetidin-2-one
  参考文献：
  名称：

  A Novel Approach to a Precursor of the Carbapenem Antibiotic PS-5 via Aziridine Stereospecific Carbonylation

  摘要：

  Cobalt cartonyl-catalyzed carbonylative ring expansion of optically pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans-beta -lactam (8) afforded a key precursor of the carbapenem antibiotic (+)-PS-5. Aziridine (5) was obtained in both enantiomerically pure forms by Amano PS lipase-catalyzed esterification in n-hexane using vinyl acetate as acyl donor. The stereochemical pathway of the carbonylation reaction was proved by configurational assignments through chemical correlation.

  DOI：

  10.3987/com-00-8974

文献信息

• A Novel Approach to a Precursor of the Carbapenem Antibiotic PS-5 via Aziridine Stereospecific Carbonylation
  作者：Paolo Davoli、Fabio Prati

  DOI：10.3987/com-00-8974

  日期：——

  Cobalt cartonyl-catalyzed carbonylative ring expansion of optically pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans-beta -lactam (8) afforded a key precursor of the carbapenem antibiotic (+)-PS-5. Aziridine (5) was obtained in both enantiomerically pure forms by Amano PS lipase-catalyzed esterification in n-hexane using vinyl acetate as acyl donor. The stereochemical pathway of the carbonylation reaction was proved by configurational assignments through chemical correlation.