(+/-)-4-(1-adamantyl)-1-tosyloxy-2-azetidinone | 444023-25-0

• 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: (+/-)-4-(1-adamantyl)-1-tosyloxy-2-azetidinone
• 英文别名: [2-(1-Adamantyl)-4-oxoazetidin-1-yl] 4-methylbenzenesulfonate
• CAS: 444023-25-0
• 化学式: C₂₀H₂₅NO₄S
• 分子量: 375.489
• InChiKey: JGGJXDAFQAZGED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(1-adamantyl)-1-tosyloxy-2-azetidinone 在 叠氮基三甲基硅烷 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (+/-)-trans-4-(1-adamantyl)-3-azido-1-benzyl-2-azetidinone
  参考文献：
  名称：

  Enantioselective Synthesis of α-Amino Acids from N-Tosyloxy β-Lactams Derived from β-Keto Esters

  摘要：

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.

  DOI：

  10.1021/jo0162437
• 作为产物：
  描述：

  1-金刚烷甲酸 在 palladium on activated charcoal 四氯化碳 、 sodium tetrahydroborate 、 氢气 、 三甲基铝 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 96.5h， 生成 (+/-)-4-(1-adamantyl)-1-tosyloxy-2-azetidinone
  参考文献：
  名称：

  Enantioselective Synthesis of α-Amino Acids from N-Tosyloxy β-Lactams Derived from β-Keto Esters

  摘要：

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.

  DOI：

  10.1021/jo0162437

文献信息

• Enantioselective Synthesis of α-Amino Acids from <i>N</i>-Tosyloxy β-Lactams Derived from β-Keto Esters
  作者：Timothy B. Durham、Marvin J. Miller

  DOI：10.1021/jo0162437

  日期：2003.1.1

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.