(+/-)-trans-3-azido-4-cyclohexyl-2-azetidinone

• 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-3-azido-4-cyclohexyl-2-azetidinone
• 英文别名: (3R,4R)-3-azido-4-cyclohexylazetidin-2-one
• 化学式: C₉H₁₄N₄O
• 分子量: 194.236
• InChiKey: AYBBHVYVBSYBPP-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-3-azido-4-cyclohexyl-2-azetidinone 在 10percent Pd/C 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 次氯酸叔丁酯 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cesium fluoride 、 potassium bromide 作用下， 以 四氢呋喃 、 phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.43h， 生成 3-benzyl-4-cyclohexyl-oxazolidine-2,5-dione
  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：

  (+/-)-methyl 3-(cyclohexyl)-3-hydroxypropanoate 在 palladium on activated charcoal 四氯化碳 、 对甲苯磺酰叠氮 、 叠氮基三甲基硅烷 、 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 甲醇 、 正庚烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 108.0h， 生成 (+/-)-trans-3-azido-4-cyclohexyl-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

• An Enantioselective Synthesis of Differentially Protected <i>erythro</i>-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5
  作者：Timothy B. Durham、Marvin J. Miller

  DOI：10.1021/jo016276m

  日期：2003.1.1

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.