3-benzyl-4-cyclohexyl-oxazolidine-2,5-dione | 444023-49-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-benzyl-4-cyclohexyl-oxazolidine-2,5-dione
• 英文别名: 3-Benzyl-4-cyclohexyl-1,3-oxazolidine-2,5-dione
• CAS: 444023-49-8
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: CTECKGZCPIVWPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-benzyl-4-cyclohexyl-oxazolidine-2,5-dione 在 三甲基氯硅烷 作用下， 反应 0.25h， 以4 mg的产率得到methyl 2-(N-benzylamino)-2-cyclohexylethanoate hydrochloride
  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：

  3-环己基-3-氧代丙酸甲酯 在 palladium on activated charcoal 四氯化碳 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium tetrahydroborate 、 对甲苯磺酰叠氮 、 次氯酸叔丁酯 、 叠氮基三甲基硅烷 、 氢气 、 三甲基铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 cesium fluoride 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 109.43h， 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