(+/-)-methyl 3-(1-adamantyl)-3-hydroxypropanoate | 444023-09-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (+/-)-methyl 3-(1-adamantyl)-3-hydroxypropanoate
• 英文别名: Methyl 3-(1-adamantyl)-3-hydroxypropanoate
• CAS: 444023-09-0
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: FEUJIFSUBPNOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 3-(1-adamantyl)-3-hydroxypropanoate 在 palladium on activated charcoal 四氯化碳 、 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 0.5h， 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
• 作为产物：
  描述：

  N-(1-adamantylcarbonyl)imidazole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 (+/-)-methyl 3-(1-adamantyl)-3-hydroxypropanoate
  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.