(3S,4S)-3-methyl-1-(4-methoxyphenyl)-4-(4'-pentynyl)-azetidin-2-one | 192656-47-6

• 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: (3S,4S)-3-methyl-1-(4-methoxyphenyl)-4-(4'-pentynyl)-azetidin-2-one
• 英文别名: (3S,4S)-1-(4-methoxyphenyl)-3-methyl-4-pent-4-ynylazetidin-2-one
• CAS: 192656-47-6
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: IHJQDJLKXOYYDW-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-methyl-1-(4-methoxyphenyl)-4-(4'-pentynyl)-azetidin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.42h， 以86%的产率得到(3S,4S)-3-methyl-4-(4'-pentynyl)-azetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of the β-amino acid methyl ester derivative of onchidin: (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer

  摘要：

  The asymmetric synthesis of the methyl ester of the natural beta-amino acid of Onchidin (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer is described. The preparation of an enantiomerically pure beta-hydroxy acid through an enantioselective aldol condensation reaction and an intramolecular nucleophilic displacement to form a beta-lactam intermediate are the key steps. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00172-9
• 作为产物：
  描述：

  3-hydroxy-2-methyl-7-octynoic acid 在 2,2'-二硫二吡啶 、 potassium tert-butylate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (3S,4S)-3-methyl-1-(4-methoxyphenyl)-4-(4'-pentynyl)-azetidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of the β-amino acid methyl ester derivative of onchidin: (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer

  摘要：

  The asymmetric synthesis of the methyl ester of the natural beta-amino acid of Onchidin (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer is described. The preparation of an enantiomerically pure beta-hydroxy acid through an enantioselective aldol condensation reaction and an intramolecular nucleophilic displacement to form a beta-lactam intermediate are the key steps. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00172-9

文献信息

• Asymmetric synthesis of the β-amino acid methyl ester derivative of onchidin: (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer
  作者：Miryam Fernández-Suárez、Luis Muñoz、Rogelio Fernández、Ricardo Riguera

  DOI：10.1016/s0957-4166(97)00172-9

  日期：1997.6

  The asymmetric synthesis of the methyl ester of the natural beta-amino acid of Onchidin (2S,3S)-methyl-3-amino-2-methyl-7-octynoate and its enantiomer is described. The preparation of an enantiomerically pure beta-hydroxy acid through an enantioselective aldol condensation reaction and an intramolecular nucleophilic displacement to form a beta-lactam intermediate are the key steps. (C) 1997 Elsevier Science Ltd.