4-oxo-4-[(2S)-2-prop-2-enylpiperidin-1-yl]butanoic acid | 934808-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-oxo-4-[(2S)-2-prop-2-enylpiperidin-1-yl]butanoic acid
• CAS: 934808-02-3
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: FDZMLLLDHKNNOY-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxo-4-[(2S)-2-prop-2-enylpiperidin-1-yl]butanoic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 苯甲酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 41.0h， 生成 9-benzyl-1,3,4,6,7,8,9,10,11,12,13,15,16,17,18,19,20,21,24,24a-eicosahydro-2H,5H-4a,9,13-triaza-benzocyclodocosen-14-one
  参考文献：
  名称：

  Efficient, asymmetric synthesis of (−)-isooncinotine

  摘要：

  Asymmetric synthesis of (-)-isooncinotine, a 22-membered lactam of spermidine alkaloid, starting from resolution of 2-piperidineethanol with (S)-10-camphorsulfonic acid is reported. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when beta-amido- and beta-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed. The synthesis of the skeleton of this macrolide is achieved with ring-closing metathesis of the diene prepared from acylation of the spermidine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.068
• 作为产物：
  描述：

  (2S)-2-prop-2-enylpiperidine;2,2,2-trifluoroacetic acid 、 丁二酸酐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到4-oxo-4-[(2S)-2-prop-2-enylpiperidin-1-yl]butanoic acid
  参考文献：
  名称：

  Efficient, asymmetric synthesis of (−)-isooncinotine

  摘要：

  Asymmetric synthesis of (-)-isooncinotine, a 22-membered lactam of spermidine alkaloid, starting from resolution of 2-piperidineethanol with (S)-10-camphorsulfonic acid is reported. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when beta-amido- and beta-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed. The synthesis of the skeleton of this macrolide is achieved with ring-closing metathesis of the diene prepared from acylation of the spermidine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.068