4-(2-allyl-piperidin-1-yl)-N-benzyl-4-oxo-butyramide | 934808-09-0

• 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-(2-allyl-piperidin-1-yl)-N-benzyl-4-oxo-butyramide
• CAS: 934808-09-0
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: MFLQPSWTHDUCGA-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2-allyl-piperidin-1-yl)-N-benzyl-4-oxo-butyramide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成
  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：

  4-oxo-4-[(2S)-2-prop-2-enylpiperidin-1-yl]butanoic acid 、 苄胺 在 4-二甲氨基吡啶 、 苯甲酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以10%的产率得到4-(2-allyl-piperidin-1-yl)-N-benzyl-4-oxo-butyramide
  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