(5S)-1-benzyl-3-diethoxyphosphoryl-5-isopropylpiperidin-2-one | 1072956-42-3

• 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: (5S)-1-benzyl-3-diethoxyphosphoryl-5-isopropylpiperidin-2-one
• 英文别名: (5S)-1-benzyl-3-diethoxyphosphoryl-5-propan-2-ylpiperidin-2-one
• CAS: 1072956-42-3
• 化学式: C₁₉H₃₀NO₄P
• 分子量: 367.425
• InChiKey: FIMHOEZPGYSBFK-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (5S)-1-benzyl-3-diethoxyphosphoryl-5-isopropylpiperidin-2-one 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 0.75h， 生成 (S)-1-benzyl-5-isopropyl-3-methylenepiperidin-2-one 、 (R)-1-benzyl-5-isopropyl-3-methylenepiperidin-2-one
  参考文献：
  名称：

  Enantioselective Organocatalytic Approach to α-Methylene-δ-lactones and δ-Lactams

  摘要：

  We present the first enantioselective organocatalytic approach for the synthesis of alpha-methylene-delta-lactones and delta-lactams. Our methodology utilizes the Michael addition of Unmodified aldehydes to ethyl 2-(diethoxyphosphoryl)acrylate as the key step affording highly enantiomerically enriched adducts, which can be transformed into the target Compounds maintaining the high stereoselectivity achieved in the first step. This methodology has been shown to be general and various optically active gamma-substituted alpha-methylene-delta-lactones and delta-lactams can be easily accessed.

  DOI：

  10.1021/jo801582t
• 作为产物：
  描述：

  ethyl (4S)-2-diethoxyphosphoryl-4-formyl-5-methylhexanoate 、 苄胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 (5S)-1-benzyl-3-diethoxyphosphoryl-5-isopropylpiperidin-2-one
  参考文献：
  名称：

  Enantioselective Organocatalytic Approach to α-Methylene-δ-lactones and δ-Lactams

  摘要：

  We present the first enantioselective organocatalytic approach for the synthesis of alpha-methylene-delta-lactones and delta-lactams. Our methodology utilizes the Michael addition of Unmodified aldehydes to ethyl 2-(diethoxyphosphoryl)acrylate as the key step affording highly enantiomerically enriched adducts, which can be transformed into the target Compounds maintaining the high stereoselectivity achieved in the first step. This methodology has been shown to be general and various optically active gamma-substituted alpha-methylene-delta-lactones and delta-lactams can be easily accessed.

  DOI：

  10.1021/jo801582t

文献信息

• Enantioselective Organocatalytic Approach to α-Methylene-δ-lactones and δ-Lactams
  作者：Łukasz Albrecht、Bo Richter、Henryk Krawczyk、Karl Anker Jørgensen

  DOI：10.1021/jo801582t

  日期：2008.11.7

  We present the first enantioselective organocatalytic approach for the synthesis of alpha-methylene-delta-lactones and delta-lactams. Our methodology utilizes the Michael addition of Unmodified aldehydes to ethyl 2-(diethoxyphosphoryl)acrylate as the key step affording highly enantiomerically enriched adducts, which can be transformed into the target Compounds maintaining the high stereoselectivity achieved in the first step. This methodology has been shown to be general and various optically active gamma-substituted alpha-methylene-delta-lactones and delta-lactams can be easily accessed.