(S)-5-allyl-3-methylenetetrahydropyran-2-one | 1072956-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-5-allyl-3-methylenetetrahydropyran-2-one
• 英文别名: (5S)-3-methylidene-5-prop-2-enyloxan-2-one
• CAS: 1072956-39-8
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: VZPSCLVOPNQLSR-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (5S)-5-allyl-3-diethoxyphosphoryl-2-oxotetrahydro-2H-pyran 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以50%的产率得到(S)-5-allyl-3-methylenetetrahydropyran-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.