(-)-(4S,6S)-6-methyl-4-vinyl-1,3-oxazinan-2-one | 1185061-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (-)-(4S,6S)-6-methyl-4-vinyl-1,3-oxazinan-2-one
• 英文别名: (4S,6S)-4-ethenyl-6-methyl-1,3-oxazinan-2-one
• CAS: 1185061-32-8
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: BJEYEEIRHKNLDO-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(4S,6S)-6-methyl-4-vinyl-1,3-oxazinan-2-one 、 but-3-en-1-yl triflate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以89%的产率得到(-)-(4S,6S)-3-(but-3-enyl)-6-methyl-4-vinyl-1,3-oxazinan-2-one
  参考文献：
  名称：

  Allylic C−H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

  摘要：

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

  DOI：

  10.1021/ja9054959
• 作为产物：
  描述：

  (+)-(4S,6S)-6-methyl-3-(4-nitrophenylsulfonyl)-4-vinyl-1,3-oxazinan-2-one 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到(-)-(4S,6S)-6-methyl-4-vinyl-1,3-oxazinan-2-one
  参考文献：
  名称：

  Allylic C−H Amination for the Preparation of syn-1,3-Amino Alcohol Motifs

  摘要：

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.

  DOI：

  10.1021/ja9054959

文献信息

• Allylic C−H Amination for the Preparation of <i>syn</i>-1,3-Amino Alcohol Motifs
  作者：Grant T. Rice、M. Christina White

  DOI：10.1021/ja9054959

  日期：2009.8.26

  A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.