(4S,4aR,8aS)-8a-[(N-methyl-S-phenylsulfonimidoyl)methyl]-4-propan-2-yl-4,4a,5,6,7,8-hexahydro-1H-benzo[d][1,3]oxazin-2-one | 283594-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (4S,4aR,8aS)-8a-[(N-methyl-S-phenylsulfonimidoyl)methyl]-4-propan-2-yl-4,4a,5,6,7,8-hexahydro-1H-benzo[d][1,3]oxazin-2-one
• CAS: 283594-60-5
• 化学式: C₁₉H₂₈N₂O₃S
• 分子量: 364.509
• InChiKey: FPUVYTDSNDDCRY-OPHPKWAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,4aR,8aS)-8a-[(N-methyl-S-phenylsulfonimidoyl)methyl]-4-propan-2-yl-4,4a,5,6,7,8-hexahydro-1H-benzo[d][1,3]oxazin-2-one 在 镍 正丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 methyl 2-[(4S,4aR,8aR)-2-oxo-4-propan-2-yl-4,4a,5,6,7,8-hexahydro-1H-benzo[d][1,3]oxazin-8a-yl]acetate
  参考文献：
  名称：

  Diastereoselective amination of vinylic sulfoximines: application to the asymmetric synthesis of functionalized β-substituted and β,β-disubstituted β-amino acids, and of γ-amino alcohols

  摘要：

  An asymmetric synthesis of protected beta-substituted and beta,beta-disubstituted beta-amino acids, which carry a hydroxyalkyl side chain, from sulfonimidoyl functionalized homoallylic alcohols is described. The method allows for an asymmetric synthesis of amino alcohols as well. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00307-5
• 作为产物：
  描述：

  (-)-(Z)-(S)-1-{(R)-2-[(S)-N-methyl-S-phenylsulfonimidoyl]methylenecyclohexyl}-2-methylpropan-1-ol 在 ammonium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (4S,4aR,8aS)-8a-[(N-methyl-S-phenylsulfonimidoyl)methyl]-4-propan-2-yl-4,4a,5,6,7,8-hexahydro-1H-benzo[d][1,3]oxazin-2-one
  参考文献：
  名称：

  Diastereoselective amination of vinylic sulfoximines: application to the asymmetric synthesis of functionalized β-substituted and β,β-disubstituted β-amino acids, and of γ-amino alcohols

  摘要：

  An asymmetric synthesis of protected beta-substituted and beta,beta-disubstituted beta-amino acids, which carry a hydroxyalkyl side chain, from sulfonimidoyl functionalized homoallylic alcohols is described. The method allows for an asymmetric synthesis of amino alcohols as well. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00307-5

文献信息

• Diastereoselective amination of vinylic sulfoximines: application to the asymmetric synthesis of functionalized β-substituted and β,β-disubstituted β-amino acids, and of γ-amino alcohols
  作者：Hans-Joachim Gais、Ralf Loo、Parthasarathi Das、Gerhard Raabe

  DOI：10.1016/s0040-4039(00)00307-5

  日期：2000.4

  An asymmetric synthesis of protected beta-substituted and beta,beta-disubstituted beta-amino acids, which carry a hydroxyalkyl side chain, from sulfonimidoyl functionalized homoallylic alcohols is described. The method allows for an asymmetric synthesis of amino alcohols as well. (C) 2000 Elsevier Science Ltd. All rights reserved.