(2S,4aS,7R,8aR)-1-(3-benzyl-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl)pentan-1-one | 881748-07-8

• 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: (2S,4aS,7R,8aR)-1-(3-benzyl-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl)pentan-1-one
• 英文别名: 1-[(2S,4aS,7R,8aR)-3-benzyl-4,4,7-trimethyl-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-2-yl]pentan-1-one
• CAS: 881748-07-8
• 化学式: C₂₃H₃₅NO₂
• 分子量: 357.536
• InChiKey: CWVCSUDHTDBKRU-IYERYRBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4aS,7R,8aR)-1-(3-benzyl-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl)pentan-1-one 在 三氯化铝 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-N-benzyl-N-(2-trifluoromethyl-2-hydroxyhexan-1-yl)-8'-aminomenthol
  参考文献：
  名称：

  An Efficient Synthesis of Enantiomerically Enriched Trifluoromethylated 1,2-Diols and 1,2-Amino Alcohols with Quaternary Stereocenters by Diastereoselective Addition of TMSCF₃ to Chiral 2-Acyl-1,3-perhydrobenzoxazines

  摘要：

  TMSCF3 adds to chiral 2-acyl-1,3-perhydrobenzoxazines with total diastereoselectivity leading to quaternary trifluoromethyl alcohols. Further transformation of the addition products yields enantiomerically enriched trifluoromethylated 1,2-diols and 1,2-amino alcohols.

  DOI：

  10.1021/jo052458v
• 作为产物：
  描述：

  (2S,4aS,7R,8aR)-N-benzyl-2-(N-methyl-N-methoxyaminocarbonyl)-4,4,7-trimethyloctahydrobenzo[e][1,3]oxazine 、 正丁基锂 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以96%的产率得到(2S,4aS,7R,8aR)-1-(3-benzyl-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl)pentan-1-one
  参考文献：
  名称：

  An Efficient Synthesis of Enantiomerically Enriched Trifluoromethylated 1,2-Diols and 1,2-Amino Alcohols with Quaternary Stereocenters by Diastereoselective Addition of TMSCF₃ to Chiral 2-Acyl-1,3-perhydrobenzoxazines

  摘要：

  TMSCF3 adds to chiral 2-acyl-1,3-perhydrobenzoxazines with total diastereoselectivity leading to quaternary trifluoromethyl alcohols. Further transformation of the addition products yields enantiomerically enriched trifluoromethylated 1,2-diols and 1,2-amino alcohols.

  DOI：

  10.1021/jo052458v

文献信息

• An Efficient Synthesis of Enantiomerically Enriched Trifluoromethylated 1,2-Diols and 1,2-Amino Alcohols with Quaternary Stereocenters by Diastereoselective Addition of TMSCF₃ to Chiral 2-Acyl-1,3-perhydrobenzoxazines
  作者：Rafael Pedrosa、Sonia Sayalero、Martina Vicente、Alicia Maestro

  DOI：10.1021/jo052458v

  日期：2006.3.1

  TMSCF3 adds to chiral 2-acyl-1,3-perhydrobenzoxazines with total diastereoselectivity leading to quaternary trifluoromethyl alcohols. Further transformation of the addition products yields enantiomerically enriched trifluoromethylated 1,2-diols and 1,2-amino alcohols.