(1S,2S',4a'S,7'R,8a'R)-1-(3-benzyl-4',4',7'-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2'-yl)-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol | 881748-14-7

• 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: (1S,2S',4a'S,7'R,8a'R)-1-(3-benzyl-4',4',7'-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2'-yl)-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol
• 英文别名: (1S,2'S,4a'S,7'R,8a'R)-1-(3-Benzyl-4',4',7'-trimethyl-octahydro-2H-benzo[e][1,3] oxazin-2'-yl)-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol；(1S)-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]-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol
• CAS: 881748-14-7
• 化学式: C₂₇H₃₄F₃NO₃
• 分子量: 477.567
• InChiKey: SSJXOLHEUBLVLH-FEWHJMLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2S',4a'S,7'R,8a'R)-1-(3-benzyl-4',4',7'-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2'-yl)-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以64%的产率得到(S)-3,3,3-trifluoro-2-hydroxy-2-(4-methoxyphenyl)propanal
  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：

  (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 在 四丁基氟化铵 、 水 、 cesium fluoride 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 10.0h， 生成 (1S,2S',4a'S,7'R,8a'R)-1-(3-benzyl-4',4',7'-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2'-yl)-2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol
  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.