(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-phenylethanol | 881748-12-5

• 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: (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-phenylethanol
• 英文别名: (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-phenylethanol
• CAS: 881748-12-5
• 化学式: C₂₆H₃₂F₃NO₂
• 分子量: 447.541
• InChiKey: JYQFUSVPYZNBIU-LOAAWLJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  6

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-phenylethanol 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 (S)-3,3,3-trifluoro-2-phenylpropane-1,2-diol
  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)-2-benzoyl-N-benzyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 在 四丁基氟化铵 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 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-phenylethanol
  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.