(R)-3-phenethyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one | 1009605-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: (R)-3-phenethyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-3-phenyl-5-(2-phenylethyl)-2,3-dihydro-1,4-oxazin-6-one
• CAS: 1009605-73-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: FVPLVKOUBIVUGP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-phenethyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one 在 platinum(IV) oxide 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到(3S,5R)-3-phenethyl-5-phenylmorpholin-2-one
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n
• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 、 D-苯甘氨醇 在 3 A molecular sieve 作用下， 以 various solvent(s) 为溶剂， 反应 0.75h， 以54%的产率得到(R)-3-phenethyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n

文献信息

• An Efficient Entry to Optically Active <i>anti</i>- and <i>syn</i>-β-Amino-α-trifluoromethyl Alcohols
  作者：Santos Fustero、Laia Albert、José Luis Aceña、Juan F. Sanz-Cervera、Amparo Asensio

  DOI：10.1021/ol702947n

  日期：2008.2.1

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.