(2'S,3'R,5S,6R)-3,4,5,6-tetrahydro-3-[3-hydroxy-2-methoxy-3-(4-methoxyphenyl)propionyl]-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2'S,3'R,5S,6R)-3,4,5,6-tetrahydro-3-[3-hydroxy-2-methoxy-3-(4-methoxyphenyl)propionyl]-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one
• 英文别名: (5S,6R)-3-[(2S,3R)-3-hydroxy-2-methoxy-3-(4-methoxyphenyl)propanoyl]-4,5-dimethyl-6-phenyl-1,3,4-oxadiazinan-2-one
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: ADQUBWBJFJGHON-WBCYEJBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (5S,6R)-4,5-dimethyl-6-phenyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one 在 四氯化钛 、 lithium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.42h， 生成 (2'S,3'R,5S,6R)-3,4,5,6-tetrahydro-3-[3-hydroxy-2-methoxy-3-(4-methoxyphenyl)propionyl]-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazin-2-one
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones

  摘要：

  Asymmetric aldol reactions have been conducted with a series of N-3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine. These reactions afford the non-Evans syn-adducts in 43-97% yield and diastereoselectivities ranging from 62:38 to 99:1. Oxadiazinone substrates substituted with either the phenoxyacetyl or p-methoxyphenoxyacetyl groups gave the best results whereas the methoxyacetyl substituted oxadiazinone afforded diastereoselectivities that were modest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.020

文献信息

• Oxadiazinones as chiral auxiliaries: diastereoselective aldol addition reactions of N3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones
  作者：Trisha R. Hoover、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2003.07.020

  日期：2003.10

  Asymmetric aldol reactions have been conducted with a series of N-3-glycolyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-ephedrine. These reactions afford the non-Evans syn-adducts in 43-97% yield and diastereoselectivities ranging from 62:38 to 99:1. Oxadiazinone substrates substituted with either the phenoxyacetyl or p-methoxyphenoxyacetyl groups gave the best results whereas the methoxyacetyl substituted oxadiazinone afforded diastereoselectivities that were modest. (C) 2003 Elsevier Ltd. All rights reserved.