(5S,6R)-3-(2-benzyloxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-2H-1,3,4-oxadiazin-2-one | 612817-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6R)-3-(2-benzyloxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-2H-1,3,4-oxadiazin-2-one
• 英文别名: (5S,6R)-4,5-dimethyl-6-phenyl-3-(2-phenylmethoxyacetyl)-1,3,4-oxadiazinan-2-one
• CAS: 612817-43-3
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: HIUJRJDDVBJGDO-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (5S,6R)-3-(2-benzyloxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-2H-1,3,4-oxadiazin-2-one 在 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (5S,6R)-3-((2S,3R)-2-Benzyloxy-3-hydroxy-3-phenyl-propionyl)-4,5-dimethyl-6-phenyl-[1,3,4]oxadiazinan-2-one
  参考文献：
  名称：

  Oxadiazinones as chiral auxiliaries: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones

  摘要：

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.015
• 作为产物：
  描述：

  (5S,6R)-3-(2-methoxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-6-phenyl-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 (5S,6R)-3-(2-benzyloxyacetyl)-4,5-dimethyl-3,4,5,6-tetrahydro-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: increased diastereoselectivities in the glycolate aldol reaction of oxadiazinones
  作者：Jeremy F. Vaughn、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2004.09.015

  日期：2004.11

  Glycolate aldol reactions were conducted using a (1R,2S)-norephedrine based N-4-isopropyloxadiazinone as a chiral template to afford aldol adducts 8a-h. The yields ranged from 57% to 99% while the diastereoselectivities ranged from 94:6 to 99:1. Adduct 8a was hydrolyzed to afford the oxadiazinone auxiliary and P-hydroxyacid 9, which was converted to the known methyl (2S,3R)-2,3-dihydroxy-3-phenylpropionate 12 with 95% ee as determined by chiral HPLC. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.