(1'S,5R,6R)-1-hydroxyl-3-(1'-phenylethyl)-5-methoxycarbonyl-6-propylperhydropyrimidin-4-one | 158382-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1'S,5R,6R)-1-hydroxyl-3-(1'-phenylethyl)-5-methoxycarbonyl-6-propylperhydropyrimidin-4-one
• 英文别名: methyl (5R,6R)-1-hydroxy-4-oxo-3-[(1S)-1-phenylethyl]-6-propyl-1,3-diazinane-5-carboxylate
• CAS: 158382-16-2
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: AKJWMPZFAAQMSM-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'S,5R,6R)-1-hydroxyl-3-(1'-phenylethyl)-5-methoxycarbonyl-6-propylperhydropyrimidin-4-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(1'S,2S,3R)-N-(1'-phenylethyl)-2-hydroxymethyl-3-hydroxylaminohexanamide
  参考文献：
  名称：

  Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids

  摘要：

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.

  DOI：

  10.1016/s0040-4020(01)87007-1
• 作为产物：
  描述：

  -N-(1-phenylethyl)-3-O-benzyloxycarbonylhydroxylaminohexanamide 在 对甲苯磺酸 Amberlyst H-15 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.5h， 生成 (1'S,5R,6R)-1-hydroxyl-3-(1'-phenylethyl)-5-methoxycarbonyl-6-propylperhydropyrimidin-4-one
  参考文献：
  名称：

  Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids

  摘要：

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.

  DOI：

  10.1016/s0040-4020(01)87007-1

文献信息

• Synthesis and stereochemical behaviour of 8-alkyl-3-(1-phenylethyl)-7-oxa-1,3-diazabicyclo-[3.2.1]-octane-4,6-diones directed towards the synthesis of α-substituted β-amino acids
  作者：Ilaria Braschi、Giuliana Cardillo、Claudia Tomasini

  DOI：10.1016/s0040-4020(01)87007-1

  日期：1994.2

  A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.