methyl (9S)-3-(acetyloxy)-9-{formyl[(1R)-1-phenylethyl]amino}-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate | 952489-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl (9S)-3-(acetyloxy)-9-{formyl[(1R)-1-phenylethyl]amino}-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate
• 英文别名: methyl (9S)-3-acetyloxy-9-[formyl-[(1R)-1-phenylethyl]amino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxylate
• CAS: 952489-10-0
• 化学式: C₂₁H₂₃N₃O₆
• 分子量: 413.43
• InChiKey: OGIRCKKOGJQIPB-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (9S)-3-(acetyloxy)-9-{formyl[(1R)-1-phenylethyl]amino}-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到methyl (9S)-3-acetyloxy-9-[methyl-[(1R)-1-phenylethyl]amino]-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxylate
  参考文献：
  名称：

  The synthesis of tetrahydropyridopyrimidones as a new scaffold for HIV-1 integrase inhibitors

  摘要：

  An efficient synthesis of methyl 9-amino-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate as a late stage intermediate for a new class of HIV-1 integrase inhibitors is described. After construction of the bicyclic core scaffold, a stereoselective introduction of the chiral amino group in the 9-position is achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.043
• 作为产物：
  描述：

  methyl 3-(benzoyloxy)-9-bromo-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate 在 4-二甲氨基吡啶 、 TEA 、 乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl (9S)-3-(acetyloxy)-9-{formyl[(1R)-1-phenylethyl]amino}-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate
  参考文献：
  名称：

  The synthesis of tetrahydropyridopyrimidones as a new scaffold for HIV-1 integrase inhibitors

  摘要：

  An efficient synthesis of methyl 9-amino-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate as a late stage intermediate for a new class of HIV-1 integrase inhibitors is described. After construction of the bicyclic core scaffold, a stereoselective introduction of the chiral amino group in the 9-position is achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.043