E-2-<4-O-benzoyl-(3S)-3-hydroxy-1-butenyl>-3-methylquinoxaline | 154344-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: E-2-<4-O-benzoyl-(3S)-3-hydroxy-1-butenyl>-3-methylquinoxaline
• CAS: 154344-73-7
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: HUIIITPDKPNMDI-PCUGXKRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.31
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  E-2-<4-O-benzoyl-(3S)-3-hydroxy-1-butenyl>-3-methylquinoxaline 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 2-<4-O-benzoyl-(3S)-3-hydroxybutyl>-3-methylquinoxaline
  参考文献：
  名称：

  C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside

  摘要：

  The synthesis of quinoxaline acyclo-C-nucleoside, 2-[(3S)-3,4-dihydroxybutyl]3-methylquinoxaline (6), is described. Treatment of furanone glycoside (1) with 1,2-diaminobenze gave a mixture of Z- and E-3-[2-[4-0-benzoyl-(3S)-3-hydroxy-1-butenyl]-3-quinoxalinylmethyl]-1,2,3,4-tetrahydroquinoxalin-2-ones (2a and 2b). Compound (2a) was treated with acetic acid to give three products, Z- and E-(3S)-3-hydroxy-1-butenyl]-3-methylquinoxalines (3a and 3b) and quinoxalin-2-one (4). Catalytic hydrogenation of 3a,b produced 2-[4-0-benzoyl-(3S)-3-hydroxybutyl]-3-methylquinoxaline (5). Removal of the protecting group in 5 afforded compound (6).

  DOI：

  10.3987/com-93-6501
• 作为产物：
  描述：

  Z-3-<2-<4-O-benzoyl-(3S)-3-hydroxy-1-butenyl>-3-quinoxalinylmethyl>-1,2,3,4-tetrahydroquinoxalin-2-one 在 溶剂黄146 作用下， 反应 2.0h， 以34%的产率得到E-2-<4-O-benzoyl-(3S)-3-hydroxy-1-butenyl>-3-methylquinoxaline
  参考文献：
  名称：

  C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside

  摘要：

  The synthesis of quinoxaline acyclo-C-nucleoside, 2-[(3S)-3,4-dihydroxybutyl]3-methylquinoxaline (6), is described. Treatment of furanone glycoside (1) with 1,2-diaminobenze gave a mixture of Z- and E-3-[2-[4-0-benzoyl-(3S)-3-hydroxy-1-butenyl]-3-quinoxalinylmethyl]-1,2,3,4-tetrahydroquinoxalin-2-ones (2a and 2b). Compound (2a) was treated with acetic acid to give three products, Z- and E-(3S)-3-hydroxy-1-butenyl]-3-methylquinoxalines (3a and 3b) and quinoxalin-2-one (4). Catalytic hydrogenation of 3a,b produced 2-[4-0-benzoyl-(3S)-3-hydroxybutyl]-3-methylquinoxaline (5). Removal of the protecting group in 5 afforded compound (6).

  DOI：

  10.3987/com-93-6501