4-[N-methyl-N-(2-bromo-5-methoxybenzyl)]amino-6-methylbenzopyran-7-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-[N-methyl-N-(2-bromo-5-methoxybenzyl)]amino-6-methylbenzopyran-7-one
• 英文别名: 4-[(2-Bromo-5-methoxyphenyl)methyl-methylamino]-6-methylchromen-2-one
• 化学式: C₁₉H₁₈BrNO₃
• 分子量: 388.261
• InChiKey: AKBFNCGDNPODIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[N-methyl-N-(2-bromo-5-methoxybenzyl)]amino-6-methylbenzopyran-7-one 在 偶氮二异丁腈 、 三丁基氯化锡 、 sodium cyanoborohydride 作用下， 以 苯 为溶剂， 反应 5.0h， 以67%的产率得到8-methoxy-3,5-dimethylchromeno[4,3-c]isoquinolin-11-one
  参考文献：
  名称：

  Regioselective Synthesis of Chromeno[4,3‐c] isoquinolin‐11‐ones by Radical Cyclization

  摘要：

  A number of 4-tosyloxycoumarins were treated with N-methyl,N-(2-bromobenzyl)amine, and N-methyl,N-(2-bromo-5-methoxybenzyl)amine in refluxing ethanol to give different 4-[N-(2'-bromobenzy]),N-methyl] amino coumarins in 70-75% yield. These tertiary amine substrates were then refluxed in dry benzene under nitrogen with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of 0.5-0.6 mol equiv. of azobisisobutyronitrile(AIBN) for 4-5 hr to give the title compounds in 65-68% yield.

  DOI：

  10.1081/scc-200026621
• 作为产物：
  描述：

  N-(2-bromo-5-methoxybenzyl),N-methylamine 、 6-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate 以 乙醇 为溶剂， 反应 10.0h， 以73%的产率得到4-[N-methyl-N-(2-bromo-5-methoxybenzyl)]amino-6-methylbenzopyran-7-one
  参考文献：
  名称：

  Regioselective Synthesis of Chromeno[4,3‐c] isoquinolin‐11‐ones by Radical Cyclization

  摘要：

  A number of 4-tosyloxycoumarins were treated with N-methyl,N-(2-bromobenzyl)amine, and N-methyl,N-(2-bromo-5-methoxybenzyl)amine in refluxing ethanol to give different 4-[N-(2'-bromobenzy]),N-methyl] amino coumarins in 70-75% yield. These tertiary amine substrates were then refluxed in dry benzene under nitrogen with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of 0.5-0.6 mol equiv. of azobisisobutyronitrile(AIBN) for 4-5 hr to give the title compounds in 65-68% yield.

  DOI：

  10.1081/scc-200026621

文献信息

• Regioselective Synthesis of Chromeno[4,3‐<i>c</i>] isoquinolin‐11‐ones by Radical Cyclization
  作者：K. C. Majumdar、S. Sarkar

  DOI：10.1081/scc-200026621

  日期：2004.1.1

  A number of 4-tosyloxycoumarins were treated with N-methyl,N-(2-bromobenzyl)amine, and N-methyl,N-(2-bromo-5-methoxybenzyl)amine in refluxing ethanol to give different 4-[N-(2'-bromobenzy]),N-methyl] amino coumarins in 70-75% yield. These tertiary amine substrates were then refluxed in dry benzene under nitrogen with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of 0.5-0.6 mol equiv. of azobisisobutyronitrile(AIBN) for 4-5 hr to give the title compounds in 65-68% yield.