15-Benzyl-14-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-10,16-diazatetracyclo[8.7.0.02,7.012,17]heptadeca-2,4,6,12,14,16-hexaen-11-one | 1628726-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 15-Benzyl-14-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-10,16-diazatetracyclo[8.7.0.02,7.012,17]heptadeca-2,4,6,12,14,16-hexaen-11-one
• 英文别名: 15-benzyl-14-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-10,16-diazatetracyclo[8.7.0.02,7.012,17]heptadeca-2,4,6,12,14,16-hexaen-11-one
• CAS: 1628726-71-5
• 化学式: C₃₃H₃₃N₃O₃
• 分子量: 519.643
• InChiKey: YBPMXFYNIKFKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  马来酸酐 、 四氢异喹啉 、 N-(3,4-dimethoxyphenylethyl)-2-isocyano-N-methyl-3-phenylpropanamide 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以27%的产率得到15-Benzyl-14-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-10,16-diazatetracyclo[8.7.0.02,7.012,17]heptadeca-2,4,6,12,14,16-hexaen-11-one
  参考文献：
  名称：

  One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition

  摘要：

  A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels-Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile -addition and finally an aza-Diels-Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles.

  DOI：

  10.1055/s-0033-1340218

文献信息

• One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition
  作者：Eduardo González-Zamora、Alejandro Islas-Jácome、Atilano Gutiérrez-Carrillo、Miguel García-Garibay

  DOI：10.1055/s-0033-1340218

  日期：——

  A rapid and efficient one-pot synthesis of a series of four novel nuevamine aza-analogues is described based on the oxidative Ugi-type reaction and aza-Diels-Alder reaction as post-functionalization. A simple IBX-mediated oxidation of a secondary amine followed by isonitrile -addition and finally an aza-Diels-Alder cycloaddition provides the desired compounds in excellent overall yields considering the short reaction time, atom economy, and the molecular complexity of the final products. This protocol presents a highly attractive procedure for the rapid generation of fused polyheterocycles.