2-n-propyl-5,10-dimethoxy-1,4-dihydrobenz[g]isoquinolin-3(2H)-one | 933774-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-n-propyl-5,10-dimethoxy-1,4-dihydrobenz[g]isoquinolin-3(2H)-one
• 英文别名: 5,10-Dimethoxy-2-propyl-1,4-dihydrobenzo[g]isoquinolin-3-one
• CAS: 933774-05-1
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: LYVXAVOOWBYYDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-n-propyl-5,10-dimethoxy-1,4-dihydrobenz[g]isoquinolin-3(2H)-one 在 ammonium cerium(IV) nitrate 、 air 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 2-n-propylbenzo[g]isoquinoline-3,5,10(2H)-trione
  参考文献：
  名称：

  New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones

  摘要：

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.052
• 作为产物：
  描述：

  ethyl (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetate 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 tin(ll) chloride 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 丙酮 为溶剂， 反应 20.5h， 生成 2-n-propyl-5,10-dimethoxy-1,4-dihydrobenz[g]isoquinolin-3(2H)-one
  参考文献：
  名称：

  New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones

  摘要：

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.052

文献信息

• New synthesis of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones
  作者：Jan Jacobs、Sven Claessens、Bart Kesteleyn、Kris Huygen、Norbert De Kimpe

  DOI：10.1016/j.tet.2006.12.052

  日期：2007.3

  Various N-substituted benz[g]isoquinoline-3,5,10(2H)-triones 7 were prepared starting from vitamin K-3 (menadione) 9. The key steps involve substitution of a benzylic bromide by a primary amine and intramolecular condensation across the ester moiety of a (3-bromo-methyl -naphth-2-yl) acetate 8 followed by oxidation with cerium(IV) ammonium nitrate (CAN) and spontaneous dehydrogenation, resulting in the title compounds 7. A selection of the synthesised new compounds was tested in vitro against Mycobacterium tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.