2-isobutylbenzo[g]isoquinoline-3,5,10(2H)-trione | 933774-21-1

• 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-isobutylbenzo[g]isoquinoline-3,5,10(2H)-trione
• 英文别名: 2-(2-Methylpropyl)benzo[g]isoquinoline-3,5,10-trione；2-(2-methylpropyl)benzo[g]isoquinoline-3,5,10-trione
• CAS: 933774-21-1
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: YQEAUXXRBQGOKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isobutylbenzo[g]isoquinoline-3,5,10(2H)-trione 、 氰化钾 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到4-cyano-2-isobutylbenz[g]isoquinoline-3,5,10(2H)-trione
  参考文献：
  名称：

  First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones

  摘要：

  Structural modifications to the benz[g]isoquinoline skeleton of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were envisaged in order to make future SAR studies possible for this type of bioactive compounds. Several N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were converted to novel 2,4-substituted benz[g]isoquinoline-3,5,10(2H)-tiiones, new tetracyclic 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones. All the synthesized target compounds represent new heterocyclic systems, which were previously undescribed in the literature. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.111
• 作为产物：
  描述：

  ethyl (3-bromomethyl-1,4-dimethoxynaphthalen-2-yl)acetate 在 ammonium cerium(IV) nitrate 、 air 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 2-isobutylbenzo[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

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.
• First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones
  作者：Jan Jacobs、Bart Kesteleyn、Norbert De Kimpe

  DOI：10.1016/j.tet.2008.05.111

  日期：2008.8

  Structural modifications to the benz[g]isoquinoline skeleton of N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were envisaged in order to make future SAR studies possible for this type of bioactive compounds. Several N-substituted benz[g]isoquinoline-3,5,10(2H)-triones were converted to novel 2,4-substituted benz[g]isoquinoline-3,5,10(2H)-tiiones, new tetracyclic 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones. All the synthesized target compounds represent new heterocyclic systems, which were previously undescribed in the literature. (C) 2008 Elsevier Ltd. All rights reserved.