ethyl (3-bromomethyl-1,4-dimethoxynaphthalen-2-yl)acetate | 933774-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl (3-bromomethyl-1,4-dimethoxynaphthalen-2-yl)acetate
• 英文别名: Ethyl 2-[3-(bromomethyl)-1,4-dimethoxynaphthalen-2-yl]acetate
• CAS: 933774-01-7
• 化学式: C₁₇H₁₉BrO₄
• 分子量: 367.239
• InChiKey: VOEIUVUNKDVSTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (1,4-dimethoxy-3-methylnaphthalen-2-yl)acetic acid 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 ethyl (3-bromomethyl-1,4-dimethoxynaphthalen-2-yl)acetate
  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.