5-bromo-2,2-dimethyl-3H-benzofuran-4,7-dione | 583839-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-bromo-2,2-dimethyl-3H-benzofuran-4,7-dione
• 英文别名: 5-bromo-2,2-dimethyl-3H-1-benzofuran-4,7-dione
• CAS: 583839-00-3
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: ISAGYJVJSWBBJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  间戊二烯 、 5-bromo-2,2-dimethyl-3H-benzofuran-4,7-dione 在 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以77%的产率得到
  参考文献：
  名称：

  Synthesis of dihydronaphthofurandiones and dihydrofuroquinolinediones with trypanocidal activity and analysis of their stereoelectronic properties

  摘要：

  The synthesis of dihydronaphthofurandione and dihydrofuroquinolinedione derivatives 4-11 was performed through Diels-Alder reactions of dihydrobenzofurandione 1 with several carbodienes and acrolein N,N-dimethylhydrazone. Then, the use of 5-bromobenzofurandi one 2 toward 1,3-pentadiene and the 1-azadiene afforded quitiones 6 and 11 with a total regioselectivity.All the prepared quinones were tested for trypanocidal activity in vitro against Trypanosoma epimastigotes, Tulahuen strain. Among the tested compounds, the furoquinolinediones 10 and 11 have shown potent trypanocidal activities but, only the 1,5-regioisomer (11) was found active as a redox cycling agent. Calculation of their stereoelectronic properties by the density-functional theory method provided a new insight for the trypanocidal activity of these heterocyclic quinones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.046
• 作为产物：
  描述：

  呋喃酚 在 盐酸 、 manganese(IV) oxide 、 potassium nitrososulfonate 、 溴 、 sodium acetate 、 锌 作用下， 以 甲醇 、 乙醚 、 乙醇 、 氯仿 、 水 为溶剂， 反应 8.5h， 生成 5-bromo-2,2-dimethyl-3H-benzofuran-4,7-dione
  参考文献：
  名称：

  Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring

  摘要：

  The synthesis of tetracyclic quinones 10a,b, 14a,b, 19a,b and 20a,b is described. The preparations involve regioselective Diels-Alder reactions via trapping the thiazole o-quinodimethane 9 with several benzofuranquinones and benzothiophenequinones. The structure of the regioisomers was assigned through 2D NMR H-1-C-13 HMBC experiments performed on 10a and 14a. Compounds 10a,b, 14a as well as phenol I and the starting quinones 2, 5, 7 and 15 are evaluated against Leishmania sp., Toxoplasma gondii and THP-1 cells. Almost all the tested compounds exhibit significant antiprotozoal activities with lower cytotoxicities than the reference compounds. Among them, quitiones 2 and 14a possess the best activities towards L. donovani and T. gondii with the lowest toxicities. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00122-6

文献信息

• Synthesis of dihydronaphthofurandiones and dihydrofuroquinolinediones with trypanocidal activity and analysis of their stereoelectronic properties
  作者：Ricardo A. Tapia、Cristian Salas、Antonio Morello、Juan Diego Maya、Alejandro Toro-Labbé

  DOI：10.1016/j.bmc.2004.01.046

  日期：2004.5

  The synthesis of dihydronaphthofurandione and dihydrofuroquinolinedione derivatives 4-11 was performed through Diels-Alder reactions of dihydrobenzofurandione 1 with several carbodienes and acrolein N,N-dimethylhydrazone. Then, the use of 5-bromobenzofurandi one 2 toward 1,3-pentadiene and the 1-azadiene afforded quitiones 6 and 11 with a total regioselectivity.All the prepared quinones were tested for trypanocidal activity in vitro against Trypanosoma epimastigotes, Tulahuen strain. Among the tested compounds, the furoquinolinediones 10 and 11 have shown potent trypanocidal activities but, only the 1,5-regioisomer (11) was found active as a redox cycling agent. Calculation of their stereoelectronic properties by the density-functional theory method provided a new insight for the trypanocidal activity of these heterocyclic quinones. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring
  作者：Ricardo A. Tapia、Luz Alegria、Carlos D. Pessoa、Cristian Salas、Manuel J. Cortés、Jaime A. Valderrama、Marie-Elisabeth Sarciron、Félix Pautet、Nadia Walchshofer、Houda Fillion

  DOI：10.1016/s0968-0896(03)00122-6

  日期：2003.5

  The synthesis of tetracyclic quinones 10a,b, 14a,b, 19a,b and 20a,b is described. The preparations involve regioselective Diels-Alder reactions via trapping the thiazole o-quinodimethane 9 with several benzofuranquinones and benzothiophenequinones. The structure of the regioisomers was assigned through 2D NMR H-1-C-13 HMBC experiments performed on 10a and 14a. Compounds 10a,b, 14a as well as phenol I and the starting quinones 2, 5, 7 and 15 are evaluated against Leishmania sp., Toxoplasma gondii and THP-1 cells. Almost all the tested compounds exhibit significant antiprotozoal activities with lower cytotoxicities than the reference compounds. Among them, quitiones 2 and 14a possess the best activities towards L. donovani and T. gondii with the lowest toxicities. (C) 2003 Elsevier Science Ltd. All rights reserved.