2-甲基-1-苯并呋喃-4,7-二酮 | 138518-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-1-苯并呋喃-4,7-二酮
• 英文名称: 2-methylbenzofuran-4,7-dione
• 英文别名: 2-methylbenzofuran-4,7-dione；2-methyl-1-benzofuran-4,7-dione
• CAS: 138518-17-9
• 化学式: C₉H₆O₃
• 分子量: 162.145
• InChiKey: OUJAGRAMAGJLNH-UHFFFAOYSA-N

物化性质

• 沸点：
  321.2±42.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-1-苯并呋喃-4,7-二酮 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.42h， 生成 2-methyl-4,5,6,7,8,9-hexahydrofuro<2,3-g>quinoline-4,9-dione-8-spiro-4'-cyclohexa-2',5'-dien-1'-one
  参考文献：
  名称：

  Kita, Yasuyuki; Tohma, Hirofumi; Inagaki, Masanao, Journal of the American Chemical Society, 1992, vol. 114, # 6, p. 2175 - 2180

  摘要：

  DOI：
• 作为产物：
  描述：

  4-hydroxy-2-methylbenzofuran 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以74%的产率得到2-甲基-1-苯并呋喃-4,7-二酮
  参考文献：
  名称：

  区域特异性异Diels-Alder合成呋喃[2,3- g ]和呋喃[3,2- g ]喹啉-4,9-二酮

  摘要：

  的5-或6-溴苯并呋喃-4,7-二酮的Diels-Alder反应7或10朝向azadienes 1得到regiospe-cifically呋喃并[2,3克]或呋喃并[3,2-克]喹啉-4,9-二二酮3或4。通过2D NMR 1 H- 13 H HMBC实验进行的区域异构体的分配表明，环加成物的区域化学在溴原子位置的控制下。由HOMO和azadienes的LUMO轨道系数的半经验方法PM3计算1和醌2表明，较大的位于在C-4 1和C-5为2。

  DOI：

  10.1016/0040-4020(96)00484-x

文献信息

• 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.
• quinonic derivatives active against a virulent strain of toxoplasma gondii . synthesis of 2-methylfuro[2,3- g ]- and [3,2- g ]isoquinolinetriones
  作者：Pascal Nebois、Marie-Elizabeth Sarciron、Brigitte Bibal、Boufelja Bouammali、Omar Cherkaoui、Félix Pautet、Anne-Françoise Pétavy、Nadia Walchshofer、Houda Fillion

  DOI：10.1016/s0960-894x(00)00112-8

  日期：2000.5

  2-methylfuro[2,3-g]isoquinoline-4,7,9-trione (4) and 2-methylfuro[3,2-g]isoquinoline-4,6,9-trione (5) were prepared regiospecifically from 2-azadiene 9 and bromobenzofuran-4,7-diones 1 or 11. The activity of these two compounds and some other quinonic derivatives was evaluated in vitro against a virulent strain of Toxoplasma gondii. Compounds 4 and 7 were found to be as active as pyrimethamine. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Kita, Yasuyuki; Tohma, Hirofumi; Inagaki, Masanao, Journal of the American Chemical Society, 1992, vol. 114, # 6, p. 2175 - 2180
  作者：Kita, Yasuyuki、Tohma, Hirofumi、Inagaki, Masanao、Hatanaka, Kenji、Yakura, Takayuki

  DOI：——

  日期：——
• Regiospecific hetero Diels-Alder synthesis of furo[2,3-g] and furo[3,2-g]quinoline-4,9-diones
  作者：Omar Cherkaoui、Pascal Nebois、Houda Fillion、Monique Domard、Bernard Fenet

  DOI：10.1016/0040-4020(96)00484-x

  日期：1996.7

  Diels-Alder reactions of 5- or 6-bromobenzofuran-4,7-diones 7 or 10 towards azadienes 1 afford regiospe-cifically furo[2,3-g] or furo[3,2-g]quinoline-4,9-diones 3 or 4. Assignment of the regioisomers, made by 2D NMR 1H-13H HMBC experiments, showed that the regiochemistry of the cycloadditions is under control of the bromine atom position. Calculations by the semiempirical method PM3 of the HOMO and

  的5-或6-溴苯并呋喃-4,7-二酮的Diels-Alder反应7或10朝向azadienes 1得到regiospe-cifically呋喃并[2,3克]或呋喃并[3,2-克]喹啉-4,9-二二酮3或4。通过2D NMR 1 H- 13 H HMBC实验进行的区域异构体的分配表明，环加成物的区域化学在溴原子位置的控制下。由HOMO和azadienes的LUMO轨道系数的半经验方法PM3计算1和醌2表明，较大的位于在C-4 1和C-5为2。