2,2-二甲基-2,3-二氢苯并呋喃-4,7-二酮 | 84428-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2,2-二甲基-2,3-二氢苯并呋喃-4,7-二酮
• 英文名称: 2,2-dimethyl-2,3-dihydrobenzofuran-4,7-dione
• 英文别名: 2,2-dimethylbenzofuran-4,7(2H,3H)-dione；2,2-dimethyl-3H-1-benzofuran-4,7-dione
• CAS: 84428-21-7
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: DIUSMPZLXXRDMS-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  270.8±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 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：

  2,2-二甲基-2,3-二氢苯并呋喃-4,7-二酮 在 palladium 10% on activated carbon 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 2,3-dihydro-2,2-dimethyl benzofuran-4,7-diol
  参考文献：
  名称：

  WO2006/66183

  摘要：

  公开号：
• 作为产物：
  描述：

  呋喃酚 在 potassium nitrososulfonate 、 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2,2-二甲基-2,3-二氢苯并呋喃-4,7-二酮
  参考文献：
  名称：

  Brown, Roger F. C.; Fallon, Gary D.; Gatehouse, Bryan M., Australian Journal of Chemistry, 1982, vol. 35, # 8, p. 1665 - 1678

  摘要：

  DOI：

文献信息

• A Synthetic Approach to (±)-Tridentoquinone
  作者：RFC Brown、AJ Robinson

  DOI：10.1071/ch9950515

  日期：——

  Synthesis of the ansa-bridged benzofuranquinone (�)- tridentoquinone (�)-(1) is approached by construction of a C4 methyl ketone chain at the 3-position of 6-bromo-4,5,7-trimethoxy-2,2-dimethyl-2,3-dihydrobenzofuran (10) and alkylation at its 6-position leading after modification to a dimethyl C10 aldehydic chain. Closure of the ansa bridge by McMurry coupling of the aldehyde and ketone groups of the intermediate (33) with C8K/TiCl3 appears to occur, but in poor yield and with uncertain stereochemistry, and the synthesis has not been completed.

  通过在 6-溴-4,5,7-三甲氧基-2,2-二甲基-2,3-二氢苯并呋喃 (10) 的 3-位上构建 C4 甲基酮链，并在其 6-位上进行烷基化，从而在改性后形成二甲基 C10 醛链，从而合成了ansa-bridged benzofuranquinone (�)- tridentoquinone (�)-(1) 。通过 C8K/TiCl3 与中间体（33）的醛基和酮基的麦克莫里偶联，似乎可以封闭安萨桥，但收率低，立体化学性质不确定，合成尚未完成。
• Direct Access to 1,4-Dihydroxyanthraquinones:  The Hauser Annulation Reexamined with <i>p</i>-Quinones
  作者：Dipakranjan Mal、Sutapa Ray、Indrajeet Sharma

  DOI：10.1021/jo062271j

  日期：2007.6.1

  3-Phenylsulfanylphthalides (e.g. 8a) readily react with p-benzoquinones in the presence of (LiOBu)-Bu-t in THF to furnish 1,4-dihydroxyanthraquinones in good yields and one-pot operations.
• 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.
• [EN] NOVEL SAFRAMYCIN ANALOGS AS THERAPEUTIC AGENTS<br/>[FR] NOUVEAUX ANALOGUES DE SAFRAMYCINE UTILISES EN TANT QU'AGENTS THERAPEUTIQUES
  申请人：AXYS PHARM INC

  公开号：WO2006066183A2

  公开（公告）日：2006-06-22

  [EN] The present invention is directed to saframcyin analogs that are useful in the treatment of cancer. Pharmaceutical compositions and processes for preparing these compounds are also disclosed.
  [FR] L'invention concerne des analogues de saframycine utilisés dans le traitement du cancer. L'invention concerne également des compositions pharmaceutiques et des procédés de préparation desdits composés.