8-methyl-7,10-diphenyl-5H-benzo[h]-pyrazolo[3,4-b]quinoline-5,6(10H)-dione | 1293938-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-methyl-7,10-diphenyl-5H-benzo[h]-pyrazolo[3,4-b]quinoline-5,6(10H)-dione
• 英文别名: 8-methyl-7,10-diphenyl-10H-benzo[h]pyrazolo[3,4-b]quinoline-5,6-dione；3-methyl-1,4-diphenylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-dione；13-Methyl-11,15-diphenyl-14,15,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,11,13,16-heptaene-8,9-dione
• CAS: 1293938-96-1
• 化学式: C₂₇H₁₇N₃O₂
• 分子量: 415.451
• InChiKey: CLHHPOYZZGQNGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 2-羟基-1,4-萘醌 、 苯甲醛 在 溶剂黄146 作用下， 反应 0.33h， 以83%的产率得到8-methyl-7,10-diphenyl-5H-benzo[h]-pyrazolo[3,4-b]quinoline-5,6(10H)-dione
  参考文献：
  名称：

  A new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines

  摘要：

  建立了一种新的多组分多米诺反应，用于快速和区域选择性合成高度官能化的苯并[h]吡唑并[3,4-b]喹啉。该反应可在微波辐照下，使用易得且廉价的底物，在10-26分钟内完成。对22个例子，实现了61-91%的良好至优异的化学产率和完全的区域选择性。由于产物直接从反应溶液中沉淀出来，避免了繁琐的后处理步骤。所得苯并喹啉可通过与苯-1,2-二胺在微波辐照下反应，容易地转化为喹喉并苯并[h]异噁唑并[5,4-b]喹啉类似物。通过X射线分析，结构归属得到了含糊的确证。为此新型多组分多米诺过程提出了一种新的机理。

  DOI：

  10.1039/c1ob05034f

文献信息

• A new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines
  作者：Bo Jiang、Ge Zhang、Ning Ma、Feng Shi、Shu-Jiang Tu、Parminder Kaur、Guigen Li

  DOI：10.1039/c1ob05034f

  日期：——

  A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]pyrazolo[3,4-b]quinolines has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation within short periods of 10–26 min. Good to excellent chemical yields (61–91%) and complete regioselectivity have been achieved for 22 examples. Tedious work-up procedure can be avoided due to the direct precipitation of products from the reaction solution. The resulting benzoquinolines have been readily converted into quinoxaline-fused benzo[h]isoxazolo[5,4-b]quinoline analogues by treating with benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray analysis. A new mechanism has been proposed for this new multicomponent domino process.

  建立了一种新的多组分多米诺反应，用于快速和区域选择性合成高度官能化的苯并[h]吡唑并[3,4-b]喹啉。该反应可在微波辐照下，使用易得且廉价的底物，在10-26分钟内完成。对22个例子，实现了61-91%的良好至优异的化学产率和完全的区域选择性。由于产物直接从反应溶液中沉淀出来，避免了繁琐的后处理步骤。所得苯并喹啉可通过与苯-1,2-二胺在微波辐照下反应，容易地转化为喹喉并苯并[h]异噁唑并[5,4-b]喹啉类似物。通过X射线分析，结构归属得到了含糊的确证。为此新型多组分多米诺过程提出了一种新的机理。
• Two similarly substituted benzo[<i>h</i>]pyrazolo[3,4-<i>b</i>]quinoline-5,6(10<i>H</i>)-diones: supramolecular structures in two and three dimensions
  作者：Yurina Díaz、Jairo Quiroga、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270110018500

  日期：2010.6.15

  The molecules of 8-methyl-7,10-diphenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-dione, C(27)H(17)N(3)O(2), (I), are weakly linked into chains by a single C-H center dot center dot center dot O hydrogen bond, and these chains are linked into sheets by a pi-pi stacking interaction involving pyridyl and aryl rings. In 8-methyl-7-(4-methylphenyl)-10-phenyl-5H-benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-dione, C(28)H(19)N(3)O(2), (II), the molecules are linked into a three-dimensional framework structure by a combination of C-H center dot center dot center dot N, C-H center dot center dot center dot O and C-H center dot center dot center dot pi (arene) hydrogen bonds, together with a pi-pi stacking interaction analogous to that in (I).
• Microwave induced three-component synthesis and antimycobacterial activity of benzopyrazolo[3,4-b]quinolindiones
  作者：Jairo Quiroga、Yurina Diaz、Juan Bueno、Braulio Insuasty、Rodrigo Abonia、Alejandro Ortiz、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.ejmech.2013.12.037

  日期：2014.3

  Three series of novel 4-arylbenzo[h]pyrazolo[3,4-b]quinolin-5,6-diones 4, 7 and 9 have been efficiently obtained in good yields by three-component microwave assisted reaction between aminopyrazoles 1 or 6 (both 1-phenyl and 1-H substituted), 2-hydroxynaphthoquinone 2 and benzaldehydes 3. Compounds 4, 7 and 9 have been evaluated against fifteen Mycobacterium spp strains, and six of them have shown antimycobacterial activity. The highest inhibitory activity with MIC <= 2 mu g/mL for three of these compounds (4a, 4b and 4g) was related with their highest lipophilicity and lesser polarity within these series. (C) 2014 Elsevier Masson SAS. All rights reserved.