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

• 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.
• 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).