5-methyl-1,3-diphenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one | 109334-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methyl-1,3-diphenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one
• 英文别名: 5-methyl-1,3-diphenyl-1,5-dihydropyrazolo[4,3-c]quinolin-4-one；5-methyl-1,3-diphenyl-1H-pyrazolo[4,3-c]quinolin-4(5H)-one；5-Methyl-1,3-diphenylpyrazolo[4,3-c]quinolin-4-one
• CAS: 109334-75-0
• 化学式: C₂₃H₁₇N₃O
• 分子量: 351.407
• InChiKey: RMZKGCVSKNPPIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-1,3-diphenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one 、 硫酸二甲酯 生成
  参考文献：
  名称：

  Regioselective synthesis of 2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-ones by the cyclization of 3-acyl-4-methoxy-1-methylquinolinones with hydrazines

  摘要：

  Reaction of 3-acyl-4-methoxy-1-methylquinolinones 2 and 5 with hydrazines has been investigated Under different experimental conditions. Compound 2 always gave rise selectively and exclusively to the regioisomeric 1,3-disubstituted- or 2,3-disubstituted-pyrazolo[4,3-c]quinolin-4(5H)one (compounds 3a,b or 4a,b, respectively), while reaction of 5 with N-methylhydrazine led to a mixture of pyrazoles 7a and 8a. With N-pheny1hydrazine, compounds 7b or 8b were regioselectively obtained. Compound 8a could be selectively synthesized working in solventless conditions. Structural elucidation of all products was independently achieved by NMR spectroscopy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.028
• 作为产物：
  描述：

  ethyl (2-nitrobenzoyl)benzoylacetate 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 5-methyl-1,3-diphenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one
  参考文献：
  名称：

  1,3-二芳基吡唑并[4,5-c]-和-[5,4-c]喹啉-4-酮。4.苯并二氮杂receptor受体结合的合成和特异性抑制。

  摘要：

  制备了一系列的1,3-二芳基吡唑并[4,5-c]-和-[5,4-c]喹啉-4-酮，并测试了它们从牛脑膜上置换[3H]氟硝西epa的能力。虽然1，3-二芳基吡唑并[4，5-c]喹啉衍生物对受体位点具有亲和力，但它们的[5，4-c]异构体却没有结合活性。

  DOI：

  10.1021/jm00393a009

文献信息

• Nouvelle voie de synthese d'arylpyrazolo -[4,3-c]-quinoleines via la cycloaddition dipolaire −1,3
  作者：Boujemâa Daou、Mohamed Soufiaoui

  DOI：10.1016/s0040-4020(01)81014-0

  日期：1989.1

  inverse regiospecificity is observed comparatively to the one established for the N-methylindole and N-ethylindole. To establish that regiospecificity chemically, we synthetised furthers arylpyrazolo - [4,3-c] -quinolines by using the Friedländer condensation.

  已通过光谱和化学方法证明了二芳基亚硝胺（DANI）对杂环（如苯并呋喃和N-甲基吲哚）的区域特异性。与在吲哚核的2位具有烷氧基羰基官能团的N-烷基吲哚相比，对于N-甲基吲哚和N-乙基吲哚所确定的反向烷基特异性被观察到。为了通过化学方法确定该区域特异性，我们使用Friedländer缩合反应进一步合成了芳基吡唑并-[4,3-c]-喹啉。
• Synthesis of Pyrazolo[4,3-<i>c</i>]quinolin-4-ones and Indolo[3,2-<i>c</i>]quinolin-6-ones by the Photocyclization of <i>N</i>-Aryl-<i>o</i>-chloroheteroarenecarboxamides
  作者：Wei Zhang、Shenci Lu、Jinhui Pan、Jie Zhang

  DOI：10.1055/s-2008-1067013

  日期：2008.5

  An efficient synthesis of pyrazolo[4,3- C]quinolin-4-ones and indolo[3,2- C]quinolin-6-ones has been achieved by the photocyclization of 5-chloro- N-phenyl-1 H-pyrazole-4-carboxamides and 2-chloro- N-phenyl-1 H-indole-3-carboxamides in acetone.

  5-氯-N-苯基-1 H-吡唑光环化高效合成吡唑并[4,3-C]喹啉-4-酮和吲哚[3,2-C]喹啉-6-酮丙酮中的 -4-羧酰胺和 2-氯-N-苯基-1 H-吲哚-3-羧酰胺。
• Stadlbauer, Wolfgang; Hojas, Gerhard, Journal of Heterocyclic Chemistry, 2004, vol. 41, # 5, p. 681 - 690
  作者：Stadlbauer, Wolfgang、Hojas, Gerhard

  DOI：——

  日期：——
• PALAZZINO, GIOVANNA;CECCHI, LUCIA;MELANI, FABRIZIO;COLOTTA, VITTORIA;FILA+, J. MED. CHEM., 30,(1987) N 10, 1737-1742
  作者：PALAZZINO, GIOVANNA、CECCHI, LUCIA、MELANI, FABRIZIO、COLOTTA, VITTORIA、FILA+

  DOI：——

  日期：——
• 1,3-Diarylpyrazolo[4,5-c]- and -[5,4-c]quinolin-4-ones. 4. Synthesis and specific inhibition of benzodiazepine receptor binding
  作者：Giovanna Palazzino、Lucia Cecchi、Fabrizio Melani、Vittoria Colotta、Guido Filacchioni、Claudia Martini、Antonio Lucacchini

  DOI：10.1021/jm00393a009

  日期：1987.10

  4-c]quinolin-4-ones were prepared and tested for their ability to displace [3H]flunitrazepam from bovine brain membranes. While the 1,3-diarylpyrazolo[4,5-c]quinoline derivatives showed affinity for the receptor site, their [5,4-c] isomers were devoid of binding activity.

  制备了一系列的1,3-二芳基吡唑并[4,5-c]-和-[5,4-c]喹啉-4-酮，并测试了它们从牛脑膜上置换[3H]氟硝西epa的能力。虽然1，3-二芳基吡唑并[4，5-c]喹啉衍生物对受体位点具有亲和力，但它们的[5，4-c]异构体却没有结合活性。