6-chloro-1,3-dimethyl-9-N-propoxy-1H-pyrazolo[3,4-b]quinolin-4(9H)-one

• 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: 6-chloro-1,3-dimethyl-9-N-propoxy-1H-pyrazolo[3,4-b]quinolin-4(9H)-one
• 英文别名: 6-chloro-1,3-dimethyl-9-propoxy-1H,4H,9H-pyrazolo[3,4-b]quinolin-4-one；6-chloro-1,3-dimethyl-9-propoxypyrazolo[3,4-b]quinolin-4-one
• 化学式: C₁₅H₁₆ClN₃O₂
• 分子量: 305.764
• InChiKey: APAXIHMQFUOISM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-Dimethyl-1H-pyrazol-5-ol 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 72.0h， 生成 6-chloro-1,3-dimethyl-9-N-propoxy-1H-pyrazolo[3,4-b]quinolin-4(9H)-one
  参考文献：
  名称：

  Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d]pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors

  摘要：

  Microwave irradiation of a hydrazine and 3-methoxyacrylonitrile, ethoxymethylenemalononitrile or ethyl acetoacetate provides rapid access to 3- or 5-substituted pyrazoles in excellent yield and with total regiocontrol in a process that can be switched from one regioisomer to the other by choice of conditions. Subsequent reaction, either by microwave-assisted hydrolysis and cyclocondensation with formamide, Hantzsch-type three-component reaction with an aldehyde and ketone, or by cyclocondensation with 2-nitrobenzaldehyde, provides the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-b]pyridine or pyrazolo[3,4-b]quinolin-4-one framework, respectively, of inhibitors of mitogen-activated protein kinases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.055

文献信息

• Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d]pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors
  作者：Mark C. Bagley、Mohammed Baashen、Victoria L. Paddock、David Kipling、Terence Davis

  DOI：10.1016/j.tet.2013.07.055

  日期：2013.9

  Microwave irradiation of a hydrazine and 3-methoxyacrylonitrile, ethoxymethylenemalononitrile or ethyl acetoacetate provides rapid access to 3- or 5-substituted pyrazoles in excellent yield and with total regiocontrol in a process that can be switched from one regioisomer to the other by choice of conditions. Subsequent reaction, either by microwave-assisted hydrolysis and cyclocondensation with formamide, Hantzsch-type three-component reaction with an aldehyde and ketone, or by cyclocondensation with 2-nitrobenzaldehyde, provides the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-b]pyridine or pyrazolo[3,4-b]quinolin-4-one framework, respectively, of inhibitors of mitogen-activated protein kinases. (C) 2013 Elsevier Ltd. All rights reserved.