1-(2-methoxyquinolin-3-yl)-2-(5-methyl-2-nitrophenyl)ethanol | 796854-70-1

• 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: 1-(2-methoxyquinolin-3-yl)-2-(5-methyl-2-nitrophenyl)ethanol
• CAS: 796854-70-1
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: HTVDOTCKQCQWCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  522.9±50.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-methoxyquinolin-3-yl)-2-(5-methyl-2-nitrophenyl)ethanol 在 Raney Nickel 2800 (H₂O) 氢气 作用下， 以 四氢呋喃 为溶剂， 65.0 ℃ 、275.79 kPa 条件下， 反应 6.0h， 以58%的产率得到2-(2-amino-5-methylphenyl)-1-(2-methoxyquinolin-3-yl)ethanol
  参考文献：
  名称：

  通过邻硝基苄基羰基化合物的催化还原环化合成新型KDR激酶抑制剂

  摘要：

  通过容易获得的苯乙醇类似物的Swern型氧化证明了邻硝基苄基羰基化合物的有效合成。使用催化阮内镍对邻硝基苄基羰基3进行还原环化，可得到1 H-吲哚-2-基-1 H-喹啉2，产率为95％。2的水解可定量提供KDR激酶抑制剂1。描述了还原环化反应的检查和条件的优化。

  DOI：

  10.1021/jo048843m
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 氢氧化钾 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 醋酸异丙酯 为溶剂， 反应 3.0h， 生成 1-(2-methoxyquinolin-3-yl)-2-(5-methyl-2-nitrophenyl)ethanol
  参考文献：
  名称：

  Synthesis of 5-Substituted-1H-indol-2-yl-1H-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors

  摘要：

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.

  DOI：

  10.1021/jo0480545

文献信息

• Synthesis of Novel KDR Kinase Inhibitors through Catalytic Reductive Cyclization of <i>o</i>-Nitrobenzylcarbonyl Compounds
  作者：Audrey Wong、Jeffrey T. Kuethe、Ian W. Davies、David L. Hughes

  DOI：10.1021/jo048843m

  日期：2004.10.1

  through the Swern-type oxidation of readily accessible phenethanol analogues. Reductive cyclization of o-nitrobenzylcarbonyl 3 using catalytic Raney nickel gives 1H-indol-2-yl-1H-quinoline 2 in 95% yield. Hydrolysis of 2 affords the KDR kinase inhibitor 1 in quantitative yield. The examination of the reductive cyclization reaction and optimization of conditions is described.

  通过容易获得的苯乙醇类似物的Swern型氧化证明了邻硝基苄基羰基化合物的有效合成。使用催化阮内镍对邻硝基苄基羰基3进行还原环化，可得到1 H-吲哚-2-基-1 H-喹啉2，产率为95％。2的水解可定量提供KDR激酶抑制剂1。描述了还原环化反应的检查和条件的优化。
• Synthesis of 5-Substituted-1<i>H</i>-indol-2-yl-1<i>H</i>-quinolin-2-ones:  A Novel Class of KDR Kinase Inhibitors
  作者：Jeffrey T. Kuethe、Audrey Wong、Chuanxing Qu、Jacqueline Smitrovich、Ian W. Davies、David L. Hughes

  DOI：10.1021/jo0480545

  日期：2005.4.1

  A number of approaches for the synthesis of the 1H-indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitor 1 are described. The preparation and reaction of trimethylsilylnitrobenzene 26 with 2-methoxy-3-quinolinecarboxaldehyde 28 afforded alcohol 30, which was the key intermediate for the preparation of the target compounds. Conversion of alcohol 30 to either nitroketone 36 or nitrostyrene 45 set the stage for reductive cyclization and the formation of indole 25. The quinolin-2-one functionality was unmasked in the last step to provide compound 1 in 56-60% overall yield from readily available starting materials.