3,4-dibutyl-1-methyl-6-nitroquinolin-2(1H)-one | 1235712-73-8

• 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: 3,4-dibutyl-1-methyl-6-nitroquinolin-2(1H)-one
• 英文别名: 3,4-Dibutyl-1-methyl-6-nitroquinolin-2-one
• CAS: 1235712-73-8
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: QNWOPDGYXWGNSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-methyl-N-(4-nitrophenyl)carbamoyl chloride 、 5-癸炔 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,5-环辛二烯 作用下， 以 邻二甲苯 为溶剂， 反应 20.0h， 以73%的产率得到3,4-dibutyl-1-methyl-6-nitroquinolin-2(1H)-one
  参考文献：
  名称：

  Iridium-Catalyzed Annulation of N-Arylcarbamoyl Chlorides with Internal Alkynes

  摘要：

  An iridium complex successfully catalyzed the annulation of various N-arylcarbamoyl chlorides with internal alkynes to afford 2-quinolones in good to excellent yields. The present reaction is widely applicable to substrates with various functionalities. An amide-iridacycle complex was isolated, and it is likely that such an iridacycle species is a key intermediate in the catalytic reaction.

  DOI：

  10.1021/ja104153k

文献信息

• Rh-Catalyzed Construction of Quinolin-2(1<i>H</i>)-ones via C–H Bond Activation of Simple Anilines with CO and Alkynes
  作者：Xinyao Li、Xinwei Li、Ning Jiao

  DOI：10.1021/jacs.5b05843

  日期：2015.7.29

  A novel and efficient Rh-catalyzed Carbonylation and annulation of simple anilines with CO and alkynes through N-H and CH bond activation for the direct synthesis of quinolin-2(1H)-ones has been developed. Simple anilines without preactivation, broad substrate scope with hetero/polycycles, and high-value products make this protocol very-practical and attractive. A key rhodacycle complex was isolated and well-characterized.
• Iridium-Catalyzed Annulation of <i>N</i>-Arylcarbamoyl Chlorides with Internal Alkynes
  作者：Tomohiro Iwai、Tetsuaki Fujihara、Jun Terao、Yasushi Tsuji

  DOI：10.1021/ja104153k

  日期：2010.7.21

  An iridium complex successfully catalyzed the annulation of various N-arylcarbamoyl chlorides with internal alkynes to afford 2-quinolones in good to excellent yields. The present reaction is widely applicable to substrates with various functionalities. An amide-iridacycle complex was isolated, and it is likely that such an iridacycle species is a key intermediate in the catalytic reaction.