3,4-dibutyl-1-methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile | 1235712-74-9

• 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-2-oxo-1,2-dihydroquinoline-6-carbonitrile
• 英文别名: 3,4-Dibutyl-1-methyl-2-oxoquinoline-6-carbonitrile
• CAS: 1235712-74-9
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: LJRYCHDRHDPODV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methyl-N-(4-cyanophenyl)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59%的产率得到3,4-dibutyl-1-methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile
  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 aerobic oxidative cyclization of anilines, alkynes, and CO
  作者：Xinyao Li、Jun Pan、Hao Wu、Ning Jiao

  DOI：10.1039/c7sc02181j

  日期：——

  Transition-metal-catalyzed oxidative C-H cyclization of anilines has been an attractive and powerful strategy for the efficient construction of N-heterocycles. However, the primary and tertiary anilines are rarely employed in this strategy due to the relatively unstability with strong oxidants or the presence of three C-N bonds. By using aerobic oxidative protocol, we describe here a novel Rh-catalyzed

  苯胺的过渡金属催化的氧化 CH 环化已成为有效构建 N-杂环的有吸引力且有效的策略。然而，由于与强氧化剂相对不稳定或存在三个CN键，伯苯胺和叔苯胺很少用于该策略。通过使用有氧氧化协议，我们在这里描述了一种新颖的 Rh 催化 CH 环化各种苯胺与炔烃和 CO。特别是，简单的伯苯胺和通过 CN 键裂解容易制备的叔苯胺可以很容易地转化为 quinolin-2 (1H)-ones，它们是高附加值、具有生物学意义的 N-杂环化合物。
• 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.