3,4-dibutyl-1-methylquinolin-2(1H)-one | 1235712-44-3

• 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-methylquinolin-2(1H)-one
• 英文别名: 3,4-Dibutyl-1-methylquinolin-2-one；3,4-dibutyl-1-methylquinolin-2-one
• CAS: 1235712-44-3
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: JPZPNNAHVNWJJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-癸炔 、 (N-methylanilino)methanone;rhodium(3+);triphenylphosphane;acetate 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以74%的产率得到3,4-dibutyl-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Rh-Catalyzed Construction of Quinolin-2(1H)-ones via C–H Bond Activation of Simple Anilines with CO and Alkynes

  摘要：

  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.

  DOI：

  10.1021/jacs.5b05843

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。
• Iridium-Catalyzed Carbonylative Synthesis of Halogen-Containing Quinolin-2(1<i>H</i>)-ones from Internal Alkynes and Simple Anilines
  作者：Fengxiang Zhu、Yahui Li、Zechao Wang、Xiao-Feng Wu

  DOI：10.1002/adsc.201600680

  日期：2016.11.3

  straightforward synthesis of halogen‐containing quinolin‐2(1H)‐ones. The reaction proceeds without preactivation and directing groups through direct N–H and C–H bond activation with a broad substrate scope and high efficiency. Halogen functional groups can be well tolerated here. Remarkably, this is the first example of an iridium‐catalyzed carbonylative C–H activation of anilines.

  喹啉2（1 H）-1是重要的化学药品，在制药中有多种应用。在本文中，我们开发了一种新颖且有效的铱催化的带有内部炔烃的简单苯胺的羰基环化反应，可直接合成含卤素的喹啉-2（1 H）-酮。反应在没有预活化的情况下进行，并通过直接的N–H和C–H键活化来引导基团，具有广泛的底物范围和高效率。此处可以很好地耐受卤素官能团。值得注意的是，这是铱催化苯胺的羰基CH活化的第一个例子。
• Ligand-Enabled Ni–Al Bimetallic Catalysis for Nonchelated Dual C–H Annulation of Arylformamides and Alkynes
  作者：Yin-Xia Wang、Feng-Ping Zhang、Yu-Xin Luan、Mengchun Ye

  DOI：10.1021/acs.orglett.0c00432

  日期：2020.3.20

  A bifunctional secondary phosphine oxide (SPO) ligand-controlled method was developed for Ni-Al-catalyzed nonchelated dual C-H annulation of arylformamides with alkynes, providing a series of substituted amide-containing heterocycles in <= 97% yield. The SPO-bound bimetallic catalysis proved to be critical to the reaction efficiency.
• 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.
• 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.