3-(4-nitrophenyl)-N-(quinolin-8-yl)butanamide | 1588490-19-0

• 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-nitrophenyl)-N-(quinolin-8-yl)butanamide
• CAS: 1588490-19-0
• 化学式: C₁₉H₁₇N₃O₃
• 分子量: 335.362
• InChiKey: UQNPVJPPCSZTPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.13
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-4-(4-nitrophenyl)-N-(quinolin-8-yl)butanamide 在 bis(benzonitrile)palladium(II) chloride 、 silver(I) acetate 、 sodium 2,2,2-trifluoroacetate 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 60.0h， 生成 3-(4-nitrophenyl)-N-(quinolin-8-yl)butanamide
  参考文献：
  名称：

  螯合辅助钯催化的脂肪族羧酸衍生物的γ-芳基化

  摘要：

  已经公开了钯（II）催化的脂族羧酸的高度区域选择性远程γ -C-H芳基化反应。发现8-氨基喹啉部分作为分子内双齿螯合剂适合于这种γ -C-H芳基化反应。各种芳基碘化物可成功制备出可忽略不计的二芳基化的区域选择性单芳基化产物。官能团的耐受性和易于处理的反应条件使该方法具有吸引力。

  DOI：

  10.1002/adsc.201601121

文献信息

• Pd(II)-Catalyzed Intermolecular Arylation of Unactivated C(sp³)–H Bonds with Aryl Bromides Enabled by 8-Aminoquinoline Auxiliary
  作者：Yu Wei、Huarong Tang、Xuefeng Cong、Bin Rao、Chao Wu、Xiaoming Zeng

  DOI：10.1021/ol500745t

  日期：2014.4.18

  less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)–H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)–H activation-led

  描述了在Pd（II）催化的未活化C（sp 3）-H键的分子间芳基化中使用容易获得的，反应性较低的芳基溴化物作为芳基化试剂的示例。至关重要的8-氨基喹啉基导向基团和K 2 CO 3碱促进了该反应，从而使芳基骨架可以在羧酰胺的β-位上进行区域特异性安装。通过DFT计算进行的机理研究揭示了C（sp 3）–H活化为主导的途径，该途径的特征是氧化加成为最高能量跃迁状态。
• Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp³)–H arylation
  作者：Yunyun Liu、Yi Zhang、Xiaoji Cao、Jie-Ping Wan

  DOI：10.3762/bjoc.12.108

  日期：——

  The synthesis of beta-arylated alkylamides via alkyl C-H bond arylation has been realized by means of direct one-pot reactions of acyl chlorides, aryl iodides and 8-aminoquinoline. Depending on the structure of the starting materials, both single and double beta-arylated alkylamides could be accessed.

  通过烷基氯键芳基化的β-芳基烷基酰胺的合成已经通过酰基氯，芳基碘化物和8-氨基喹啉的直接一锅反应来实现。根据原料的结构，可以使用单β-和双β-芳基烷基酰胺。
• Multicomponent reaction comprising one-pot installation of bidentate directing group and Pd(II)-catalyzed direct β-arylation of C(sp3) H bond of aliphatic and alicyclic carboxamides
  作者：Sruthi Mohan、Bojan Gopalakrishnan、Srinivasarao Arulananda Babu

  DOI：10.1016/j.tet.2016.08.010

  日期：2016.9

  To demonstrate the efficiency of the process, various bidentate directing auxiliaries were used and 8-Aminoquinoline was found to be the best directing group for accomplishing the one-pot Pd(II)-catalyzed, sp3 CH activation and β-arylation of aliphatic/alicyclic carboxamides. A variety of aliphatic/alicyclic acid chlorides and aryl iodides were used as the substrates and several β-CH arylated carboxamide

  在本文中，我们报告了一种分步经济的一锅多组分反应方案，该方案包括安装双齿指导基团（辅助），然后进行Pd（II）催化的sp 3 C H活化和各种脂肪族/脂环族酰胺的β-芳基化。因此，在Pd（OAc）2催化剂和Ag 2 CO 3添加剂存在下，脂族/脂环族酰氯，指导辅助剂的双齿（例如8-氨基喹啉）和芳基碘化物的混合物直接得到相应的产物。 β-CH芳基化N-（喹啉-8-基）羧酰胺衍生物。为了证明该方法的效率，使用了各种双齿定向助剂，发现8-氨基喹啉是完成一锅Pd（II）催化，sp 3 C H活化和脂族β-芳基化的最佳定向基团。/脂环族酰胺。多种脂族/脂环族酰氯和芳基碘化物被用作底物，并通过多组分反应策略以中等至高收率合成了几种β-CH芳基化羧酰胺衍生物。
• One-pot, solvent-free Pd(II)-catalyzed direct β-C-H arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group
  作者：Arup Dalal、Prabhakar Singh、Srinivasarao Arulananda Babu

  DOI：10.1016/j.tet.2019.01.042

  日期：2019.3

  A one-pot, multicomponent-type, solvent-free Pd(II)-catalyzed direct beta-C-H activation/arylation of carboxamides involving anhydrides as substrates via in situ installation of directing group (DG) is reported. Typically, the DG-assisted beta-C-H activation/arylation of carboxamides is a two-step process comprising the installation of DG and Pd(II)-catalyzed C-H arylation. We attempted a multicomponent-type reaction comprising an anhydride, a DG (e.g. 8-aminoquinoline), an aryl iodide in the presence of the Pd(II) catalyst and an appropriate additive. Different anhydrides, DGs, aryl iodides, catalysts and additives were screened to reveal the scope of this multicomponent-type C-H arylation reaction process and various beta-C-H arylated carboxamides were obtained in satisfactory to good yields. (C) 2019 Elsevier Ltd. All rights reserved.