N-(quinolin-8-yl)-3-(m-tolyl)butanamide | 1215018-92-0

• 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: N-(quinolin-8-yl)-3-(m-tolyl)butanamide
• 英文别名: 3-(3-methylphenyl)-N-quinolin-8-ylbutanamide
• CAS: 1215018-92-0
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: LZICDLZRBMIJBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(quinolin-8-yl)-3-(m-tolyl)butanamide 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到3-(m-tolyl)butanoic acid
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2019.01.042
• 作为产物：
  描述：

  间碘甲苯 、 N-(quinolin-8-yl)butyramide 在 cesium phosphate 、 palladium diacetate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 7.0h， 以79%的产率得到N-(quinolin-8-yl)-3-(m-tolyl)butanamide
  参考文献：
  名称：

  Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp² and sp³ Carbon−Hydrogen Bonds

  摘要：

  We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.

  DOI：

  10.1021/ja910900p

文献信息

• 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。
• Direct Arylation of Primary and Secondary sp³ C–H Bonds with Diarylhyperiodonium Salts via Pd Catalysis
  作者：Fei Pan、Peng-Xiang Shen、Li-Sheng Zhang、Xin Wang、Zhang-Jie Shi

  DOI：10.1021/ol402116a

  日期：2013.9.20

  Palladium-catalyzed primary and secondary sp3 C–H bond arylation is reported. The method using diarylhyperiodonium salts as arylation reagents shows good functional group tolerance and proceeds under mild reaction conditions. The KIE experiments show that the C–H bond activation is the rate-determining step.

  据报道钯催化的第一级和第二级sp 3 C–H键芳基化。使用二芳基高碘鎓盐作为芳基化试剂的方法显示出良好的官能团耐受性，并且在温和的反应条件下进行。KIE实验表明，CH键的活化是决定速率的步骤。
• Palladium-Catalyzed Cs₂CO₃-Promoted Arylation of Unactivated C(sp³)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation
  作者：Quan Gou、Zhao-Fu Zhang、Zhi-Cheng Liu、Jun Qin

  DOI：10.1021/acs.joc.5b00111

  日期：2015.3.20

  PdCl2(CH3CN)(2)-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.
• ANTI-HCMV COMPOSITIONS AND METHODS
  申请人：FORGE Life Science, LLC

  公开号：US20180170884A1

  公开（公告）日：2018-06-21

  This document relates to compounds useful as agents for preventing or treating human cytomegalovirus (HCMV) infections.
• 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.