3-phenyl-N-(quinolin-8-yl)hexanamide | 1453491-72-9

• 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-phenyl-N-(quinolin-8-yl)hexanamide
• 英文别名: 3-phenyl-N-quinolin-8-ylhexanamide
• CAS: 1453491-72-9
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: CDBOSCWZDVETIW-UHFFFAOYSA-N

物化性质

• 沸点：
  543.5±33.0 °C(predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基碘三氟甲烷磺酸盐 、 8-(N-(n-hexanoyl)amino)quinoline 在 Pd[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](OAc)2 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以90%的产率得到3-phenyl-N-(quinolin-8-yl)hexanamide
  参考文献：
  名称：

  通过Pd催化用二芳基高碘鎓盐直接将伯和仲sp 3 C–H键芳基化

  摘要：

  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。

  DOI：

  10.1021/ol402116a

文献信息

• 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。
• 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.
• 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。