3-(4-bromophenyl)-N-(quinolin-8-yl)butanamide | 1453491-79-6

• 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-bromophenyl)-N-(quinolin-8-yl)butanamide
• 英文别名: 3-(4-bromophenyl)-N-quinolin-8-ylbutanamide
• CAS: 1453491-79-6
• 化学式: C₁₉H₁₇BrN₂O
• 分子量: 369.261
• InChiKey: CCCYRIOUEAYFJL-UHFFFAOYSA-N

物化性质

• 熔点：
  81-83 °C
• 沸点：
  580.4±35.0 °C(predicted)
• 密度：
  1.417±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  8-氨基喹啉 在 双(乙腈)氯化钯(II) 、 草酰氯 、 cesium acetate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 均三甲苯 为溶剂， 反应 6.0h， 生成 3-(4-bromophenyl)-N-(quinolin-8-yl)butanamide
  参考文献：
  名称：

  钯催化碱促进芳基碘对未活化 C(sp3)-H 键的芳基化：合成 β-芳基羧酸衍生物的实用方法

  摘要：

  开发了一种高效的方案，用于在 PdCl2(CH3CN)2/CsOAc 催化下芳基碘化物对羧酰胺进行 β-芳基化。发现该方法可耐受广泛的底物，并成功用于制备各种 β-芳基 α-氨基和 γ-氨基酸衍生物。这种方法的效用在精神药物 (±)-phenibut 和 β-芳基胆汁酸类似物的合成中得到了进一步说明。

  DOI：

  10.1002/ejoc.201701215

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。
• 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.