2-(4-methoxybenzyl)-2-methyl-N-(quinolin-8-yl)butanamide | 1429896-44-5

• 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: 2-(4-methoxybenzyl)-2-methyl-N-(quinolin-8-yl)butanamide
• 英文别名: 2-[(4-methoxyphenyl)methyl]-2-methyl-N-quinolin-8-ylbutanamide
• CAS: 1429896-44-5
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: FBMKNNYTIWSHNT-UHFFFAOYSA-N

物化性质

• 沸点：
  572.8±35.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-二甲基丁酸 在 氯化亚砜 、 四甲基乙二胺 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 2-(4-methoxybenzyl)-2-methyl-N-(quinolin-8-yl)butanamide
  参考文献：
  名称：

  β-Arylation of Carboxamides via Iron-Catalyzed C(sp³)–H Bond Activation

  摘要：

  A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.

  DOI：

  10.1021/ja402806f

文献信息

• Nickel-catalyzed chelation-assisted direct arylation of unactivated C(sp³)–H bonds with aryl halides
  作者：Mingliang Li、Jiaxing Dong、Xiaolei Huang、Kaizhi Li、Qian Wu、Feijie Song、Jingsong You

  DOI：10.1039/c4cc00716f

  日期：——

  this work, we have disclosed the nickel-catalyzed unactivated beta-C(sp(3))-H bond arylation of aliphatic acid derivatives with aryl iodides/bromides via bidentate chelation-assistance of an 8-aminoquinoline moiety. These preliminary results indicate the intrinsic catalytic potential of nickel metal for unactivated C(sp(3))-H bond arylation.

  在这项工作中，我们通过8-氨基喹啉部分的双齿螯合辅助，公开了脂肪酸衍生物与芳基碘化物/溴化物的镍催化未活化的β-C（sp（3））-H键芳基化。这些初步结果表明未激活的C（sp（3））-H键芳基化的镍金属的固有催化潜力。
• β-Arylation of Carboxamides via Iron-Catalyzed C(sp³)–H Bond Activation
  作者：Rui Shang、Laurean Ilies、Arimasa Matsumoto、Eiichi Nakamura

  DOI：10.1021/ja402806f

  日期：2013.4.24

  A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.