2-(4-fluorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide | 1429923-88-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(4-fluorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide
• 英文别名: 2-[(4-fluorophenyl)methyl]-3-(4-methoxyphenyl)-2-methyl-N-quinolin-8-ylpropanamide
• CAS: 1429923-88-5
• 化学式: C₂₇H₂₅FN₂O₂
• 分子量: 428.506
• InChiKey: GIFAVVAALNSGTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(4-methoxybenzyl)-2-methylpropanoate 在 氯化亚砜 、 四甲基乙二胺 、 三乙胺 、 sodium hydroxide 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 2-(4-fluorobenzyl)-3-(4-methoxyphenyl)-2-methyl-N-(quinolin-8-yl)propanamide
  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

• 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.