2-(4-methoxyphenyl)-4-phenyl-6-(thiophen-2-yl)pyridine | 1428423-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-methoxyphenyl)-4-phenyl-6-(thiophen-2-yl)pyridine
• 英文别名: 2-(4-Methoxyphenyl)-4-phenyl-6-thiophen-2-ylpyridine；2-(4-methoxyphenyl)-4-phenyl-6-thiophen-2-ylpyridine
• CAS: 1428423-42-0
• 化学式: C₂₂H₁₇NOS
• 分子量: 343.449
• InChiKey: DHXNQBLFKCTAFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-噻吩)乙胺 、 3-(4-甲氧基苯基)-1-苯丙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 13.0h， 以83%的产率得到2-(4-methoxyphenyl)-4-phenyl-6-(thiophen-2-yl)pyridine
  参考文献：
  名称：

  Base-Promoted β-C(sp³)–H Functionalization of Enaminones: An Approach to Polysubstituted Pyridines

  摘要：

  A convenient "one-pot" base-promoted synthesis of polysubstituted pyridines from 1-arylethylamines and ynones through the direct beta-C(sp(3))-H functionalization of enaminones under metal-free conditions has been developed. An intermolecular Michael addition reaction and an intramolecular condensation were involved in this procedure, which features high regioselectivity; high efficiency, and environmental friendliness. Various polysubstituted pyridines were provided in up to 92% yield for 34 examples.

  DOI：

  10.1021/acs.joc.5b00635

文献信息

• Copper-Catalyzed Formal C–N Bond Cleavage of Aromatic Methylamines: Assembly of Pyridine Derivatives
  作者：Huawen Huang、Xiaochen Ji、Wanqing Wu、Liangbin Huang、Huanfeng Jiang

  DOI：10.1021/jo400261v

  日期：2013.4.19

  copper-catalyzed C–N bond cleavage of aromatic methylamines was developed to construct pyridine derivatives. With neat conditions and facile operation, the fragment-assembling strategy affords a broad range of 2,4,6-trisubstituted pyridines in up to 95% yield from simple and readily available starting materials. Interestingly, when pyridin-2-yl methylamine was employed as the substrate, α-alkylation reaction

  开发了一种有效的铜催化的芳香族甲胺的C–N键裂解，以构建吡啶衍生物。在纯净的条件和简便的操作条件下，片段组装策略可从简单易得的起始原料中获得高达95％的收率的2,4,6-三取代吡啶。有趣的是，当使用吡啶-2-基甲胺作为底物时，酮的α-烷基化反应容易发生，从而得到β-（吡啶-2-基）酮，而不是2,4,6-三取代的吡啶。