4-phenylbenzo[c][2,7]naphthyridine | 127056-10-4

• 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: 4-phenylbenzo[c][2,7]naphthyridine
• 英文别名: Benzo[c][2,7]naphthyridine, 4-phenyl-
• CAS: 127056-10-4
• 化学式: C₁₈H₁₂N₂
• 分子量: 256.307
• InChiKey: NWDWDVMKHQSOJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 4-phenylbenzo[c][2,7]naphthyridine-5-carboxylate 在 polyphosphoric acid 作用下， 反应 5.0h， 以22%的产率得到4-phenylbenzo[c][2,7]naphthyridine
  参考文献：
  名称：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin

  摘要：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin starting from readily available 4-bromobenzo[c][2,7]naphthyridine (10) comprises a high-yield Minisci-type homolytic methoxycarbonylation at C-5, followed by introduction of the ring A scaffold via Suzuki cross-coupling reaction, and a trifluoromethanesulfonic acid-aided Friedel-Crafts-type intramolecular acylation. This protocol allows for the introduction of various electron-rich carbocyclic and heterocyclic ring A substitutes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.085

文献信息

• Reactivity of 4-chlorobenzo[<i>c</i>][2,7]naphthyridines towards Pd(0) catalyzed coupling reactions and nucleophilic substitutions. aroylation by nucleophilic substitution with analogues of acyl anions
  作者：G. Duvey、F. Nivoliers、P. Rocca、A. Godard、F. Marsais、G. Quéguiner

  DOI：10.1002/jhet.5570380505

  日期：2001.9

  Various 4-substituted benzo[c][2,7]naphthyridines were prepared from the corresponding 4-chloro derivative by Pd(0) coupling reaction or nucleophilic substitution. More particularly, 4-aroyl-benzo[e][2,7]naph-thyridines were synthesized by aroylation with arenecarbaldehydes in the presence of 1,3-dimethylimida-zolium iodide.

  通过Pd（0）偶联反应或亲核取代反应，由相应的4-氯衍生物制备了各种4-取代的苯并[ c ] [2,7]萘啶。更特别地，在1，3-二甲基咪唑-碘化锆存在下，通过与芳烃甲醛的芳基化反应，合成了4-芳酰基-苯并[e] [2，7]萘-吡啶。