2-(p-tolyl)-4-phenyl-3-iodoquinoline | 1291079-97-4

• 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-(p-tolyl)-4-phenyl-3-iodoquinoline
• 英文别名: 3-iodo-4-phenyl-2-(p-tolyl)quinoline；3-Iodo-2-(4-methylphenyl)-4-phenylquinoline
• CAS: 1291079-97-4
• 化学式: C₂₂H₁₆IN
• 分子量: 421.28
• InChiKey: WNGROJGGGKGEGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基二苯甲酮 在 吡啶 、 乙基溴化镁 、 碘 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.25h， 生成 2-(p-tolyl)-4-phenyl-3-iodoquinoline
  参考文献：
  名称：

  Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines

  摘要：

  Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I-2) under mild conditions. The cyclization is highly regioselective and the resulting 3-iodoquinolines can be further functionalized by various coupling reactions.

  DOI：

  10.1021/ol2007154

文献信息

• Single-Step Synthesis of 3-Iodoquinolines from 2-Aminophenyl Ketones through a Regioselective (6-<i>endo</i>-<i>dig</i>) Electrophilic Cyclization
  作者：Srinivasarao Yaragorla、Abhishek Pareek、Ravikrishna Dada、Pyare Lal Saini

  DOI：10.1002/ejoc.201700668

  日期：2017.8.24

  A single-step approach to the synthesis of 3-iodoquinolines has been achieved through a regioselective iodocyclization. The synthesis began from readily available materials in an aqueous ethyl acetate medium and was promoted by KOtBu and I2 at room temperature. Various cross-coupling reactions were used to demonstrate the synthetic utility of the products.

  通过区域选择性碘环化已经实现了一步合成3-碘喹啉的方法。合成从乙酸乙酯水溶液介质中容易获得的材料开始，并在室温下通过KO t Bu和I 2促进。各种交叉偶联反应用于证明产物的合成效用。
• Synthesis of 3-Iodoquinolines by Copper-Catalyzed Tandem Annulation from Diaryliodoniums, Nitriles, and 1-Iodoalkynes
  作者：Xuesong Wang、Xingyong Wang、Dayun Huang、Chulong Liu、Xinyan Wang、Yuefei Hu

  DOI：10.1002/adsc.201600081

  日期：2016.7.14

  A novel method for the synthesis of 3‐iodoquinolines was developed by copper‐catalyzed tandem annulation from diaryliodoniums, nitriles, and 1‐iodoalkynes. It is a method that is characterized by the most convenient operation and wide molecular diversity.

  通过铜催化串联从二芳基牙鎓，腈和1-碘代炔烃的环化反应，开发了一种新型的3-碘代喹啉合成方法。该方法以最方便的操作和广泛的分子多样性为特征。