2-(6-methoxy-1H-indol-3-yl)quinoline-3-carbonitrile | 1366500-70-0

• 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-(6-methoxy-1H-indol-3-yl)quinoline-3-carbonitrile
• CAS: 1366500-70-0
• 化学式: C₁₉H₁₃N₃O
• 分子量: 299.332
• InChiKey: YDWHKZUXXIWDPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 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：
  61.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-甲氧基吲哚 、 2-氯喹啉-3-甲腈 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.0h， 以72%的产率得到2-(6-methoxy-1H-indol-3-yl)quinoline-3-carbonitrile
  参考文献：
  名称：

  C–C bond formation at C-2 of a quinoline ring: Synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors

  摘要：

  A number of 2-(1H-indol-3-yl) quinoline-3-carbonitrile derivatives were synthesized via AlCl3-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC50 similar to 0.89 mu M) is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.027

文献信息

• Direct Access to Nitrogen Bi-heteroarenes via Iridium-Catalyzed Hydrogen-Evolution Cross-Coupling Reaction
  作者：Chunlian Chen、Xiuwen Chen、He Zhao、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acs.orglett.7b01349

  日期：2017.7.7

  Through cooperative actions of iridium catalyst and NaOTf additive we report a new direct access to nitrogen bi-heteroarenes via hydrogen-evolution cross-coupling of the β-site of indoles/pyrrole with the α-site of N-heteroarenes. The reaction proceeds in an atom- and redox-economic fashion together with the merits of an easily available catalyst system, broad substrate scope, excellent functional

  通过铱催化剂和NaOTf添加剂的协同作用，我们报道了通过吲哚/吡咯的β-位与N-杂芳烃的α-位的氢演化交叉偶联而直接获得双氮杂氮的新途径。该反应以原子经济和氧化还原经济的方式进行，同时具有易于获得的催化剂体系，广泛的底物范围，优异的功能耐受性和无需外部氧化剂的优点，提供了创建π共轭体系的实用方法。