4-(p-tolyl)-2H-chromene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(p-tolyl)-2H-chromene
• 英文别名: 4-(4-methylphenyl)-2H-chromene
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: BVISVEAMGPLONH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 在 1,1'-双(二苯基膦)二茂铁 、 双(乙腈)氯化钯(II) 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.08h， 生成 4-(p-tolyl)-2H-chromene
  参考文献：
  名称：

  Rapid synthesis of 4-arylchromenes from ortho-substituted alkynols: A versatile access to restricted isocombretastatin A-4 analogues as antitumor agents

  摘要：

  Potent anticancer 4-arylchromene agents 6, as restricted isoCA-4 analogues, were prepared with excellent yields by a rapid and versatile synthetic pathway. First, in the presence of PTSA in EtOH, a variety of arylalkynols 9 were transformed into substituted 4-chromanones 10 in a one pot procedure which include regioselective arylalkynols hydration, alcohol etherification, MOM-cleavage, and cyclization. Further palladium coupling reactions, using aryl halides and N-tosylhydrazones 11 gave access to a small library of functionalized 4-arylchromenes 6 with good yields. From this series of 4-arylchromenes, we have identified compound 6s which inhibit tubulin assembly at a micromolar level and demonstrate a remarkable nanomolar level of cytotoxicity against four human cancer cell lines. Docking studies showed that isoCA-4 and its restricted chromene analogue 6s adopt a similar positioning in the colchicine binding-site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.024

文献信息

• Synthesis of Neoflavenes by a Palladium-Catalyzed Cross-Coupling Reaction of 4-Trifluoromethylsulfonyloxy-2<i>H</i>-Chromenes with Arylboronic Acids
  作者：Tetsuya Eguchi、Yukio Hoshino、Akimi Ayame

  DOI：10.1246/bcsj.75.581

  日期：2002.3

  Under anhydrous conditions, 4-phenyl-2H-chromenes were obtained in excellent yields by a cross-coupling reaction of 4-trifluoromethylsulfonyloxy-2H-chromenes with arylboronic acids, except for o-methoxyphenylboronic acid, in the presence of K2CO3 and several palladium catalysts. Although copper(I) iodide, used as a co-catalyst, showed no effect on this reaction, it was confirmed to act in the case

  在无水条件下，通过 4-三氟甲基磺酰氧基-2H-色烯与芳基硼酸（邻甲氧基苯基硼酸除外）在 K2CO3 和几种钯催化剂存在下的交叉偶联反应，以优异的收率获得了 4-苯基-2H-色烯. 尽管用作助催化剂的碘化铜 (I) 对该反应没有影响，但证实在 4-三氟甲基磺酰氧基-2H-色烯与三丁基苯基锡的偶联反应中起作用，而不是苯硼酸，在[Pd(PPh3)4] 的存在。