5-methoxy-3-(2-phenyl-4H-chromen-4-yl)-1H-indole | 1575402-41-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5-methoxy-3-(2-phenyl-4H-chromen-4-yl)-1H-indole
• 英文别名: 4-(5-methoxyindol-3-yl)-2-phenyl-4H-chromene
• CAS: 1575402-41-3
• 化学式: C₂₄H₁₉NO₂
• 分子量: 353.42
• InChiKey: NFEHGTAIKWNSDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 2-羟基查耳酮 在 油酸 作用下， 以 水 为溶剂， 反应 4.0h， 以68%的产率得到5-methoxy-3-(2-phenyl-4H-chromen-4-yl)-1H-indole
  参考文献：
  名称：

  扩展了基于色烯和嘧啶基支架的多样性导向合成中油酸催化的范围†

  摘要：

  发现容易获得的无毒，可生物降解的油酸可以在水介质中以高收率催化4 H-色烯衍生物的合成。还开发了一种通过假三组分，三组分和四组分反应用于油酸催化的嘧啶融合杂环合成的简便多米诺一锅方案。所有产品均以良好至极好的收率获得。油酸催化进一步扩展到基于姜黄素的生物活性分子的合成。

  DOI：

  10.1039/c6ra02507b

文献信息

• A bio-inspired synthesis of hybrid flavonoids from 2-hydroxychalcone driven by visible light
  作者：Yu-Qi Gao、Yi Hou、Liming Zhu、Guzhou Chen、Dongyang Xu、Sheng-Yong Zhang、Yupeng He、Weiqing Xie

  DOI：10.1039/c9ra07198a

  日期：——

  deliver structurally diverse hybrid flavonoids in good to excellent yields in the presence of a catalytic Brønsted acid. Moreover, moderate enantioselectivities could be obtained using a catalytic chiral phosphoric acid via counter anion directed addition. Based on mechanistic studies, the reaction is proposed to proceed via tandem double-bond isomerization/dehydrated cyclization of 2-hydroxychalcone

  描述了一种由 2-羟基查耳酮合成的杂合类黄酮的仿生合成。在 24 W CFL 的照射下，2-羟基查耳酮与各种亲核试剂反应，在催化布朗斯台德酸存在下以良好至优异的产率提供结构多样的杂化黄酮类化合物。此外，使用催化手性磷酸通过反阴离子定向加成可以获得中等的对映选择性。基于机理研究，该反应被提议通过2-羟基查耳酮的串联双键异构化/脱水环化形成瞬时黄鎓阳离子，该阳离子被亲核试剂原位捕获以提供杂化黄酮类化合物。
• A facile synthesis of 2-aryl-4-(indol-3-yl)-4H-chromenes using amberlyst-15 as an efficient recyclable heterogeneous catalyst
  作者：Chayan Guha、Nayim Sepay、Asok K. Mallik

  DOI：10.1007/s00706-014-1401-8

  日期：2015.8

  Starting from 2-hydroxychalcones and indoles, a facile synthesis of 2-aryl-4-(indol-3-yl)-4H-chromenes has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition, cyclization, and dehydration.
• 2-Methylindole as an Indicative Nucleophile for Developing a Three-Component Reaction of Aldehyde with Two Different Nucleophiles
  作者：Dan Jiang、Xiaojuan Pan、Minghao Li、Yanlong Gu

  DOI：10.1021/co500010x

  日期：2014.6.9

  2-Methylindole was used as an indicative nucleophile for rapid screening of MCRs of aldehydes with two different nucleophiles. By removal of some samples that have characteristic color associated with the generation of di(indolyOmethane derivatives the difficulties encountered in the product analysis were alleviated significantly.