2-methyl-3-(9H-xanthen-9-yl)-1H-indole | 62022-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-3-(9H-xanthen-9-yl)-1H-indole
• 英文别名: 2-methyl-3-xanthen-9-yl-indole；2-Methyl-3-xanthen-9-yl-indol；2-Methyl-3-(9-xanthyl)indol
• CAS: 62022-70-2
• 化学式: C₂₂H₁₇NO
• 分子量: 311.383
• InChiKey: AGTDHWKAFVCWCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 2-苯氧基苯甲醛 在 iron(III) chloride hexahydrate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以82%的产率得到2-methyl-3-(9H-xanthen-9-yl)-1H-indole
  参考文献：
  名称：

  Iron-Catalyzed Cascade Arene−Aldehyde Addition/Cyclizations for the Highly Efficient Synthesis of Xanthenes and Its Analogous: Observation of a C−C Bond Cleavage in Indole-Based Triarylmethanes

  摘要：

  An efficient, general, and one-pot procedure for the synthesis of multisubstituted xanthene derivatives through Fe(III)-catalyzed reactions of 2-aryloxybenzaldehydes with electron-rich arenes has been developed. This method offers several advantages such as high selectivities, mild reaction conditions, and easily accessible starting materials. A mechanistic study revealed that a C-C bond cleavage of a triarylmethane intermediate might be involved in the domino process.

  DOI：

  10.1021/jo9012354

文献信息

• 离子液体促进的无溶剂合成3-(9H-氧杂蒽-9-基)-1H-吲哚类化合物的方法
  申请人：河南师范大学

  公开号：CN110041313B

  公开（公告）日：2022-11-18

  本发明公开了一种离子液体促进的无溶剂合成3‑(9H‑氧杂蒽‑9‑基)‑1H‑吲哚类化合物的方法，以吲哚类化合物和占吨醇为反应底物，以甜菜碱类氢键功能化离子液体为催化剂，于50℃反应1‑4h制得目标产物3‑(9H‑氧杂蒽‑9‑基)‑1H‑吲哚类化合物。本发明中离子液体制备简便，且原料具有良好的生物相容性，价廉易得；离子液体用量少，反应条件温和，原子经济性高；此反应无需额外添加溶剂，有效地避免了有毒溶剂的使用；该反应体系对设备无腐蚀性，对反应器无特殊要求，此催化体系的操作及后处理过程简单。因此该方法是工业化合成3‑(9H‑氧杂蒽‑9‑基)‑1H‑吲哚及其衍生物的优选方法。
• Biocompatible ionic liquid [Betaine][H₂PO₄] as a reusable catalyst for the substitution of xanthen-9-ol under solvent-free conditions
  作者：Anlian Zhu、Tong Wang、Wanlu Feng、Jianji Wang、Lingjun Li

  DOI：10.1039/d0ra05374k

  日期：——

  An ionic liquid, namely [Betaine][H2PO4], was found to be an efficient catalyst for the direct substitution reaction of xanthen-9-ol with different nucleophiles under solvent-free conditions. This catalytic system is easy to be operated and the following work-up procedure is simple, with the ionic liquid catalyst reusable for at least five cycles at a high catalytic activity level. In addition, the

  离子液体，即[甜菜碱][H 2 PO 4 ]，被发现是无溶剂条件下xanthen-9-ol与不同亲核试剂直接取代反应的有效催化剂。该催化体系易于操作，后续后处理程序简单，离子液体催化剂可在高催化活性水平下重复使用至少五个循环。此外，离子液体制备简单，原料廉价，生物相容性好。因此，我们的研究提出了一种有趣且可持续的直接替代酒精的方案。
• Indium Tris(dodecyl Sulfonate) [In(DS)₃]–Catalyzed Formation of 3‐(9<i>H</i>‐Xanthen‐9‐yl)‐1<i>H</i>‐indole Derivatives in Water at Room Temperature
  作者：Shun‐Yi Wang、Shun‐Jun Ji

  DOI：10.1080/00397910701578172

  日期：2008.1.1

  Abstract In(DS)3 catalyzes formation of 9H‐xanthen‐9‐ol with indoles at room temperature in water to afford a class of 3‐(9H‐xanthen‐9‐yl)‐1H‐indole derivatives in high yields.

  摘要 In(DS)3 在室温下在水中催化 9H-xanthen-9-ol 与吲哚形成，以高产率得到一类 3-(9H-xanthen-9-yl)-1H-吲哚衍生物。
• Novel Reaction of Indoles and Pyrrole with Pyrillium Catalyzed by Ceric Ammonium Nitrate (CAN)
  作者：Shun-Jun Ji、Shun-Yi Wang

  DOI：10.1055/s-2007-985590

  日期：——

  The reaction of xanthene derivatives with indoles and pyrrole catalyzed by CAN in methanol through S N 1 reaction of -pyrillium with a nucleophilic reagent afforded the corresponding -indole- and pyrrole-substituted xanthene derivatives in high yields, respectively.

  呫吨衍生物与吲哚和吡咯在甲醇中通过-吡咯与亲核试剂的SN 1 反应在甲醇中催化，分别以高产率得到相应的-吲哚-和吡咯-取代的呫吨衍生物。
• Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions
  作者：Weihang Miao、Pingting Ye、Mengjiao Bai、Zhixin Yang、Suyue Duan、Hengpan Duan、Xuequan Wang

  DOI：10.1039/d0ra05217e

  日期：——

  xanthen-9-ol and thioxanthen-9-ol with indoles has been developed, providing an efficient procedure for the synthesis of xanthene/thioxanthene-indole derivatives with good to excellent yields. This protocol offers several advantages, such as short reaction times, green solvent, operational simplicity, easily available catalyst and mild reaction conditions. Moreover, this method showed good tolerance of functional

  开发了一种碘催化的呫吨-9-醇和噻吨-9-醇与吲哚的亲核取代反应，为合成呫吨/噻吨-吲哚衍生物提供了一种有效的方法，且收率良好。该方案具有反应时间短、溶剂绿色、操作简单、催化剂易得和反应条件温和等优点。此外，该方法对官能团和多种底物表现出良好的耐受性。