phenyl(2-phenyl-3-(phenylselanyl)-1H-indol-1-yl)methanone | 1612876-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: phenyl(2-phenyl-3-(phenylselanyl)-1H-indol-1-yl)methanone
• CAS: 1612876-03-5
• 化学式: C₂₇H₁₉NOSe
• 分子量: 452.414
• InChiKey: OQRYHZMKAKRBRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-苯基乙炔基胺 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z)-2-phenyl-4-(phenyl(phenylselanyl)methylene)-4H-benzo[d][1,3]oxazine 、 phenyl(2-phenyl-3-(phenylselanyl)-1H-indol-1-yl)methanone
  参考文献：
  名称：

  氯化铁/三有机二硒化物促进邻炔基丙二胺的区域和立体选择性环化：( Z）-4-（硫属元素）亚甲基苯并恶嗪的合成

  摘要：

  AbstractIntramolecular 6‐exo‐dig cyclization of ortho‐alkynylanilides has been employed in a regio‐ and stereoselective synthesis of (Z)‐4‐(chalcogen)methylenebenzoxazines. Several reaction parameters were screened for the efficient cyclization of ortho‐alkynylanilides. Among them, the reaction of ortho‐alkynylanilides (0.25 mmol) with iron(III) chloride (3.0 equiv.) and diorganyl diselenides (0.75 equiv.) in dichloromethane as solvent gave the products in acceptable to good yields. The resulting products were then subjected to a nitrogen–oxygen exchange reaction with ammonium acetate to furnish quinazoline derivatives. The one‐pot version of this cyclization, starting directly from 2‐alkynylanilines, avoiding the previous preparation of ortho‐alkynylanilides was also briefly studied.magnified image

  DOI：

  10.1002/adsc.201300925

文献信息

• Direct Electrooxidative Selenylamination of Alkynes: Access to 3‐Selenylindoles
  作者：Balati Hasimujiang、Yong Zeng、Shifeng Zou、Kaihui Zhong、Lebin Su、Xinwei Hu、Zhixiong Ruan

  DOI：10.1002/ijch.202300088

  日期：2024.1

  A novel metal‐ and oxidant‐free electrooxidative selenylamination of o‐aminophenacetylenes with diselenides for achieving 3‐selenylindoles has been developed with moderate to excellent yield. The reaction proceeded smoothly with a broad substrate scope and highly functional group tolerance. The synthetic practicality of this innovative approach was demonstrated by its easy scalability. Moreover, mechanistic studies revealed that an in‐situ generated selenium cation might be the key intermediate for the electrochemical selenocyclization process.

  摘要 研究人员开发了一种新型的无金属和氧化剂的邻氨基苯乙炔与二硒化物的电氧化硒化反应，以获得 3-硒基吲哚，该反应具有中等到极好的收率。反应进行顺利，底物范围广，官能团耐受性高。这种创新方法的易扩展性证明了其合成的实用性。此外，机理研究表明，原位生成的硒阳离子可能是电化学硒环化过程的关键中间体。