3-(1-(2-methylphenyl)-2-phenylselenoethyl)-1H-indole | 1000682-74-5

• 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: 3-(1-(2-methylphenyl)-2-phenylselenoethyl)-1H-indole
• 英文别名: 3-[1-(2-methylphenyl)-2-phenylselanylethyl]-1H-indole
• CAS: 1000682-74-5
• 化学式: C₂₃H₂₁NSe
• 分子量: 390.386
• InChiKey: DLYRHGKJEPTRAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吲哚 、 N-(苯硒基)邻苯二甲酰亚胺 、 2-甲基苯乙烯 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以69%的产率得到3-(1-(2-methylphenyl)-2-phenylselenoethyl)-1H-indole
  参考文献：
  名称：

  Novel Brønsted Acid Catalyzed Three-Component Alkylations of Indoles with N-Phenylselenophthalimide and Styrenes

  摘要：

  Novel and efficient Bronsted acid (p-TsOH) catalyzed inter- and intramolecular Friedel-Crafts alkylations have been developed to synthesize selenated three-component coupling and selenation-cyclization indole derivatives. Chemical removal of the phenylseleno moiety was investigated, and the reaction mechanisms were discussed.

  DOI：

  10.1021/ol7024795

文献信息

• Blue LED light‐promoted CuCl₂‐catalyzed three component reaction of styrenes, indoles, and diselenides
  作者：Xianjie Yin、Helin Wang、Lei Shen、Qingle Zeng

  DOI：10.1002/aoc.7231

  日期：2023.10

  A three-component reaction of olefins, indoles, and diaryl diselenides catalyzed by copper chloride under irradiation of blue LED light is disclosed. Various diaryl diselenides including diheteroaryl diselenides are suitable for this bifunctionalization of olefins. This protocol provides 26 examples of β-(hetero)arylselenyl indoles in 60%–87% yields. The proposed mechanism involves activation of diaryl

  公开了在蓝色LED光照射下由氯化铜催化的烯烃、吲哚和二芳基二硒化物的三组分反应。包括二杂芳基二硒化物在内的各种二芳基二硒化物适合于烯烃的这种双官能化。该方案提供了 26 个 β-(杂)芳基硒基吲哚的例子，产率为 60%–87%。所提出的机制包括通过与氯化铜配位活化二芳基二硒化物，通过活化二芳基二硒化物的杂解生成芳基硒阳离子，将芳基硒阳离子亲电加成到苯乙烯上，然后在NH-吲哚的3位上进行弗里德尔-克来福特型烷基化。
• Novel Brønsted Acid Catalyzed Three-Component Alkylations of Indoles with <i>N</i>-Phenylselenophthalimide and Styrenes
  作者：Xiaodan Zhao、Zhengkun Yu、Tongyu Xu、Ping Wu、Haifeng Yu

  DOI：10.1021/ol7024795

  日期：2007.12.1

  Novel and efficient Bronsted acid (p-TsOH) catalyzed inter- and intramolecular Friedel-Crafts alkylations have been developed to synthesize selenated three-component coupling and selenation-cyclization indole derivatives. Chemical removal of the phenylseleno moiety was investigated, and the reaction mechanisms were discussed.