N,5-dimethyl-2-phenyl-3-(phenylselenyl)-1H-indole | 1448145-42-3

• 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: N,5-dimethyl-2-phenyl-3-(phenylselenyl)-1H-indole
• 英文别名: 1,5-Dimethyl-2-phenyl-3-phenylselanylindole；1,5-dimethyl-2-phenyl-3-phenylselanylindole
• CAS: 1448145-42-3
• 化学式: C₂₂H₁₉NSe
• 分子量: 376.36
• InChiKey: HXKBRMPJKYXRFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N,5-dimethyl-2-phenyl-3-(phenylselenyl)-1H-indole 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以60%的产率得到1,5-dimethyl-2-phenyl-1H-indole
  参考文献：
  名称：

  Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indoles

  摘要：

  In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.

  DOI：

  10.1055/s-0033-1338427
• 作为产物：
  描述：

  N,N-dimethyl-4-methyl-2-(phenylethynyl)aniline 、 二苯基二硒醚 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 以75%的产率得到N,5-dimethyl-2-phenyl-3-(phenylselenyl)-1H-indole
  参考文献：
  名称：

  Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indoles

  摘要：

  In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.

  DOI：

  10.1055/s-0033-1338427

文献信息

• Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indoles
  作者：Gilson Zeni、Adriane Sperança、Benhur Godoi、Paulo Menezes

  DOI：10.1055/s-0033-1338427

  日期：——

  In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.