4-(3-aminobenzyl)-3-phenyl-9-tosyl-9H-carbazole | 1577228-87-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-(3-aminobenzyl)-3-phenyl-9-tosyl-9H-carbazole
• 英文别名: 3-[[9-(4-Methylphenyl)sulfonyl-3-phenylcarbazol-4-yl]methyl]aniline；3-[[9-(4-methylphenyl)sulfonyl-3-phenylcarbazol-4-yl]methyl]aniline
• CAS: 1577228-87-5
• 化学式: C₃₂H₂₆N₂O₂S
• 分子量: 502.637
• InChiKey: QFURBXAIRFOCDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  73.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-aminobenzyl)-3-phenyl-9-tosyl-9H-carbazole 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到
  参考文献：
  名称：

  Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal Alkynes

  摘要：

  The Pd/Cu-cocatalyzed one-pot reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and terminal alkynes afforded carbazoles highly efficiently via sequential carbon carbon coupling, isomerization, cyclization, and aromatization forming a benzene ring. Both Pd and Cu are responsible for the coupling step, while K2CO3 was observed to be critical for the subsequent cyclization.

  DOI：

  10.1021/ol500119r
• 作为产物：
  描述：

  3-iodo-2-(3-phenylallyl)-1-tosyl-1H-indole 、 3-氨基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以77%的产率得到4-(3-aminobenzyl)-3-phenyl-9-tosyl-9H-carbazole
  参考文献：
  名称：

  Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal Alkynes

  摘要：

  The Pd/Cu-cocatalyzed one-pot reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and terminal alkynes afforded carbazoles highly efficiently via sequential carbon carbon coupling, isomerization, cyclization, and aromatization forming a benzene ring. Both Pd and Cu are responsible for the coupling step, while K2CO3 was observed to be critical for the subsequent cyclization.

  DOI：

  10.1021/ol500119r

文献信息

• Efficient Carbazole Synthesis via Pd/Cu-Cocatalyzed Cross-Coupling/Isomerization of 2-Allyl-3-iodoindoles and Terminal Alkynes
  作者：Can Zhu、Shengming Ma

  DOI：10.1021/ol500119r

  日期：2014.3.21

  The Pd/Cu-cocatalyzed one-pot reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and terminal alkynes afforded carbazoles highly efficiently via sequential carbon carbon coupling, isomerization, cyclization, and aromatization forming a benzene ring. Both Pd and Cu are responsible for the coupling step, while K2CO3 was observed to be critical for the subsequent cyclization.