5-chloro-11-methyl-6-phenyl-11H-benzo[a]carbazole | 1258410-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-chloro-11-methyl-6-phenyl-11H-benzo[a]carbazole
• 英文别名: 5-Chloro-11-methyl-6-phenylbenzo[a]carbazole；5-chloro-11-methyl-6-phenylbenzo[a]carbazole
• CAS: 1258410-76-2
• 化学式: C₂₃H₁₆ClN
• 分子量: 341.84
• InChiKey: AMAIUIIBPYWYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)aniline 在 copper dichloride 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到5-chloro-11-methyl-6-phenyl-11H-benzo[a]carbazole
  参考文献：
  名称：

  Synthetic Development and Mechanistic Study on Pd(II)-Catalyzed Cyclization of Enediynes to Benzo[a]carbazoles

  摘要：

  Treatment of N,N-dimethyl 2[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol he of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.

  DOI：

  10.1021/ol1024458

文献信息

• Synthetic Development and Mechanistic Study on Pd(II)-Catalyzed Cyclization of Enediynes to Benzo[<i>a</i>]carbazoles
  作者：Chin-Chau Chen、Lin-Yu Chin、Shyh-Chyun Yang、Ming-Jung Wu

  DOI：10.1021/ol1024458

  日期：2010.12.17

  Treatment of N,N-dimethyl 2[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol he of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.