N,N-dimethyl-2-((2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)ethynyl)benzenamine | 1258410-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-2-((2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)ethynyl)benzenamine
• CAS: 1258410-58-0
• 化学式: C₂₅H₁₈F₃N
• 分子量: 389.42
• InChiKey: SQPQWUAQGBYYJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-((2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)ethynyl)benzenamine 在 copper dichloride 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到5-chloro-11-methyl-6-(4-(trifluoromethyl)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
• 作为产物：
  描述：

  2-((2-iodophenyl)ethynyl)-N,N-dimethylbenzenamine 、 4-乙炔基-α,α,α-三氟甲苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以68%的产率得到N,N-dimethyl-2-((2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)ethynyl)benzenamine
  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

• Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[<i>a</i>]carbazoles
  作者：Chin-Chau Chen、Shyh-Chyun Yang、Ming-Jung Wu

  DOI：10.1021/jo201795t

  日期：2011.12.16

  Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH2Cl2 gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.