N,N-dimethyl-2-((2-(pent-1-ynyl)phenyl)ethynyl)benzenamine | 1258410-43-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-2-((2-(pent-1-ynyl)phenyl)ethynyl)benzenamine
• 英文别名: N,N-dimethyl-2-[(2-(pent-1-ynyl)phenyl)ethynyl]aniline；N,N-dimethyl 2-[2-(2-ethynylphenyl)-ethynyl]aniline；N,N-dimethyl-2-[2-(2-pent-1-ynylphenyl)ethynyl]aniline
• CAS: 1258410-43-3
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: BOZRRXLPMUOHIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-((2-(pent-1-ynyl)phenyl)ethynyl)benzenamine 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到5-iodo-11-methyl-6-propyl-11H-benzo[a]carbazole
  参考文献：
  名称：

  Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles

  摘要：

  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.

  DOI：

  10.1021/jo201795t
• 作为产物：
  描述：

  1-戊炔 、 2-((2-iodophenyl)ethynyl)-N,N-dimethylbenzenamine 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75%的产率得到N,N-dimethyl-2-((2-(pent-1-ynyl)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

• 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.
• 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.