9-[(E)-(4-nitrophenyl)vinyl-9H-carbazole

• 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: 9-[(E)-(4-nitrophenyl)vinyl-9H-carbazole
• 英文别名: (E)-9-(4-nitrostyryl)-9H-carbazole；9-[(e)-(4-Nitrophenyl)vinyl]-9h-carbazole；9-[(E)-2-(4-nitrophenyl)ethenyl]carbazole
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: UXSCLGBLTWQQBT-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-乙烯基咔唑 在 tris(dibenzylideneacetone)dipalladium (0) 、 Ru(CO)H(Cl)(tri(cyclohexyl)phosphine)₃ 乙烯基硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 44.0h， 生成 9-[(E)-(4-nitrophenyl)vinyl-9H-carbazole
  参考文献：
  名称：

  Highly stereoselective synthesis of para-substituted (E)-N-styrylcarbazoles via sequential silylative coupling–Hiyama coupling reaction

  摘要：

  A series of new para-substituted (E)-(N)-styrylcarbazoles, i.e., eight (E)-9-[2-(aryl)ethenyl]-9H-carbazoles (5-12) and 1,4-bis[(E)-2-(9H-carbazol-9-yl)vinyl]benzene (13), have been synthesized in high yield and stereoselectively by a sequential silylative coupling-Hiyama coupling reaction, i.e., coupling of commercially available 9-vinylcarbazole with vinyltriethoxysilane or divinyltetrame-thyldisiloxane in the presence of [RuHCl(CO)(PCy3)(2)] (1), followed by Pd (11) catalyzed cross-coupling with para- substituted iodobenzenes. The tandem procedure has facilitated the synthesis of 13. X-ray structures of the intermediate silylvinylcarbazole (4), as well as products 12 and 13 have been obtained. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.065

文献信息

• Highly stereoselective synthesis of para-substituted (E)-N-styrylcarbazoles via sequential silylative coupling–Hiyama coupling reaction
  作者：Wiesław Prukała、Bogdan Marciniec、Mariusz Majchrzak、Maciej Kubicki

  DOI：10.1016/j.tet.2006.11.065

  日期：2007.1

  A series of new para-substituted (E)-(N)-styrylcarbazoles, i.e., eight (E)-9-[2-(aryl)ethenyl]-9H-carbazoles (5-12) and 1,4-bis[(E)-2-(9H-carbazol-9-yl)vinyl]benzene (13), have been synthesized in high yield and stereoselectively by a sequential silylative coupling-Hiyama coupling reaction, i.e., coupling of commercially available 9-vinylcarbazole with vinyltriethoxysilane or divinyltetrame-thyldisiloxane in the presence of [RuHCl(CO)(PCy3)(2)] (1), followed by Pd (11) catalyzed cross-coupling with para- substituted iodobenzenes. The tandem procedure has facilitated the synthesis of 13. X-ray structures of the intermediate silylvinylcarbazole (4), as well as products 12 and 13 have been obtained. (c) 2006 Elsevier Ltd. All rights reserved.