9-ethyl-3-isocyanocarbazole | 602262-80-6

• 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-ethyl-3-isocyanocarbazole
• CAS: 602262-80-6
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: BRPASVPFNMEUQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  9.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-ethyl-3-isocyanocarbazole 、 Au(C6F5)*thf 以 二氯甲烷 为溶剂， 以65%的产率得到[Au(C6F5)(9-ethyl-3-isocyanocarbazole)]
  参考文献：
  名称：

  Synthesis and Characterization of Gold(I) Complexes with 9‐(4‐Isocyanophenyl)carbazole or 9‐Ethyl‐3‐isocyanocarbazole Ligands

  摘要：

  AbstractThe carbazole derivatives 9‐(4‐isocyanophenyl)carbazole, 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole, and 9‐ethyl‐3‐isocyanocarbazole were prepared and used to synthesize [AuX(CN‐carbazole)] (X = Cl, C6F5, C6F4‐OEt‐p) gold complexes. The X‐ray structures of [Au(C6F4‐OEt‐p){9‐(4‐isocyanophenyl)carbazole}] and [Au(C6F5)(9‐ethyl‐3‐isocyanocarbazole)], and the luminescent properties of the ligands and the complexes in the solid state, in solution at room temperature, and in frozen solution of chloroform at 77 K were determined. All the gold complexes show a redshift in the emissions relative to that of the free ligand. The presence of electron‐withdrawing substituents in 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole quenches the luminescence, but with the introduction of a gold atom some luminescence is recovered.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejic.200900692
• 作为产物：
  描述：

  N-(9-ethyl-9H-carbazol-3-yl)formamide 在 三光气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到9-ethyl-3-isocyanocarbazole
  参考文献：
  名称：

  Synthesis and Characterization of Gold(I) Complexes with 9‐(4‐Isocyanophenyl)carbazole or 9‐Ethyl‐3‐isocyanocarbazole Ligands

  摘要：

  AbstractThe carbazole derivatives 9‐(4‐isocyanophenyl)carbazole, 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole, and 9‐ethyl‐3‐isocyanocarbazole were prepared and used to synthesize [AuX(CN‐carbazole)] (X = Cl, C6F5, C6F4‐OEt‐p) gold complexes. The X‐ray structures of [Au(C6F4‐OEt‐p){9‐(4‐isocyanophenyl)carbazole}] and [Au(C6F5)(9‐ethyl‐3‐isocyanocarbazole)], and the luminescent properties of the ligands and the complexes in the solid state, in solution at room temperature, and in frozen solution of chloroform at 77 K were determined. All the gold complexes show a redshift in the emissions relative to that of the free ligand. The presence of electron‐withdrawing substituents in 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole quenches the luminescence, but with the introduction of a gold atom some luminescence is recovered.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejic.200900692

文献信息

• Radical Cyanotrifluoromethylation of Isocyanides: Step-Economical Access to CF₃-Containing Nitriles, Amines, and Imines
  作者：Shuang Chen、Da-Fu Feng、Deng-Yuan Li、Pei-Nian Liu

  DOI：10.1021/acs.orglett.8b02328

  日期：2018.9.7

  A novel copper-catalyzed radical cyanotrifluoromethylation has been achieved through a multicomponent reaction of isocyanides, Togni’s reagent, and trimethylsilyl cyanides, affording trifluoroacetimidoyl nitriles in good yields. This reaction demonstrates a unique feature of merging two valuable functional groups—trifluoromethyl (CF3) and cyan (CN)—onto the same C atom. The transformation proceeds

  通过异氰酸酯，Togni试剂和三甲基甲硅烷基氰化物的多组分反应，已实现了新型的铜催化的自由基氰基三氟甲基化，可提供高收率的三氟乙酰亚胺基腈。该反应证明了将两个有价值的官能团-三氟甲基（CF 3）和氰基（CN）-合并到同一C原子上的独特功能。转化过程是通过将CF 3自由基最初加到异氰酸酯中以及随后的分子间C-CN形成而进行的。该产品可以成功转化为一系列含CF 3的胺和亚胺，可用于合成有价值的药物和农用化学品。
• Synthesis and Characterization of Gold(I) Complexes with 9‐(4‐Isocyanophenyl)carbazole or 9‐Ethyl‐3‐isocyanocarbazole Ligands
  作者：Rut Benavente、Pablo Espinet、Sergio Lentijo、Jose M. Martín‐Álvarez、Jesús A. Miguel、M. Paz Rodríguez‐Medina

  DOI：10.1002/ejic.200900692

  日期：2009.12

  AbstractThe carbazole derivatives 9‐(4‐isocyanophenyl)carbazole, 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole, and 9‐ethyl‐3‐isocyanocarbazole were prepared and used to synthesize [AuX(CN‐carbazole)] (X = Cl, C6F5, C6F4‐OEt‐p) gold complexes. The X‐ray structures of [Au(C6F4‐OEt‐p)9‐(4‐isocyanophenyl)carbazole}] and [Au(C6F5)(9‐ethyl‐3‐isocyanocarbazole)], and the luminescent properties of the ligands and the complexes in the solid state, in solution at room temperature, and in frozen solution of chloroform at 77 K were determined. All the gold complexes show a redshift in the emissions relative to that of the free ligand. The presence of electron‐withdrawing substituents in 3,6‐dibromo‐9‐(4‐isocyanophenyl)carbazole quenches the luminescence, but with the introduction of a gold atom some luminescence is recovered.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)