9-(1-phenylvinyl)-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-(1-phenylvinyl)-9H-carbazole
• 英文别名: 9-(1-Phenylethenyl)carbazole
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: ISAQHQSELLDIQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 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：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  苯乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 氧气 、 lithium tert-butoxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 9-(1-phenylvinyl)-9H-carbazole
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Indoles: Synthesis of N-Vinylindoles

  摘要：

  A general and efficient palladium-catalyzed oxidative cross-coupling reaction of N-tosylhydrazones with indoles providing N-vinylindoles has been developed. The reaction proceeds smoothly with various indoles and N-tosylhydrazones in a stereocontrolled manner, and a wide variety of N-vinylindoles were obtained up to 99% yields for 26 examples.

  DOI：

  10.1021/ol401217h

文献信息

• A General Copper-Catalyzed Coupling of Azoles with Vinyl Bromides
  作者：Qian Liao、Yuxing Wang、Liyun Zhang、Chanjuan Xi

  DOI：10.1021/jo901105r

  日期：2009.8.21

  A copper-catalyzed methodology for the coupling of vinyl bromides with azoles has been developed. This protocol uses a combination of 10 mol % of copper iodide and 20 mol % of ethylenediamine as catalyst. The reaction proceeds with various azoles and vinyl bromides, and the double bond geometry of vinyl bromides is retained under the reaction conditions.

  已经开发了铜催化的乙烯基溴与唑偶联的方法。该方案使用10摩尔％的碘化铜和20摩尔％的乙二胺的组合作为催化剂。反应与各种唑和乙烯基溴一起进行，并且乙烯基溴的双键几何形状在反应条件下得以保留。
• Synthesis of Terminal <i>N</i> ‐Vinylazoles from Aromatic Aldehydes, DMSO, and Azoles Based DMSO as Terminal Carbon Synthon
  作者：Zhiwen Nie、Huifang Lv、Hui Li、Miaodong Su、Tonglin Yang、Weiping Luo、Qiang Liu、Cancheng Guo

  DOI：10.1002/adsc.202100663

  日期：2021.10.5

  A protocol for the synthesis of terminal N-vinylazoles from aromatic aldehydes, DMSO, and azoles has been reported. In this strategy, DMSO was involved in the construction of the C=C bond as a terminal carbon synthon. Both aromatic aldehydes and azoles could be well tolerated and give the corresponding terminal N-vinylazoles in 52–91% yields. Based on preliminary experiments, a plausible mechanism

  已经报道了从芳香醛、DMSO 和唑类合成末端N-乙烯基唑的方案。在该策略中，DMSO 作为末端碳合成子参与了 C=C 键的构建。芳香醛和唑类都具有良好的耐受性，并以 52-91% 的产率得到相应的末端N-乙烯基唑。在初步实验的基础上，提出了一个合理的机制。
• Gold-Catalyzed Carbazolation Reactions of Alkynes
  作者：Sripati Jana、Feifei He、Rene M. Koenigs

  DOI：10.1021/acs.orglett.0c01719

  日期：2020.6.19

  Au(I)-catalyzed reaction of alkynes with carbazoles that enables a one-step synthesis of vinyl carbazoles that are important molecules for applications as photoluminescent materials. This reaction proceeds under mild conditions at room temperature, without the need of external bases, and can be employed to a variety of aromatic and aliphatic alkynes in monohydroamination and poly-hydroamination reactions. We conclude

  在本文中，我们报道了炔烃与咔唑的Au（I）催化反应，该反应能够一步合成乙烯基咔唑，而乙烯基咔唑是用作光致发光材料的重要分子。该反应在室温下在温和条件下进行，不需要外部碱，并且可用于单加氢胺化和多加氢胺化反应中的各种芳族和脂族炔烃。我们以乙烯基咔唑产品的光物理研究作为结束，该产品具有独特的荧光特性。
• Synthesis of <i>N</i>-Vinylcarbazoles via Dehydrogenative Coupling of <i>N</i>-H Carbazoles with Alkenes under Palladium Catalysis
  作者：Daisuke Takeda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol4001697

  日期：2013.3.15

  The synthesis of N-vinylcarbazoles was achieved by the palladium-catalyzed aza-Wacker reaction of N-H carbazoles with styrenes. In this reaction, Markovnikov adducts were exclusively produced. In contrast, the reaction with electron-deficient alkenes such as acrylates and acrylamides gave only anti-Markovnikov adducts.
• Khlebnikov, A.I.; Anfinogenov, V.A.; Moskalev, N.V., Russian Journal of Organic Chemistry, 1993, vol. 29, # 9.2, p. 1573 - 1576
  作者：Khlebnikov, A.I.、Anfinogenov, V.A.、Moskalev, N.V.、Filimonov, V.D.

  DOI：——

  日期：——