9-(1-(4-chlorophenyl)vinyl)-9H-carbazole | 1426066-90-1

• 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-(4-chlorophenyl)vinyl)-9H-carbazole
• 英文别名: 9-[1-(4-Chlorophenyl)ethenyl]carbazole；9-[1-(4-chlorophenyl)ethenyl]carbazole
• CAS: 1426066-90-1
• 化学式: C₂₀H₁₄ClN
• 分子量: 303.791
• InChiKey: ZSERHTHMESOZQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 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：

  4-氯苯乙烯 、 咔唑 在 palladium diacetate 、 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到9-(1-(4-chlorophenyl)vinyl)-9H-carbazole
  参考文献：
  名称：

  Synthesis of N-Vinylcarbazoles via Dehydrogenative Coupling of N-H Carbazoles with Alkenes under Palladium Catalysis

  摘要：

  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.

  DOI：

  10.1021/ol4001697

文献信息

• 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。
• Catalytic hydroaminations of alkynes: a facile protocol to vinyl-carbazole derivatives <i>via</i> a frustrated Lewis pair mechanism
  作者：Yunbo Zhao、Lvnan Jin、Jing Guo、Douglas W. Stephan

  DOI：10.1039/d1cc07171h

  日期：——

  N-Vinylcarbazoles are important skeletons for photoluminescent materials. Herein, a transition metal-free, B(C6F5)3 mediated carbazolation reaction of alkynes is reported, providing 24 variants of N-vinylcarbazole derivatives. These N-vinylcarbazole products were obtained in good to excellent yields (up to 99%) under mild reaction conditions and could be performed on a gram scale.

  N-乙烯基咔唑是光致发光材料的重要骨架。本文报道了一种不含过渡金属的 B(C 6 F 5 ) 3介导的炔烃咔唑化反应，提供了 24 种N-乙烯基咔唑衍生物的变体。这些N-乙烯基咔唑产物在温和的反应条件下以良好至优异的产率（高达 99%）获得，并且可以以克级规模进行。