9-(4-butylphenyl)-9H-carbazole | 951659-74-8

• 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-(4-butylphenyl)-9H-carbazole
• 英文别名: 9-(4-Butylphenyl)carbazole；9-(4-butylphenyl)carbazole
• CAS: 951659-74-8
• 化学式: C₂₂H₂₁N
• 分子量: 299.415
• InChiKey: UIERKVPWGJMAJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9-(4-butylphenyl)-9H-carbazole 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 生成 9-(4-butylphenyl)carbazole-3-carbaldehyde N-phenylhydrazone
  参考文献：
  名称：

  9-Phenylcarbazole–Based Hydrazone Twin Compounds as P-Type Organic Semiconductors

  摘要：

  Hole transporting glass-forming low-molar-mass hydrazones containing 9-phenylcarbazole moiety were synthesized and characterized by NMR-, infrared- and mass spectrometries. The thermal, optical and photoelectrical properties of the synthesized compounds are reported. Compounds containing 1,3-benzendithiol linking bridge were isolated as amorphous materials therefore differential scanning calorimetry experiments revealed glass transitions approximately at 60 degrees C. The ionization potentials of the synthesized compounds were measured by electron photoemission technique in air range from 5.23eV to 5.4eV. Hole drift mobilities in the films of the solid solutions of some of the synthesized hydrazones in bisphenol Z polycarbonate measured by the time-of-flight technique exceed 10-5cm2V-1s-1 at high electric fields.

  DOI：

  10.1080/15421406.2011.538605
• 作为产物：
  描述：

  4-正丁基苯胺 、 2,2'-双溴双苯 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以60%的产率得到9-(4-butylphenyl)-9H-carbazole
  参考文献：
  名称：

  空气存在下伯胺与2,2'-二溴代二苯的双N-芳基化反应在铜上高效催化合成咔唑

  摘要：

  据报道，一种有效的铜催化的咔唑衍生物的合成，是通过在空气存在下2,2'-二溴代二苯与胺的双C–N偶联反应进行的。该反应是稳健的，以高收率进行，并且耐受一系列胺，包括中性，富电子，缺电子的芳族胺和脂族胺。

  DOI：

  10.1055/s-0040-1706641

文献信息

• 一种合成咔唑衍生物的方法
  申请人：湖南大学

  公开号：CN113461595A

  公开（公告）日：2021-10-01

  本发明的目的在于提供一种合成咔唑衍生物的方法。其特征在于，以氯化钯作为催化剂，有机锑化合物作为配体，2，2'‑双溴联苯作为亲电试剂，伯胺作为亲核试剂，在甲苯作为溶剂，空气氛围的条件下直接交叉偶联合成咔唑衍生物。该方法具有产率高，选择性高和操作简便等优点。
• Organogelation enables fast organolithium cross-coupling reactions in air
  作者：Paco Visser、Ben L. Feringa

  DOI：10.1039/d3cc00756a

  日期：——

  on palladium-catalysed cross-coupling reactions using organolithium reagents has seen major breakthroughs in the past decade. However, the use of inert conditions, as well as slow addition of the organolithium species, is generally required. Here we describe the Pd-catalysed cross-coupling of C36H74-gelated organolithium reagents with aryl bromides. The reaction proceeds in 5 min at room temperature

  在过去十年中，基于有机锂试剂的钯催化交叉偶联反应的 C-C 键形成取得了重大突破。然而，通常需要使用惰性条件以及缓慢添加有机锂物质。在这里，我们描述了 Pd 催化的 C 36 H 74凝胶化有机锂试剂与芳基溴化物的交叉偶联。反应在室温下进行 5 分钟，同时消除了以前需要的缓慢添加，并严格使用惰性气氛。至关重要的是，有机锂凝胶的使用方便了处理，并极大地提高了过程安全性，不需要任何特殊安全预防措施的克级转化就说明了这一点。
• Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air
  作者：Tran Quang Hung、Tuan Thanh Dang、Peter Langer、Ha Nam Do、Nguyen Minh Quan、Ban Van Phuc、Dinh Van Tinh、Nguyen Quyet Tien、Truong Thi Thanh Nga、Van Tuyen Nguyen

  DOI：10.1055/s-0040-1706641

  日期：2021.4

  An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

  据报道，一种有效的铜催化的咔唑衍生物的合成，是通过在空气存在下2,2'-二溴代二苯与胺的双C–N偶联反应进行的。该反应是稳健的，以高收率进行，并且耐受一系列胺，包括中性，富电子，缺电子的芳族胺和脂族胺。
• 9-Phenylcarbazole–Based Hydrazone Twin Compounds as P-Type Organic Semiconductors
  作者：Ramunas Lygaitis、Juozas Vidas Grazulevicius、Vygintas Jankauskas

  DOI：10.1080/15421406.2011.538605

  日期：2011.3.21

  Hole transporting glass-forming low-molar-mass hydrazones containing 9-phenylcarbazole moiety were synthesized and characterized by NMR-, infrared- and mass spectrometries. The thermal, optical and photoelectrical properties of the synthesized compounds are reported. Compounds containing 1,3-benzendithiol linking bridge were isolated as amorphous materials therefore differential scanning calorimetry experiments revealed glass transitions approximately at 60 degrees C. The ionization potentials of the synthesized compounds were measured by electron photoemission technique in air range from 5.23eV to 5.4eV. Hole drift mobilities in the films of the solid solutions of some of the synthesized hydrazones in bisphenol Z polycarbonate measured by the time-of-flight technique exceed 10-5cm2V-1s-1 at high electric fields.