N-(2-bromophenyl)quinolin-3-amine | 848086-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(2-bromophenyl)quinolin-3-amine
• 英文别名: 3-(2-bromophenylamino)quinoline；3-(2-Bromophenylamino) quinoline
• CAS: 848086-11-3
• 化学式: C₁₅H₁₁BrN₂
• 分子量: 299.17
• InChiKey: NBGOVSMYVJIBRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  425.7±30.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-bromophenyl)quinolin-3-amine 在 bis-triphenylphosphine-palladium(II) chloride sodium acetate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 5,7-dimethyl-7H-indolo[2,3-c]quinolin-5-ium iodide
  参考文献：
  名称：

  Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

  摘要：

  7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting front 4-chloroquinotine and [2-[(2-2dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2.3-c]quinotine yielded 5-methyl-5H-indolo[2,3c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.073
• 作为产物：
  描述：

  3-溴喹啉 、 2-溴苯胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以83%的产率得到N-(2-bromophenyl)quinolin-3-amine
  参考文献：
  名称：

  Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine

  摘要：

  7H-Indolo[2,3-c]quinoline has been synthesized in two steps via a new approach starting from commercially available 3-bromoquinoline and 2-bromoaniline. The new methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald/Hartwig amination followed by an intramolecular Heck-type reaction. Alternatively, the same skeleton has also been prepared via the combination of a Suzuki arylation with an intramolecular nitrene insertion starting front 4-chloroquinotine and [2-[(2-2dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of 7H-indolo[2.3-c]quinotine yielded 5-methyl-5H-indolo[2,3c]quinoline (Isoneocryptolepine) which is an interesting new lead compound in the search for new antiplasmodial drugs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.073

文献信息

• [EN] CYCLAMINEPHENYLAMINOQUINOLINES AS FUNGICIDES<br/>[FR] CYCLAMINEPHÉNYLAMINOQUINOLÉINES UTILES EN TANT QUE FONGICIDES
  申请人：BAYER AG

  公开号：WO2021209490A1

  公开（公告）日：2021-10-21

  The present disclosure relates to fungicidal active compounds, more specifically to cyclaminephenylaminoquinolines of formula (I), intermediates for their preparation and use thereof as fungicidal active compound, particularly in the form of fungicide compositions. The present disclosure also relates to methods for the control of phytopathogenic fungi of plants using these compounds or compositions comprising thereof.

  本公开涉及杀真菌活性化合物，更具体地涉及公式（I）的环氨基苯胺喹啉类化合物，以及其制备的中间体和作为杀真菌活性化合合物的用途，特别是以杀菌剂组合物的形式。本公开还涉及使用这些化合物或包含其的组合物控制植物病原真菌的方法。
• [EN] HETEROARYLPHENYLAMINOQUINOLINES AND ANALOGUES<br/>[FR] HÉTÉROARYLPHÉNYLAMINOQUINOLÉINES ET ANALOGUES
  申请人：BAYER AG

  公开号：WO2018197692A1

  公开（公告）日：2018-11-01

  The present disclosure relates to fungicidal active compounds, more specifically to heteroarylphenylaminoquinolines and analogues thereof, processes and, intermediates for their preparation and use thereof as fungicidal active compound, particularly in the form of fungicide compositions. The present disclosure also relates to methods for the control of phytopathogenic fungi of plants using these compounds or compositions comprising thereof.

  本公开涉及杀真菌活性化合物，更具体地涉及杂环芳基氨基喹啉及其类似物，以及其制备的过程、中间体和作为杀真菌活性化合物的使用，特别是以杀菌剂组合物的形式。本公开还涉及使用这些化合物或包含它们的组合物来控制植物的植物病原真菌的方法。
• Synthesis of 7H-indolo[2,3-c]quinolines: study of the Pd-catalyzed intramolecular arylation of 3-(2-bromophenylamino)quinolines under microwave irradiation
  作者：Steven Hostyn、Bert U.W. Maes、Gitte Van Baelen、Anna Gulevskaya、Caroline Meyers、Koen Smits

  DOI：10.1016/j.tet.2005.12.062

  日期：2006.5

  methodology consists of two consecutive palladium-catalyzed reactions: a selective Buchwald–Hartwig amination followed by a regioselective intramolecular Heck-type reaction. The latter step has been investigated under microwave irradiation. Heating at 180 °C allows to seriously reduce the catalyst loading and get a full conversion to reaction product in 10 min. In addition, the former simplifies the

  D-环取代的5-甲基-5 H-吲哚并[2,3- c ]喹啉（4）已从市售的3-溴喹啉（5）和2-溴苯胺（6）开始分三步合成。该方法包括两个连续的钯催化反应：选择性布赫瓦尔德-哈特维希胺化反应，然后是区域选择性分子内Heck型反应。已在微波辐射下研究了后一步。加热到180°C可以严重减少催化剂的负载，并在10分钟内完全转化为反应产物。另外，前者简化了纯化。
• Trisubstitutedsilylphenoxyheterocycles and analogues
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：US10683311B2

  公开（公告）日：2020-06-16

  The present disclosure relates to fungicidal active compounds, more specifically to trisubstitutedsilylphenoxyhetero-cycles and analogues thereof, processes and, intermediates for their preparation and use thereof as fungicidal active compound, particularly in the form of fungicide compositions. The present disclosure also relates to methods for the control of phytopathogenic fungi of plants using these compounds or compositions comprising thereof.

  本公开涉及杀真菌活性化合物，更具体地说，涉及三取代硅基苯氧基杂环及其类似物、制备它们的工艺和中间体以及它们作为杀真菌活性化合物的用途，特别是以杀真菌剂组合物的形式。本公开还涉及使用这些化合物或包含这些化合物的组合物控制植物的植物病原真菌的方法。
• 具备光响应的基于磷光基元7H-吲哚[2,3-c]喹啉系列衍生物的制备方法
  申请人：北京化工大学

  公开号：CN117865953A

  公开（公告）日：2024-04-12

  具备光响应的基于磷光基元7H‑吲哚[2,3‑c]喹啉系列衍生物的制备方法属于有机智能材料领域。本发明中所提供的以NBCz为核心的几种有机磷光材料，在365nm紫外灯的不同光活化时间的影响下，都能实现从绿色或黄绿色余辉到橙黄色余辉的一个颜色转变，从而达到光诱导磷光颜色变化‑刺激性响应，所以可以广泛应用于防伪，数据加密和传感应用。这种以NBCz为核心的有机磷光材料，具有以下优点：(1)合成路线简单易行；(2)光活化条件简单；(3)斯托克斯位移大，效果显著。