6-amino-5-bromo-1-ethylquinolin-2(1H)-one | 1283075-82-0

• 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: 6-amino-5-bromo-1-ethylquinolin-2(1H)-one
• 英文别名: 6-Amino-5-bromo-1-ethylquinolin-2-one
• CAS: 1283075-82-0
• 化学式: C₁₁H₁₁BrN₂O
• 分子量: 267.125
• InChiKey: DANBBQUDYIWVKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-5-bromo-1-ethylquinolin-2(1H)-one 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到6-amino-1-ethyl-5-(3-hydroxy-3-methylbut-1-ynyl)quinolin-2(1H)-one
  参考文献：
  名称：

  分子碘对吡喃并[3,2- f ]喹啉和菲咯啉衍生物的区域选择性合成

  摘要：

  已经通过分子碘催化具有或不具有取代胺的各种炔丙醇的串联催化合成了一系列多取代的吡喃并[3,2- f ]喹啉和菲咯啉衍生物。此外，环化副产物也是吡喃并[3，2- f ]喹啉和菲咯啉衍生物。

  DOI：

  10.1016/j.tetlet.2013.07.163
• 作为产物：
  描述：

  6-amino-1-ethylquinolin-2(1H)-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 生成 6-amino-5-bromo-1-ethylquinolin-2(1H)-one
  参考文献：
  名称：

  分子碘对吡喃并[3,2- f ]喹啉和菲咯啉衍生物的区域选择性合成

  摘要：

  已经通过分子碘催化具有或不具有取代胺的各种炔丙醇的串联催化合成了一系列多取代的吡喃并[3,2- f ]喹啉和菲咯啉衍生物。此外，环化副产物也是吡喃并[3，2- f ]喹啉和菲咯啉衍生物。

  DOI：

  10.1016/j.tetlet.2013.07.163

文献信息

• Copper(II) Triflate Promoted One-Pot Synthesis of Coumarin-, Quinolone-, and Naphthalene-Annulated 2-Aminothiazoles under Ligand-Free Conditions
  作者：K. Majumdar、Nirupam De、Debankan Ghosh、Sudipta Ponra、B. Roy

  DOI：10.1055/s-0031-1289608

  日期：2012.1

  An efficient synthesis of new 2-aminothiazole-annulated compounds is described via copper(II) triflate promoted sequential condensation, arylation, and heterocyclization reactions in one step. The reaction is compatible with a variety of substrates providing efficient access to many biologically important skeletons in good yields. copper triflate - multicomponent reaction - naphthothiazole - domino

  通过三氟甲磺酸铜（II）一步一步促进顺序缩合，芳基化和杂环化反应，描述了一种新型的2-氨基噻唑环化化合物的有效合成方法。该反应与多种底物相容，从而以高收率有效地接近许多生物学上重要的骨架。 三氟甲磺酸铜-多组分反应-萘噻唑-多米诺合成-二硫化碳
• Synthesis of pyrrolo[1,2-f]phenanthridine-annulated polycyclic heterocycles from palladium-catalyzed intramolecular direct arylation reaction
  作者：Brindaban Roy、Rajendra Narayan De、Somjit Hazra

  DOI：10.1007/s00706-011-0564-9

  日期：2012.1

  AbstractA concise synthesis of pyrrolo[1,2-f]phenanthridine-annulated polycyclic heterocycles has been achieved in good yields by palladium-catalyzed intramolecular direct arylation reaction. Graphical abstract

  摘要通过钯催化的分子内直接芳基化反应，可以高收率合成吡咯并[1,2 - f ]菲啶环化的多环杂环。 图形概要
• Iron/Palladium-Catalyzed Intramolecular Hydroamination: An Expedient Synthesis of Pyrrole-Annulated Coumarin and Quinolone Derivatives
  作者：K. Majumdar、Nirupam De、B. Roy

  DOI：10.1055/s-0030-1258311

  日期：2010.12

  A highly efficient intramolecular hydroamination reaction of heterocycle-centered aminoalkynes using both substituted and free amines catalyzed by PdCl2/FeCl3 catalytic system to form the biologically important pyrrolocoumarin and pyrroloquinolone derivatives is reported. The use of both aliphatic and aromatic substituted alkynes with different heterocyclic skleton in this strategy demonstrated the

  报道了使用PdCl 2 / FeCl 3催化体系催化的取代胺和游离胺对以杂环为中心的氨基炔烃进行的高效分子内加氢胺化反应，以形成生物学上重要的吡咯香豆素和吡咯并喹诺酮衍生物。在该策略中同时使用具有不同杂环骨架的脂族和芳族取代炔烃证明了该方法的多样性。 加氢胺化-吡咯并香豆素-吡咯并喹诺酮-FeCl 3-氨基炔
• Synthesis of novel pyrano[3,2-f]quinoline, phenanthroline derivatives and studies of their interactions with proteins: An application in mammalian cell imaging
  作者：K.C. Majumdar、Sudipta Ponra、Tapas Ghosh、Ratan Sadhukhan、Utpal Ghosh

  DOI：10.1016/j.ejmech.2013.10.067

  日期：2014.1

  A series of tri-cyclic pyrano[3,2-f]quinoline and phenanthroline derivatives have been synthesized by a HCl-mediated 6-'endo-trig' Michael type ring closure reaction of 6-amino-5-(3-hydroxy-3-methylbut-1-ynyl)-2H-chromen-2-one in excellent yields. The process is very simple, facile and inexpensive and can provide a diverse range of substituted quinoline derivatives from simple and easily available starting materials. Moreover, the synthesized derivatives exhibit staining property to the cultured HeLa cells after fixing and can be used as fluorophores which can bind with protein molecule. (C) 2013 Published by Elsevier Masson SAS.
• Green, One-Pot, Multicomponent Synthesis of Fused-Ring 2-Aminothiazoles
  作者：Siddique Anwar、Satya B. Paul、K. C. Majumdar、Sudip Choudhury

  DOI：10.1080/00397911.2014.904880

  日期：2014.11.17

  A facile, green, and efficient Fe(III) chloride, one-pot, multicomponent reaction (MCR) for synthesis of 2-aminothiazole-based compounds is reported. Considering the medicinal importance of fused ring 2-aminothiazoles, this process provides an easy route to the synthesis of this class of compound. Detailed mechanism of the reaction has been discussed.