6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one | 1320360-56-2

• 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: 6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydro-1H-quinolin-4-one
• CAS: 1320360-56-2
• 化学式: C₁₅H₁₀Br₂FNO
• 分子量: 399.057
• InChiKey: VJJGTEPKHCFGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 potassium carbonate 、 thallium(III) p-tosylate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 21.0h， 生成 2-(4-fluorophenyl)-4-methoxy-6,8-diphenylquinoline
  参考文献：
  名称：

  Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones

  摘要：

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.085
• 作为产物：
  描述：

  邻氨基苯乙酮 在 磷酸 、 溴 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 6,8-dibromo-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies

  摘要：

  A series of novel 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones have been synthesized and evaluated in vitro (in MCF-7 breast cancer cell lines). Compounds 5a, 5d, 5e, and 5g exhibited potent GI(50) and TGI values compared with reference standard and compounds 5b and 5c showed moderate activity. The docking studies (in silico) were conducted to recognize the hypothetical binding motif of the title compounds within the active site of aromatase enzyme employing GOLD docking software. The binding mode and SAR of the title compounds has been proposed based on the docking studies.

  DOI：

  10.1007/s00044-011-9688-z

文献信息

• Reactivity of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones in a palladium catalyzed Sonogashira cross-coupling reaction
  作者：Malose Jack MPHAHLELE、Felix Adetunji OYEYIOLA

  DOI：10.3906/kim-1505-42

  日期：——

  Pd/C-PPh$_3}$--CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1$H)$-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4(1$H)$-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl$_2}$(PPh$_3})_2}$ was used as Pd(0) source. The monoalkynylated derivatives were, in turn, subjected to PdCl$_2}$ in acetonitrile under reflux to afford either the corresponding 2,4-diaryl-8-bromopyrrolo[3,2,1-\textitij}]quinolinones or the 8-(4-hydroxybutanoyl)-substituted quinolinone derivatives, exclusively. Suzuki--Miyaura cross-coupling of the 2-aryl-6-bromo-8-(alkynyl)quinolin-4-ones afforded the 2,4,8-trisubstituted pyrrolo[3,2,1-\textitij}]quinolin-6-ones.

  在Pd/C-PPh$_3}$--CuI催化的Sonogashira偶联反应中，2-芳基-6,8-二溴-2,3-二氢喹啉-4(1$H)$-酮与苯乙炔或3-丁炔-1-醇反应，专一性地得到相应的8-炔基喹啉-4(1$H)$-酮衍生物。当使用PdCl$_2}$(PPh$_3})_2}$作为Pd(0)源时，观察到双碳取代得到6,8-二炔基衍生物。单炔基化衍生物在回流条件下使用PdCl$_2}$在乙腈中进行反应，专一性地得到相应的2,4-二芳基-8-溴吡咯并[3,2,1-ij]喹啉酮或8-(4-羟基丁酰基)取代的喹啉酮衍生物。Suzuki--Miyaura偶联反应中，2-芳基-6-溴-8-(炔基)喹啉-4-酮得到2,4,8-三取代的吡咯并[3,2,1-ij]喹啉-6-酮。
• One-Pot Site-Selective Sonogashira Cross-Coupling–Heteroannulation of the 2-Aryl-6,8-Dibromoquinolin-4(1<i>H</i>)-Ones: Synthesis of Novel 6-<i>H</i>-Pyrrolo[3,2,1-<i>ij</i>]Quinolin-6-Ones
  作者：Malose J. Mphahlele、Felix A. Oyeyiola

  DOI：10.3184/174751914x14097554893763

  日期：2014.9

  The 2-aryl-6,8-dibromoquinolin-4(1 H)-ones were subjected to site-selective Sonogashira cross-coupling with terminal acetylenes as models for C sp²-C sp bond formation in the presence of Pd/C–PPh₃ and CuI as catalysts and K₂CO₃ as a base in dioxane to afford the 2-substituted 4-aryl-8-bromo-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones. These were, in turn, subjected to Suzuki–Miyaura cross-coupling with 4-fluorophenylboronic acid as coupling partner to afford the 2-substituted 4,8-diaryl-4 H-pyrrolo[3,2,1- ij]quinolin-6-ones.

  2- 芳基-6,8-二溴喹啉-4(1 H)-酮在二噁烷中，以 Pd/C-PPh3 和 CuI 为催化剂，以 K2CO3 为碱的存在下，与作为 C sp2-C sp 键形成模型的末端乙炔进行位点选择性 Sonogashira 交叉偶联，得到 2-取代的 4- 芳基-8-溴-4 H-吡咯并[3,2,1-ij]喹啉-6-酮。然后，以 4-氟苯硼酸为偶联剂，对这些化合物进行 Suzuki-Miyaura 交叉偶联，得到 2-取代的 4,8-二芳基-4H-吡咯并[3,2,1-ij]喹啉-6-酮。
• Synthesis and Photophysical Properties of 2-Aryl-6,8-bis(arylethenyl)-4-methoxyquinolines
  作者：Tebogo Khoza、Marole Maluleka、Neliswa Mama、Malose Mphahlele

  DOI：10.3390/molecules171214186

  日期：——

  Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxy-quinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-propen-1-ones reacted with iodine in methanol afford in a single pot operation the corresponding 2-aryl-6,8-dibromo-4-methoxyquinoline (major) and 2-aryl-6,8-dibromoquinolin-4(1H)-one (minor) products that were separated in sequence by column chromatography on silica gel. Suzuki-Miyaura cross-coupling of the 6,8-dibromo-4-methoxyquinoline derivatives with excess arylvinylboronic acids afforded the corresponding 2-aryl-6,8-bis(2-arylethenyl)-4-methoxyquinolines. The absorption and fluorescence properties of these compounds were also determined.

  碘-甲醇介导的2-芳基-6,8-二溴-2,3-二氢喹啉-4(1H)-酮的氧化芳构化以高浓度提供相应的2-芳基-6,8-二溴-4-甲氧基-喹啉。产量和纯度。异构体 1-(2-氨基-3,5-二溴苯基)-3-芳基-2-丙烯-1-酮在甲醇中与碘反应，在单锅操作中得到相应的 2-芳基-6,8-二溴- 4-甲氧基喹啉（主要）和2-芳基-6,8-二溴喹啉-4(1H)-酮（次要）产物，通过硅胶柱色谱依次分离。 6,8-二溴-4-甲氧基喹啉衍生物与过量芳基乙烯基硼酸的铃木-宫浦交叉偶联得到相应的2-芳基-6,8-双(2-芳基乙烯基)-4-甲氧基喹啉。还测定了这些化合物的吸收和荧光特性。
• Suzuki–Miyaura cross-coupling of 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones and subsequent dehydrogenation and oxidative aromatization of the resulting 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones
  作者：Malose J. Mphahlele、Felix A. Oyeyiola

  DOI：10.1016/j.tet.2011.06.085

  日期：2011.9

  Dichlorobis(triphenylphosphine)palladium(II)/tricyclohexylphosphine-catalyzed Suzuki-Miyaura cross-coupling of the 2-aryl-6,8-dibromo-1,2,3,4-tetrahydroquinolin-4-ones with arylboronic acids afforded the corresponding 2,6,8-triaryl-1,2,3,4-tetrahydroquinolin-4-ones, exclusively. The latter was subjected to thallium(III) p-tolylsulfonate (TTS) in dimethoxyethane under reflux or to molecular iodine in methanol at reflux to afford the 2,6,8-triarylquinolin-4-(1H)-ones and 2,6,8-triaryl-4-methoxyquinoline derivatives, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, evaluation of 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones in MCF-7 (breast cancer) cell lines and their docking studies
  作者：Lakshmi Narayana Bheemanapalli、Amandeep Kaur、Ramandish Arora、Sangeeta、Raghuram Rao Akkinepally、Narashima Murthy Javali

  DOI：10.1007/s00044-011-9688-z

  日期：2012.8

  A series of novel 6,8-dibromo-2-aryl-2,3-dihydroquinolin-4(1H)-ones have been synthesized and evaluated in vitro (in MCF-7 breast cancer cell lines). Compounds 5a, 5d, 5e, and 5g exhibited potent GI(50) and TGI values compared with reference standard and compounds 5b and 5c showed moderate activity. The docking studies (in silico) were conducted to recognize the hypothetical binding motif of the title compounds within the active site of aromatase enzyme employing GOLD docking software. The binding mode and SAR of the title compounds has been proposed based on the docking studies.