| 1421590-19-3

• 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
• CAS: 1421590-19-3
• 化学式: C₁₅H₈Br₂ClNO
• 分子量: 413.496
• InChiKey: AMQUNHMJIYRPNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

文献信息

• 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。