6-bromo-8-iodo-1,2,3,4-tetrahydroquinoline | 853021-67-7

• 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-bromo-8-iodo-1,2,3,4-tetrahydroquinoline
• 英文别名: 6-Bromo-8-iodo-1,2,3,4-tetrahydroquinoline
• CAS: 853021-67-7
• 化学式: C₉H₉BrIN
• 分子量: 337.986
• InChiKey: PNZVQFAKVJUWFP-UHFFFAOYSA-N

物化性质

• 沸点：
  365.7±42.0 °C(Predicted)
• 密度：
  1.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-8-iodo-1,2,3,4-tetrahydroquinoline 在 palladium dichloride bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 8-bromo-2-(3,5-dimethylphenyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline
  参考文献：
  名称：

  Palladium(II)-catalyzed heterocyclisation of 8-arylethynyl-1,2,3,4-tetrahydroquinolines: a facile route to 2-aryl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline derivatives

  摘要：

  Dihydropyrroloquinolines have been synthesized reacting 8-arylethynyl-1,2,3,4-tetrahydroquinolines in the presence of palladium(II) chloride catalyst. Heteroannulation has been achieved in good yields and tolerates substituents on the tetrahydroquinoline, including bromo, cyano, and ester. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.041
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 在 N-溴代丁二酰亚胺(NBS) 、 一氯化碘 、 calcium carbonate 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 反应 3.0h， 生成 6-bromo-8-iodo-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Palladium(II)-catalyzed heterocyclisation of 8-arylethynyl-1,2,3,4-tetrahydroquinolines: a facile route to 2-aryl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline derivatives

  摘要：

  Dihydropyrroloquinolines have been synthesized reacting 8-arylethynyl-1,2,3,4-tetrahydroquinolines in the presence of palladium(II) chloride catalyst. Heteroannulation has been achieved in good yields and tolerates substituents on the tetrahydroquinoline, including bromo, cyano, and ester. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.041

文献信息

• C–N bond forming reaction under copper catalysis: a new synthesis of 2-substituted 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolines
  作者：Mohosin Layek、A.V. Dhanunjaya Rao、Vikas Gajare、Dipak Kalita、Deepak Kumar Barange、Aminul Islam、K. Mukkanti、Manojit Pal

  DOI：10.1016/j.tetlet.2009.06.041

  日期：2009.8

  We report copper-catalyzed intramolecular cyclization of 8-alkynyl-1,2,3,4-tetrahydroquinolines, obtained via a Pd/C-mediated Sonogashira coupling in water, to afford 2-substituted 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolines. Further functionalization of the compounds synthesized was carried out under Heck, Sonogashira, and Suzuki reaction conditions. (c) 2009 Elsevier Ltd. All rights reserved.
• Palladium(II)-catalyzed heterocyclisation of 8-arylethynyl-1,2,3,4-tetrahydroquinolines: a facile route to 2-aryl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline derivatives
  作者：Pascal Marchand、Alain Puget、Guillaume Le Baut、Peter Emig、Michael Czech、Eckhard Günther

  DOI：10.1016/j.tet.2005.02.041

  日期：2005.4

  Dihydropyrroloquinolines have been synthesized reacting 8-arylethynyl-1,2,3,4-tetrahydroquinolines in the presence of palladium(II) chloride catalyst. Heteroannulation has been achieved in good yields and tolerates substituents on the tetrahydroquinoline, including bromo, cyano, and ester. (c) 2005 Elsevier Ltd. All rights reserved.