5-(6-Bromo-1,2,3,4-tetrahydroquinolin-8-yl)pent-4-yn-1-ol | 1186131-56-5

• 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: 5-(6-Bromo-1,2,3,4-tetrahydroquinolin-8-yl)pent-4-yn-1-ol
• 英文别名: 5-(6-bromo-1,2,3,4-tetrahydroquinolin-8-yl)pent-4-yn-1-ol
• CAS: 1186131-56-5
• 化学式: C₁₄H₁₆BrNO
• 分子量: 294.191
• InChiKey: NJTCEVDQGWXGNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(6-Bromo-1,2,3,4-tetrahydroquinolin-8-yl)pent-4-yn-1-ol 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以57%的产率得到3-(6-Bromo-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-2-yl)propan-1-ol
  参考文献：
  名称：

  C–N bond forming reaction under copper catalysis: a new synthesis of 2-substituted 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.06.041
• 作为产物：
  描述：

  6-bromo-8-iodo-1,2,3,4-tetrahydroquinoline 、 4-戊炔-1-醇 在 copper(l) iodide 、 palladium 10% on activated carbon 、 C.I.酸性橙108 、 三苯基膦 作用下， 以 水 为溶剂， 反应 18.0h， 以51%的产率得到5-(6-Bromo-1,2,3,4-tetrahydroquinolin-8-yl)pent-4-yn-1-ol
  参考文献：
  名称：

  C–N bond forming reaction under copper catalysis: a new synthesis of 2-substituted 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.06.041

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.