1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)oct-2-yn-1-one | 1424284-37-6

• 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: 1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)oct-2-yn-1-one
• 英文别名: 1-(6-methoxy-3,4-dihydro-2H-quinolin-1-yl)oct-2-yn-1-one
• CAS: 1424284-37-6
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: CUMGXUXEGPJAMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)oct-2-yn-1-one 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以45%的产率得到2-iodo-1-pentyl-6,7-dihydro-3H-pyrrolo[2,1-j]quinoline-3,9(5H)-dione
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014
• 作为产物：
  描述：

  6-甲氧基-1,2,3,4-四氢喹啉 、 2-辛炔酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)oct-2-yn-1-one
  参考文献：
  名称：

  Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization

  摘要：

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.014

文献信息

• Synthesis of pyrrolo-[2,1-j]quinolone framework via intramolecular electrophilic ipso-cyclization
  作者：Lila Low-Beinart、Xiaohan Sun、Eli Sidman、Tanay Kesharwani

  DOI：10.1016/j.tetlet.2012.12.014

  日期：2013.3

  The challenging pyrrolo-12,1-j]quinolone core structure has been synthesized from N-(alkynoyl)-6-methoxytetrahydroquinoline in good yields using electrophilic cyclization as the key step. These reactions require simple starting materials and mild reaction conditions. In addition, we have demonstrated that the iodine moiety, which could be easily introduced in the final step, is very useful for further functionalization by employing various palladium-catalyzed cross-coupling reactions. (C) 2012 Elsevier Ltd. All rights reserved.