8-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline | 1218306-21-8

• 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: 8-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline
• 英文别名: 8-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
• CAS: 1218306-21-8
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: UNMNWKGQNLOJGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 BENZAL-P-TOLUIDINE 在 4-nitrophthalic acid 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以82%的产率得到8-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline
  参考文献：
  名称：

  Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid

  摘要：

  4-Nitrophthalic acid was found to be an effective catalyst for the imino Diels-Alder reaction of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano- and furanoquinolines in good yields. It was also found that aryl amines react smoothly with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under the same condition to afford the corresponding pyrano- and furanoquinolines in high yields. This catalyst is inexpensive, easily available, water soluble, and stable to aqueous reaction conditions.

  DOI：

  10.1007/s00706-007-0765-4

文献信息

• Macrocycle-Enabled Counteranion Trapping for Improved Catalytic Efficiency
  作者：Rui Ning、Yu-Fei Ao、De-Xian Wang、Qi-Qiang Wang

  DOI：10.1002/chem.201800326

  日期：2018.3.20

  of the macrocycle can significantly improve the ethanedisulfonic acid‐catalyzed Povarov reaction efficiency, while the acyclic analogues had diminished effect. Catalysis outcomes and binding studies taken together suggested the macrocycle promotion was through favoring the substrate protonation by trapping the counteranion of the acid catalyst.

  功能性大环促成的紧密的宿主-客体结合可以用来调节催化作用。尽管强冠醚-阳离子络合已广泛用于增强配对阴离子的反应性，但仍未探索通过应用大环阴离子受体来捕获抗衡阴离子以提高阳离子催化活性的互补策略。为了实现该策略，合成了一个包含多个协同氢键位点的大环，并证明其将乙二磺酸根阴离子紧密捕集在晶体和乙腈溶液中（K > 10 6  m -1）。具有强结合趋势，低至0.25 mol％的大环化合物的存在可以显着提高乙烷二磺酸催化的Povarov反应效率，而无环类似物的作用减弱。催化结果和结合研究共同表明，大环化合物的促进是通过捕获酸催化剂的抗衡阴离子来促进底物质子化。
• Imino Diels-Alder Reactions: Efficient Synthesis of Pyrano- and Furanoquinolines Catalyzed by 4-Nitrophthalic Acid
  作者：Aswathanarayana Srinivasa、Kittappa Malavalli Mahadevan、Kallappa Mahadevappa Hosamani、Vijaykumar Hulikal

  DOI：10.1007/s00706-007-0765-4

  日期：2008.2

  4-Nitrophthalic acid was found to be an effective catalyst for the imino Diels-Alder reaction of N-benzylideneanilines with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano- and furanoquinolines in good yields. It was also found that aryl amines react smoothly with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under the same condition to afford the corresponding pyrano- and furanoquinolines in high yields. This catalyst is inexpensive, easily available, water soluble, and stable to aqueous reaction conditions.