2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-8-fluoro-furo[3,2-c]quinoline

• 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: 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-8-fluoro-furo[3,2-c]quinoline
• 英文别名: 3-[(3aR,4R,9bR)-8-fluoro-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinolin-4-yl]propan-1-ol
• 化学式: C₁₄H₁₈FNO₂
• 分子量: 251.301
• InChiKey: CAUFTYVPCDFEKA-MPKXVKKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 4-氟苯胺 在 Montmorillonite KSF 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-8-fluoro-furo[3,2-c]quinoline 、 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-8-fluoro-furo[3,2-c]quinoline
  参考文献：
  名称：

  蒙脱土粘土催化的[4 + 2]环加成反应：吡喃基和呋喃基喹啉的简便合成

  摘要：

  在温和的反应条件下，芳基胺与蒙脱石KSF表面的环状烯醇醚（例如3,4-二氢-2 H-吡喃（DHP）和2,3-二氢呋喃（DHF））平稳反应，得到相应的吡喃和呋喃[3,2- c ]喹啉具有高收率和高非对映选择性。

  DOI：

  10.1016/s0040-4039(02)00679-2

文献信息

• InCl₃-Catalyzed Domino Reaction of Aromatic Amines with Cyclic Enol Ethers in Water:  A Highly Efficient Synthesis of New 1,2,3,4-Tetrahydroquinoline Derivatives
  作者：Jianheng Zhang、Chao-Jun Li

  DOI：10.1021/jo020131d

  日期：2002.5.1

  structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers or 2-hydroxy cyclic ether catalyzed by indium chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclization products showed cis selectivity. The use of 2,3-dihydrofuran as the cyclic enol ether provided both higher reactivity and cis selectivity than

  四氢喹啉部分是许多天然产物的结构特征。通过在水中用氯化铟催化芳香胺与环状烯醇醚或2-羟基环状醚的多米诺反应，可以有效地合成各种四氢喹啉衍生物。大多数环化产物显示出顺式选择性。与使用3,4-二氢-2H-吡喃相比，使用2,3-二氢呋喃作为环状烯醇醚提供更高的反应性和顺式选择性。由于控制水中的螯合作用，使顺式选择性暂定合理。
• A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers
  作者：Xu-Feng Lin、Sun-Liang Cui、Yan-Guang Wang

  DOI：10.1016/j.tetlet.2006.03.123

  日期：2006.6

  A highly efficient method for the synthesis of 1,2,3,4-tetrahydroquinoline derivatives via a molecular iodine catalyzed domino reaction of anilines with cyclic enol ethers, such as 2,3-dihydrofuran and 3,4-dihydro-2H-pyran, is described. The reaction may proceed through an aza-Diels–Alder process between an in situ generated 2-azadiene and another equivalent of cyclic enol.

  通过分子碘催化苯胺与环状烯醇醚（例如2,3-二氢呋喃和3,4-二氢-2 H-吡喃）的分子碘催化的多米诺反应，合成1,2,3,4-四氢喹啉衍生物的高效方法进行说明。该反应可通过原位生成的2-氮杂二烯与另一当量的环状烯醇之间的aza-Diels-Alder过程进行。
• InCl3-catalyzed reaction of aromatic amines with cyclic hemiacetals in water: facile synthesis 1,2,3,4-tetrahydroquinoline derivatives
  作者：Zigang Li、Jianheng Zhang、Chao-Jun Li

  DOI：10.1016/s0040-4039(02)02450-4

  日期：2003.1

  By using a domino reaction of aromatic amines with various cyclic hemiacetals catalyzed by indium chloride in water, tetrahydroquinoline derivatives were synthesized efficiently.

  通过使用芳族胺与氯化铟在水中催化的各种环状半缩醛的多米诺反应，可以有效地合成四氢喹啉衍生物。
• Low-Temperature Synthesis of Pyrano- and Furo[3,2-c]quinolines via Povarov Reaction Using a Highly Ordered 3D Nanoporous Catalyst with a High Acidity
  作者：A. Vinu、S. Chauhan、G. Mane、C. Anand、D. Dhawale、B. Reddy、S. Zaidi、Salem Al-Deyab、V. Balasubramanian、T. Mori

  DOI：10.1055/s-0031-1290452

  日期：——

  The imines generated in situ from aryl amines and cyclic enol ethers undergo smooth [4+2] cycloaddition with 3,4-dihydro-2H-pyran (DHP) and 2,3-dihydrofuran (DHF) using the Bronsted acid sites on the aluminosilicate wall structure of the nanoporous catalyst under mild reaction conditions to afford the corresponding pyrano- and furo[3,2-c]quinolines, respectively, in good yields with high diastereoselectivity. The high activity of the catalyst is due to its high surface area, large pore volume, and well-ordered porous structure with high acidity. In addition, the catalyst was found to be highly stable and can be reused several times without affecting the activity of the catalyst.
• Sm(III)nitrate-catalyzed one-pot synthesis of furano[3,2c]-1,2,3,4-tetrahydroquinolines and DNA photocleavage studies
  作者：P.J. Bindu、K.M. Mahadevan、T.R. Ravikumar Naik

  DOI：10.1016/j.molstruc.2012.03.064

  日期：2012.8

  The synthesis and DNA photocleavage studies of furano[3,2-c]-1,2,3,4-tetrahydroquinolines have been reported. Sm(III)nitrate was found to be an efficient for the Diels-Alder reaction of aryl amines with 2,3-dihydrofuran to offer the corresponding furano[3,2-c]-1,2,3,4-tetrahydroquinolines derivatives as a mixture of cis/trans stereoisomers in moderate yields. The aqueous solubility of acid catalyst can be recycled without significant loss of activity. The DNA photocleavage studies shows that, the cis/trans stereoisomers are good DNA cleavage mimic in terms of molecular structure. (C) 2012 Elsevier B.V. All rights reserved.