ethyl 4‐(2,3‐dichlorophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate

• 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: ethyl 4‐(2,3‐dichlorophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate
• 英文别名: Ethyl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• 化学式: C₂₁H₂₃Cl₂NO₃
• 分子量: 408.325
• InChiKey: ANDGKTHYGNUQRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 5,5-二甲基-1,3-环己二酮 、 2,3-二氯苯甲醛 在 [Fe-(E)-6-(2-hydroxybenzylideneamino)-3-methyl-4-phenyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile]Cl₂ 、 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.08h， 以80%的产率得到ethyl 4‐(2,3‐dichlorophenyl)‐2,7,7‐trimethyl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate
  参考文献：
  名称：

  纳米铁[苯基-水杨基亚胺-甲基吡喃并吡唑] Cl2作为席夫碱配合物和纳米结构催化剂在六氢喹啉合成中的催化应用

  摘要：

  通过苯乙醛与乙酰乙酸乙酯，丙二腈和水合肼的四组分缩合反应，使用FeCl 2合成吡喃并吡唑衍生物，然后与水杨醛反应生成纳米Fe- [苯基-水杨醛亚胺-甲基吡咯并唑] Cl 2（纳米[Fe-PSMP] Cl 2）。制备的纳米席夫碱配合物已成功用作合成六氢喹啉的有效催化剂。

  DOI：

  10.1002/jccs.201700211

文献信息

• TEDETA@BNPs as a basic and metal free nanocatalyst for Knoevenagel condensation and Hantzsch reaction
  作者：Arash Ghorbani-Choghamarani、Zahra Heidarnezhad、Bahman Tahmasbi、Gouhar Azadi

  DOI：10.1007/s13738-018-1417-9

  日期：2018.10

  In this work, Boehmite nanoparticles (BNPs) were synthesized in water using commercially available materials and further N,N,N′,N′-tetraethyldiethylentriamin (TEDETA) was supported on the surface of BNPs, and used as organo-basic catalyst in four-component Hantzsch reaction that provides access to pharmaceutically polyhydroquinoline derivatives and Knoevenagel reaction to afford α,β-unsaturated compounds. All products were obtained in excellent yields (89–98%) and good reaction times under green condition such as water and ethanol solvents. This catalyst was characterized using FT-IR, SEM, EDS, and TGA techniques. This catalyst was reused for several times without the significant loss of their catalytic efficiency. In addition, stability of catalyst after recycling was confirmed by TGA, SEM, EDS and FT-IR techniques.

  在这项工作中，采用商业可得的材料在水中合成了水铝石纳米粒子（BNPs），并进一步在BNPs表面负载了N,N,N′,N′-四乙基二乙烯三胺（TEDETA），用于四组分汉茨施反应中的有机碱催化剂，从而获得制药用的多氢喹啉衍生物，并开展克诺文那尔反应以得到α,β-不饱和化合物。所有产物均在绿色条件下如水和乙醇溶剂中以优异的产率（89-98%）和良好的反应时间获得。该催化剂采用FT-IR、SEM、EDS和TGA技术进行表征。该催化剂在多次重复使用后，其催化效率未显著降低。此外，通过TGA、SEM、EDS和FT-IR技术确认了催化剂再生后仍具有良好的稳定性。
• Preparation and characterization of Cu (II) supported on poly(8-hydroxyquinoline-<i>p</i> -styrene sulphonate) and its application as catalyst for the synthesis of hexahydroquinolines
  作者：Ardeshir Khazaei、Mahsa Tavasoli、Vahid Jamshidi、Fatemeh Gohari Ghalil、Ahmad Reza Moosavi-Zare

  DOI：10.1002/aoc.4368

  日期：2018.7

  Cu (II) supported on poly(8‐hydroxyquinoline‐p‐styrenesulfonate) (Cu (II)@PHQSS) was prepared and fully characterized by the different techniques including fourier transform infrared spectroscopy (FT‐IR), 1H NMR, 13C NMR, thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), differential thermal analysis (DTA), scanning electron microscope (SEM) and energy dispersive X‐ray analysis

  的Cu（II）负载在聚（8- hydroxyquinoline- p -styrenesulfonate）（铜（II）@PHQSS）溶液并充分表征由不同的技术，包括傅里叶变换红外光谱（FT-IR），1 H NMR，13 C ^ NMR，热重分析（TGA），差热重分析（DTG），差热分析（​​DTA），扫描电子显微镜（SEM）和能量色散X射线分析（EDS）。然后，将Cu（II）@PHQSS作为纳米结构催化剂用作合成六氢喹啉的催化剂。
• Catalytic Applications of Nano-Fe-[Phenyl-Salicylaldimine-Methylpyranopyrazole]Cl₂as a Schiff Base Complex and Nanostructured Catalyst for the Synthesis of Hexahydroquinolines
  作者：Hamid Goudarziafshar、Ahmad Reza Moosavi-Zare、Khadijeh Saki、Mehdi Abdolmaleki

  DOI：10.1002/jccs.201700211

  日期：2017.12

  reaction of benzaldehyde with ethyl acetoacetate, malononitrile, and hydrazine hydrate using FeCl2, a pyranopyrazole derivative was synthesized and then reacted with salicylaldehyde to give nano‐Fe‐[phenyl‐salicylaldimine‐methylpyranopyrazole]Cl2 (nano‐[Fe‐PSMP]Cl2). The prepared nano‐Schiff base complex was successfully used as an efficient catalyst for the synthesis of hexahydroquinolines.

  通过苯乙醛与乙酰乙酸乙酯，丙二腈和水合肼的四组分缩合反应，使用FeCl 2合成吡喃并吡唑衍生物，然后与水杨醛反应生成纳米Fe- [苯基-水杨醛亚胺-甲基吡咯并唑] Cl 2（纳米[Fe-PSMP] Cl 2）。制备的纳米席夫碱配合物已成功用作合成六氢喹啉的有效催化剂。
• Praseodymium(<scp>iii</scp>) anchored on CoFe₂O₄ MNPs: an efficient heterogeneous magnetic nanocatalyst for one-pot, multi-component domino synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1<i>H</i>)-one derivatives
  作者：Taiebeh Tamoradi、Seyedeh Masoumeh Mousavi、Masoud Mohammadi

  DOI：10.1039/c9nj05468e

  日期：——

  available materials is reported. The prepared samples were characterized by chemical and physical methods such as FTIR, SEM, XRD and EDX and were tested in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives. It was observed that the yields of the reactions in the presence of the prepared nanocatalyst were good to excellent. More importantly, the use of a recoverable

  在本研究中，报告了一种通过使用可用材料将technique（III）配合物固定在磁性纳米颗粒表面的简便技术。所制备的样品通过化学和物理方法（如FTIR，SEM，XRD和EDX）进行表征，并在合成聚氢喹啉和2,3-二氢喹唑啉-4（1 H）-one衍生物中进行了测试。观察到，在制备的纳米催化剂的存在下，反应的产率良好至优异。更重要的是，在这些反应中使用可回收的新型磁性纳米催化剂是该方案的突出特点。
• Synthesis, characterization and application of nano-CoAl₂ O₄ as an efficient catalyst in the preparation of hexahydroquinolines
  作者：Ardeshir Khazaei、Leila Jafari-Ghalebabakhani、Esmaeil Ghaderi、Mahsa Tavasoli、Ahmad Reza Moosavi-Zare

  DOI：10.1002/aoc.3815

  日期：2017.12

  analysis (EDX), X‐ray diffraction patterns (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM) and transmission electron microscopy (TEM). Nano‐CoAl2O4 was applied for the synthesis of hexahydroquinoline derivatives by the condensation reaction between ethyl acetoacetate, dimedone and various aldehydes. These reactions were carried out at 80 °C under solvent‐free conditions.

  在这项工作中，制备了纳米CoAl 2 O 4并通过FT-IR，能量色散X-射线分析（EDX），X-射线衍射图（XRD），扫描电子显微镜（SEM），振动样品磁力计（VSM）进行了表征）和透射电子显微镜（TEM）。通过乙酰乙酸乙酯，二甲酮与各种醛的缩合反应，将纳米CoAl 2 O 4用于合成六氢喹啉衍生物。这些反应在无溶剂条件下于80°C进行。