4-(4-bromo-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester | 292853-25-9

• 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: 4-(4-bromo-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8 hexahydroquinoline-3-carboxylate；2,7,7-trimethyl-5-oxo-4-(4-bromophenyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester；Ethyl 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate；ethyl 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,6,8-tetrahydroquinoline-3-carboxylate
• CAS: 292853-25-9
• 化学式: C₂₁H₂₄BrNO₃
• 分子量: 418.33
• InChiKey: WOXHNBDGNUVWNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 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

• 作为反应物：
  描述：

  4-(4-bromo-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester 在 甲醇 、 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 1.67h， 生成 ethyl 4-(4-(4-hydroxyphenyl)phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and 3D-QSAR studies of novel 1,4-dihydropyridines as TGFβ/Smad inhibitors

  摘要：

  Targeting TGF beta/Smad signaling is an attractive strategy for several therapeutic applications given its role as a key player in many pathologies, including cancer, autoimmune diseases and fibrosis. The class of b-annelated 1,4-dihydropyridines (DHPs) represents promising novel pharmacological tools as they interfere with this pathway in a novel fashion, i.e. through induction of TGF beta receptor type II degradation. In the present work, >40 rationally designed, novel DHPs were synthesized and evaluated for TGF beta inhibition, substantially expanding the current understanding of the SAR profile. Key findings include that the 2-position tolerates a wide variety of polar functionalities, suggesting that this region could possibly be solvent-exposed within the (thus far) unknown cellular target. A structural explanation for pathway selectivity is provided based on a diverse series of 4"-substituted DHPs, including molecular electrostatic potential (MEP) calculations. Moreover, the absolute configuration for the chiral 4-position was determined by X-ray crystal analysis and revealed that the bioactive (+)-enantiomers are (R)configured. Another key objective was to establish a 3D-QSAR model which turned out to be robust (r(2) = 0.93) with a good predictive power (r(pred)(2) = 0.69). This data further reinforces the hypothesis that this type of DHPs exerts its novel TGF beta inhibitory mode of action through binding a distinct target and that unspecific activities that would derive from intrinsic properties of the ligands (e.g., lipophilicity) play a negligible role. Therefore, the present study provides a solid basis for further ligand-based design of additional analogs or DHP scaffold-derived compounds for hit-to-lead optimization, required for more comprehensive pharmacological studies in vivo. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.027
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,2'-(4-bromophenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) 在 ammonium acetate 、 四丁基溴化铵 、 sodium carbonate 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以88%的产率得到4-(4-bromo-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  钯（0）纳米颗粒：一种一锅合成聚氢喹啉的有效催化剂

  摘要：

  描述了一种温和，简洁，有效的方案，该方案通过使用Pd纳米粒子通过芳族醛，二甲酮，乙酰乙酸乙酯或氰基乙酸乙酯和乙酸铵的四组分反应合成聚氢喹啉。在一个锅中的芳基亚甲基双（3-羟基-2-环己烯-1-酮），乙酰乙酸乙酯，乙酸铵和Pd-纳米颗粒中也观察到相同的现象。本方法还允许我们从简单且容易获得的输入中合成高度官能化的标题化合物。

  DOI：

  10.1016/j.tetlet.2011.07.031

文献信息

• Heterogeneous Cu(<scp>ii</scp>)/<scp>l</scp>-His@Fe₃O₄ nanocatalyst: a novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents
  作者：Masoomeh Norouzi、Arash Ghorbani-Choghamarani、Mohsen Nikoorazm

  DOI：10.1039/c6ra19776k

  日期：——

  A novel, efficient and green Cu(II)/L-His@Fe3O4 catalyst has been applied successfully in the synthesis of heterocyclic compounds. The resulting catalyst was used in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, polyhydroquinolines and 2-amino-6-(arylthio)pyridine-3,5-dicarbonitriles as biologically interesting compounds. The present research is focused on investigation of recycling, reusability

  一种新颖，高效，绿色的Cu（II）/ L- His @ Fe 3 O 4催化剂已成功用于杂环化合物的合成。所得催化剂用于合成2，3-二氢喹唑啉-4（1H）-酮，聚氢喹啉和2-氨基-6-（芳硫基）吡啶-3，5-二碳腈作为生物学上感兴趣的化合物。本研究的重点是研究相反应中催化剂的循环利用，可重复使用性和稳定性。Cu（II）/ L -His @ Fe 3 O 4该催化剂至少使用了六次，其活性与新鲜催化剂相当。通过TGA / DTG，EDS，XRD，VSM，FT-IR和SEM对催化剂的化学组成和结构进行了分析。
• Cu-<i>S</i>-(propyl)-2-aminobenzothioate on magnetic nanoparticles: highly efficient and reusable catalyst for synthesis of polyhydroquinoline derivatives and oxidation of sulfides
  作者：Arash Ghorbani-Choghamarani、Bahman Tahmasbi、Parisa Moradi、Nasrin Havasi

  DOI：10.1002/aoc.3478

  日期：2016.8

  Cu–S‐(propyl)‐2‐aminobenzothioate supported on functionalized Fe3O4 magnetic nanoparticles is reported as a reusable and highly efficient nanocatalyst for the one‐pot synthesis of polyhydroquinoline derivatives and also for selective oxidation of sulfides to sulfoxides. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric

  官能化的Fe 3 O 4上负载的Cu- S-（丙基）-2-氨基苯甲硫醇据报道，磁性纳米颗粒是一种可重复使用的高效纳米催化剂，可用于单锅合成多氢喹啉衍生物，也可用于将硫化物选择性氧化为亚砜。使用傅里叶变换红外光谱仪，振动样品磁力分析，热重分析，透射和扫描电子显微镜，能量色散X射线光谱，X射线衍射，电感耦合等离子体原子发射光谱和原子吸收光谱对制备的纳米颗粒进行表征。使用外部磁体可以容易地回收纳米催化剂，并且可以在不显着损失其催化效率的情况下重复使用几次。版权所有©2016 John Wiley＆Sons，Ltd.
• Polyhydroquinolines: 1-sulfopyridinium chloride catalyzed an efficient one-pot multicomponent synthesis via Hantzsch condensation under solvent-free conditions
  作者：B. Sakram、B. Sonyanaik、K. Ashok、S. Rambabu

  DOI：10.1007/s11164-016-2559-y

  日期：2016.10

  construction of polyhydroquinoline derivatives via one-pot, four-component Hantzsch condensation of various aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate in the presence of an ionic liquid, 1-sulpopyridinium chloride, as a catalyst under solvent-free conditions. This methodology has an advantage of high yields, short reaction times, a clean reaction profile, and reusability of the catalyst.

  摘要研究了 一种简单高效的方法，在离子液体1-磺基吡啶鎓氯化物存在下，通过一锅四组分的多种醛，二甲酮，乙酰乙酸乙酯和乙酸铵的汉茨缩合反应来构建聚氢喹啉衍生物。 ，在无溶剂条件下用作催化剂。该方法的优点是高产率，短反应时间，干净的反应曲线和催化剂的可重复使用性。 图形概要
• Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions
  作者：Arash Ghorbani-Choghamarani、Masoud Mohammadi、Lotfi Shiri、Zahra Taherinia

  DOI：10.1007/s11164-019-03930-0

  日期：2019.11

  The spinel ferrite FeAl2O4 (hercynite) MNPs (magnetic nanoparticles) were applied as a reusable catalytic system for the one-pot synthesis of benzo[ a ]pyrano[2,3-c] phenazine and polyhydroquinoline derivatives via a multicomponent reaction under green reaction conditions. The structure of the prepared nanocatalyst has been characterized by XRD, FTIR, SEM, EDS, BET, and VSM techniques. The FeAl2O4

  尖晶石型铁氧体FeAl 2 O 4（水铁矿）MNP（磁性纳米粒子）被用作可重复使用的催化体系，用于在以下条件下通过多组分反应一锅合成苯并[ a ]吡喃并[2,3-c]吩嗪和聚氢喹啉衍生物。绿色反应条件。制备的纳米催化剂的结构已通过XRD，FTIR，SEM，EDS，BET和VSM技术进行了表征。FeAl 2 O 4 MNP起到路易斯酸的作用，并具有许多优点，例如产物的收率高，反应时间短和后处理程序容易。此外，再循环的纳米催化剂被使用了至少四次而其活性没有明显损失。
• Introduction of an efficient DABCO-based bis-dicationic ionic salt catalyst for the synthesis of arylidenemalononitrile, pyran and polyhydroquinoline derivatives
  作者：Mehdi Zabihzadeh、Atefeh Omidi、Farhad Shirini、Hassan Tajik、Mohaddeseh Safarpoor Nikoo Langarudi

  DOI：10.1016/j.molstruc.2020.127730

  日期：2020.4

  Abstract —An affordable DABCO-based bis-dicationic ionic salt ([(DABCO)2C3H5OH]·2Cl) was utilized for the synthesis of arylidenemalononitrile, tetrahydrobenzo[b]pyran, pyrano[2,3-d]-pyrimidinone (thione), dihydropyrano[3,2-c]chromene, and polyhydroquinoline derivatives. The significant features of the presented method are ease of preparation and handling of the catalyst, high catalytic activity, short

  摘要 —一种经济实惠的基于 DABCO 的双阳离子离子盐 ([(DABCO)2C3H5OH]·2Cl) 用于合成亚芳基丙二腈、四氢苯并[b]吡喃、吡喃并[2,3-d]-嘧啶酮（硫酮），二氢吡喃并[3,2-c]色烯和聚氢喹啉衍生物。该方法的显着特点是催化剂易于制备和处理，催化活性高，反应时间短，无需柱色谱分离，后处理程序简单。此外，催化剂可以很容易地回收并在研究的反应中重复使用几个循环。