dimethyl 6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate | 1310688-82-4

• 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: dimethyl 6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
• 英文别名: dimethyl 6-methoxy-2-methyl-1H-quinoline-2,4-dicarboxylate
• CAS: 1310688-82-4
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: ZFYBQFQWZWJUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲氧苯胺 在 N-氯代丁二酰亚胺 、 O,O-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) hydrazine-1,2-bis(carbothioate) 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 dimethyl 6-methoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate
  参考文献：
  名称：

  Highly efficient synthesis of polysubstituted 1,2-dihydroquinolines via tandem reaction of α-ketoesters and arylamines catalyzed by fluorous hydrazine-1,2-bis(carbothioate) and NCS

  摘要：

  A simple and convenient tandem reaction of alpha-ketoesters with primary or secondary aromatic amines for the synthesis of polysubstituted 1,2-dihydroquinolines has been developed. The catalytic system (fluorous hydrazine-1,2-bis(carbothioate)/NCS) of the reaction has the advantages of operational simplicity, high efficiency, as well as easy recyclability. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.143

文献信息

• Synthesis and biological activity of fibrate-based acyl- and alkyl-phenoxyacetic methyl esters and 1,2-dihydroquinolines
  作者：Abraham Pucheta、Aarón Mendieta、Damián A. Madrigal、Roberto I. Hernández-Benitez、Liseth Romero、Leticia Garduño-Siciliano、Catalina Rugerio-Escalona、María C. Cruz-López、Fabiola Jiménez、Alejandra Ramírez-Villalva、Aydeé Fuentes-Benites、Carlos González-Romero、Omar Gómez-García、Julio López、Miguel A. Vázquez、Blanca Rosales-Acosta、Lourdes Villa-Tanaca、Alfonso Sequeda-Juárez、Eva Ramón-Gallegos、Germán Chamorro-Cevallos、Francisco Delgado、Joaquín Tamariz

  DOI：10.1007/s00044-019-02496-1

  日期：2020.3

  constituted by a fibrate-based structure was recently reported by our group, whose synthesis started from isovanillin derivatives. In the interest of evaluating the bioisosteric effect of the vanillin-based isomers on their antihyperlipidemic activity, the present study focuses on the synthesis of 5-acyl-1-phenoxyacetic methyl esters 5a–c and their saturated side-chain 5-alkyl-1-phenoxyacetates 6a–c. Their

  我们的小组最近报道了由基于纤维状结构的一系列高效降血脂药，其合成从异香草醛衍生物开始。为了评估基于香草醛的异构体对它们的降血脂活性的生物立体效应，本研究着重于5-酰基-1-苯氧基乙酸甲酯5a - c及其饱和侧链5-烷基-1的合成-苯氧乙酸酯6a – c。它们强大的体内作用与抑制HMG-CoA还原酶有关。由于1,2-二氢喹啉可抑制该酶，因此一系列此类杂环（9a – d）是通过我们有效的区域选择性，一步一步，无溶剂的方法制备的。除了在体内表现出降血脂活性外，某些化合物在体外还表现出抗真菌，抗氧化剂和细胞毒活性。通过对接模拟检查了四种化合物在HMGRh活性位点的结合模式，观察到与辛伐他汀靶向的大多数氨基酸发生相互作用。
• An efficient method for the preparation of 2,2,4-trisubstituted 1,2-dihydroquinolines using catalytic amount Bi(OTf)3 as catalyst
  作者：Zeynep Gültekin、Wolfgang Frey

  DOI：10.3998/ark.5550190.0013.822

  日期：——

  Substituted 1,2-dihydroquinolines have been synthesised from substituted anilines and methyl pyruvate using catalytic amounts of commercially available Bi(OTf)3 as a catalyst under microwave-assisted conditions. This method is simple, easy to work up, inexpensive, with a broad substrate scope and short reaction times. The reaction provides 1,2-dihydroquinolines (19 examples) in good yields (34-97%

  在微波辅助条件下，使用催化量的市售 Bi(OTf)3 作为催化剂，由取代的苯胺和丙酮酸甲酯合成了取代的 1,2-二氢喹啉。该方法简单、易于操作、价格低廉、底物范围广、反应时间短。该反应以良好的产率（34-97% 的产率）提供了 1,2-二氢喹啉（19 个实施例）。
• Regioselective Synthesis of 1,2-Dihydroquinolines by a Solvent-Free MgBr₂-Catalyzed Multicomponent Reaction
  作者：Rsuini U. Gutiérrez、Hans C. Correa、Rafael Bautista、José Luis Vargas、Alberto V. Jerezano、Francisco Delgado、Joaquín Tamariz

  DOI：10.1021/jo400973g

  日期：2013.10.4

  two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of

  描述了通过苯胺和两个酮之间的多组分反应的1，2-二氢喹啉的高效和区域选择性合成。该反应用溴化镁催化，并在无溶剂的条件下进行。当通过使用3-取代的苯胺和非对称取代的酮进行反应时，在四种预期的区域异构体中主要发现单一产物。对包括环酮在内的各种苯胺和酮进行了评估，从而提供了一系列具有不同取代方式的1,2-二氢喹啉。讨论了该机制的研究。有证据表明，在环化杂环之前，由于苯胺和一种酮之间的反应而导致亚胺的原位形成。
• Green synthesis of TiO ₂ nanoparticles as an efficient heterogeneous catalyst with high reusability for synthesis of 1,2‐dihydroquinoline derivatives
  作者：Mahmoud Abd El Aleem Ali Ali El‐Remaily、Ahmed M. Abu‐Dief、O. Elhady

  DOI：10.1002/aoc.5005

  日期：2019.8

  TiO2 NPs synthesis using agricultural waste at lower applied temperature. Characterization of the extracted TiO2 NPs was confirmed by XRD, SEM, EDAX, TEM, HR‐TEM, SAED, and FT‐IR, respectively. The catalytic activity of TiO2 NPs was investigated in synthesis of 1,2‐dihydroquinoline derivatives with excellent yields and low cost. Purification of the synthesized 1,2‐dihydroquinoline derivatives carried

  纳米材料由于其在纳米尺度上的行为而得到广泛的应用。使用印em叶提取物合成了TiO 2纳米颗粒（TiO 2 NPs）。这是在较低的应用温度下使用农业废料合成TiO 2 NP的简单，快速，环保，便宜和绿色的工具。分别通过XRD，SEM，EDAX，TEM，HR‐TEM，SAE和FT‐IR证实了提取的TiO 2 NP的表征。在合成1,2-二氢喹啉衍生物中，以优异的产率和低成本研究了TiO 2 NPs的催化活性。合成的1,2-二氢喹啉衍生物的纯化可通过简单的非色谱方法进行。
• Brønsted acid (HNO3)-catalyzed tandem reaction of α-ketoesters and arylamines: efficient synthesis of 1,2-dihydroquinoline derivatives
  作者：Xiao-Yu Hu、Ji-Chen Zhang、Wei Wei、Jian-Xin Ji

  DOI：10.1016/j.tetlet.2011.03.134

  日期：2011.6

  A simple and convenient Brønsted acid (HNO3)-catalyzed tandem reaction of α-ketoesters with primary or secondary aromatic amines for the synthesis of polysubstituted 1,2-dihydroquinolines has been developed via a tandem process, which has the advantages of ready availability of catalyst, operation simplicity, atom efficiency as well as low toxicity. In particular, tricyclic dihydroquinolines, generally

  通过串联方法开发了一种简单便捷的布朗斯台德酸（HNO 3）催化α-酮酸酯与伯或仲芳族胺的串联反应，用于合成多取代1,2-二氢喹啉的方法，该方法具有易于获得的优点催化剂，操作简便，原子效率高，毒性低。特别地，通常用多方法制备的三环二氢喹啉也可以在该一锅法中构建。