dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate | 7101-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate
• 英文别名: α-(2-Methoxy-anilino)-maleinsaeuredimethylester；o-anisidino-butenedioic acid dimethyl ester；o-Anisidino-butendisaeure-dimethylester；(2-Methoxy-phenylimino)-bernsteinsaeure-dimethylester；1,4-Dimethyl 2-[(2-methoxyphenyl)amino]but-2-enedioate；dimethyl 2-(2-methoxyanilino)but-2-enedioate
• CAS: 7101-82-8
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: LVXQPSXJHNIWRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate 在 氢碘酸 、 paraffin oil 作用下， 生成 4,8-二羟基喹啉-2-甲酸
  参考文献：
  名称：

  Musajo; Minchilli, Chemische Berichte, 1941, vol. 74, p. 1839,1841

  摘要：

  DOI：
• 作为产物：
  描述：

  草酸二甲酯 生成 dimethyl 2-((2-methoxyphenyl)amino)but-2-enedioate
  参考文献：
  名称：

  DE832748

  摘要：

  公开号：

文献信息

• Microwave-Assisted Preparation of Quinolone and Quinoline Derivatives
  作者：Markus Albrecht、Olga Osetska、Toni Rantanen、Roland Fröhlich、Carsten Bolm

  DOI：10.1055/s-0029-1219565

  日期：2010.4

  Quinolinone derivatives can be obtained in microwave-assisted syntheses by reaction of aniline derivatives with acetylene dicarboxylic esters, a malonic acid diester or β-keto ester derivatives. The reaction proceeds under mild conditions in short reaction times. Two of the quinolinones were transformed into the corresponding 4-chloroquinolines either by conventional heating or in a microwave-assisted

  通过苯胺衍生物与乙炔二羧酸酯、丙二酸二酯或β-酮酯衍生物的反应，可以在微波辅助合成中获得喹啉酮衍生物。该反应在温和的条件下在很短的反应时间内进行。通过常规加热或在微波辅助反应中，两种喹啉酮被转化为相应的 4-氯喹啉。进一步的修改导致硼加合物或附聚物的形成。后者通过 X 射线晶体结构分析表征。
• Synthesis of Highly Substituted Pyrrolo[1,2‐a]quinoline‐3,5‐diones through Ag(I) Catalyzed Cyclization of 4‐Hydroxyquinolinyl‐2‐ynones
  作者：Jais Kurian、Muraleedharan K. Manheri

  DOI：10.1002/ejoc.202300894

  日期：2023.12.6

  Ag(I)-catalyzed cyclization of 4-Hydroxyquinolinyl-2-ynones afforded pyrrolo[1,2-a]quinoline-3,5-diones in excellent yields. The core of these compounds is formed by fusion of quinolone and pyrrolone moieties, and the method gives easy access to a new class of therapeutically relevant compounds for anticancer and antibacterial drug discovery efforts.

  Ag(I) 催化的 4-羟基喹啉基-2-炔酮环化以优异的产率提供吡咯并[1,2-a]喹啉-3,5-二酮。这些化合物的核心是由喹诺酮和吡咯酮部分融合形成的，该方法可以轻松获得一类新的治疗相关化合物，用于抗癌和抗菌药物的发现工作。
• Copper-Catalyzed Three-Component Cascade Michael Addition/Heck-Type Alkylation/Annulation: Accessing Fully Substituted 1,3-Dihydro-2<i>H</i>-pyrrol-2-ones
  作者：Dan Ba、Yanhui Chen、Weiwei Lv、Si Wen、Guolin Cheng

  DOI：10.1021/acs.orglett.9b03189

  日期：2019.11.1

  We report a highly efficient copper-catalyzed three-component reaction of alkylamines, acetylenedicarboxylates, and alpha-bromocarbonyls for the assembly of fully substituted 1,3-dihydro-2H-pyrrol-2-ones. A variety of alkylamines and ammonium salt are functionalized with acetylenedicarboxylates and alpha-bromocarbonyls. N-aryl enam-inoesters are also successfully alkylated with alpha-bromocarbonyls. This protocol is understood to proceed through radical Heck-type coupling of in-situ-generated bulky trisubstituted alkenes with bulky tertiary alkyl bromides, which is realized for the first time.
• Neurogenic and neuroprotective donepezil-flavonoid hybrids with sigma-1 affinity and inhibition of key enzymes in Alzheimer's disease
  作者：Martín Estrada Valencia、Clara Herrera-Arozamena、Lucía de Andrés、Concepción Pérez、José A. Morales-García、Ana Pérez-Castillo、Eva Ramos、Alejandro Romero、Dolores Viña、Matilde Yáñez、Erik Laurini、Sabrina Pricl、María Isabel Rodríguez-Franco

  DOI：10.1016/j.ejmech.2018.07.026

  日期：2018.8

  In this work we describe neurogenic and neuroprotective donepezil-flavonoid hybrids (DFHs), exhibiting nanomolar affinities for the sigma-1 receptor (sigma R-1) and inhibition of key enzymes in Alzheimer's disease (AD), such as acetylcholinesterase (AChE), 5-lipoxygenase (5-LOX), and monoamine oxidases (MAOs). In general, new compounds scavenge free radical species, are predicted to be brain-permeable, and protect neuronal cells against mitochondrial oxidative stress. N-(2-(1-Benzylpiperidin-4-yl)ethyl)-6,7-dimethoxy-4-oxo-4H-chromene-2-carboxamide (18) is highlighted due to its interesting biological profile in sigma R-1, AChE, 5-LOX, MAO-A and MAO-B. In phenotypic assays, it protects a neuronal cell line against mitochondrial oxidative stress and promotes maturation of neural stem cells into a neuronal phenotype, which could contribute to the reparation of neuronal tissues. Molecular modelling studies of 18 in AChE, 5-LOX and sigma R-1 revealed the main interactions with these proteins, which will be further exploited in the optimization of new, more efficient DFHs. (C) 2018 Elsevier Masson SAS. All rights reserved.