3-(2-nitrophenyl)-2-carboxy-2-propenoic acid | 103582-31-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-nitrophenyl)-2-carboxy-2-propenoic acid
• 英文别名: 2-(4-nitrobenzylidene)malonic acid；2-(2-nitrobenzylidene)malonic acid；(2-nitro-benzylidene)-malonic acid；(2-Nitro-benzyliden)-malonsaeure；2-Nitro-benzalmalonsaeure；2-[(2-nitrophenyl)methylidene]propanedioic acid
• CAS: 103582-31-6
• 化学式: C₁₀H₇NO₆
• 分子量: 237.169
• InChiKey: PWOSYAXUKPDKHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  200-205 °C (decomp)
• 沸点：
  478.0±40.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(2-nitrophenyl)-2-carboxy-2-propenoic acid 在 溶剂黄146 、 锌 作用下， 生成 2-hydroxy-1-oxy-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Heller; Wunderlich, Chemische Berichte, 1914, vol. 47, p. 2890

  摘要：

  DOI：
• 作为产物：
  描述：

  邻硝基苯甲醛 在 哌啶 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 16.0h， 生成 3-(2-nitrophenyl)-2-carboxy-2-propenoic acid
  参考文献：
  名称：

  Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors

  摘要：

  Inhibition of TLR4 signaling is an important therapeutic strategy for intervention in the etiology of several pro-inflammatory diseases. There has been intensive research in recent years aiming to explore this strategy, and identify small molecule inhibitors of the TLR4 pathway. However, the recent failure of a number of advanced drug candidates targeting TLR4 signaling (e.g., TAK242 and Eritoran) prompted us to continue the search for novel chemical scaffolds to inhibit this critical inflammatory response pathway. Here we report the identification of a group of new TLR4 signaling inhibitors through a cell-based screening. A series of arylidene malonate analogs were synthesized and assayed in murine macrophages for their inhibitory activity against LPS-induced nitric oxide (NO) production. The lead compound 1 (NCI126224) was found to suppress LPS-induced production of nuclear factor-kappaB (NF-kappa B), tumor necrosis factor (TNF-alpha), interleukin-1 beta (IL-1 beta), and nitric oxide (NO) in the nanomolar-low micromolar range. Taken together, this study demonstrates that 1 is a promising potential therapeutic candidate for various inflammatory diseases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.022

文献信息

• Mechanismus der Eintopf-Synthese der 3-Amino-3-(o-nitrophenyl)-propionsäure
  作者：Herbert Oelschläger、Jörg Ogorka、Ingrid Kolbeck

  DOI：10.1002/ardp.19863190603

  日期：——

  Die Eintopf‐Synthese der 3‐Amino‐3‐(o‐nitrophenyl)‐propionsäure (1) aus o‐Nitrobenzaldehyd und Malonsäure in Ammoniumacetat/Eisessig erfolgt in 3 Reaktionsschritten: Kondensation, Addition und Decarboxylierung. Nebenreaktionen wurden geklärt.

  Die Eintopf-Synthese der 3-Amino-3-(o-nitrophenyl)-propionsäure (1) aus o-Nitrobenzaldehyd und Malonsäure in Ammoniumacetat/Eisessig erfolgt in 3 Reaktionsschritten: Kondensation, Addition und Decarboxylierung。Nebenreaktionen wurden geklärt。
• Competitive Formation of β-Amino Acids, Propenoic, and Ylidenemalonic Acids by the Rodionov Reaction from Malonic Acid, Aldehydes, and Ammonium Acetate in Alcoholic Medium
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、E. A. Kovaleva、O. L. Ustinova、I. B. Kozhevnikov

  DOI：10.1007/s11176-005-0377-9

  日期：2005.7

  The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered.

  在醇介质中，利用49种可获得的脂肪醛和芳香醛与丙二酸和醋酸铵进行Rodionov反应，结果形成了β-氨基酸、丙烯酸和亚甲基丙二酸。研究揭示了该反应的某些区域选择性规律。在多种研究的酮中，仅有环己酮的反应产物为β-氨基酸。在Rodionov反应条件下，6-氯-2-氟肉桂酸的异常脱氟现象被发现。
• Synthesis of 5-alkylidene-1,3-dioxane-4,6-diones, an easily accessible family of axially chiral alkenes: preparation in non-racemic form and platinum binding studies
  作者：Meritxell Casadesus、Michael P. Coogan、Li-Ling Ooi

  DOI：10.1039/b608785j

  日期：——

  A general synthetic route to 5-alkylidene-1,3-dioxane-4,6-diones, which are a family of axially chiral alkenes, is described. Conformational issues are explored and the platinum-binding properties of these species are discussed. That these alkenes exist as stable enantiomers is established by their partial kinetic resolution upon reaction with cysteine.

  该论文描述了一种合成5-亚烷基-1,3-二氧杂环己烷-4,6-二酮类化合物的通用路线,这类化合物是一类轴手性烯烃。论文探讨了构象问题,并研究了这些化合物与铂的结合性质。通过这些烯烃与半胱氨酸反应时发生部分动力学拆分,证实了它们作为稳定对映体的存在。
• Cerium immobilized carbon nitride: A proficient and recyclable catalyst to construct carbon–carbon double bonds in water
  作者：Vadivel Saravanan、Pandian Lakshmanan、Chennan Ramalingan

  DOI：10.1002/aoc.7058

  日期：2023.4

  Cerium immobilized graphitic carbon nitride (Ce-GCN) was prepared to construct carbon–carbon double bonds from heteroaromatic/homoaromatic/aliphatic carbonyl compounds and melononitriles. The catalyst was prepared using the method of co-precipitation and characterized by infrared spectroscopy (IR), scanning electron microscopy (SEM) with energy dispersive X-ray (EDX) analysis, X-ray diffraction (XRD)

  制备了铈固定化石墨碳氮化物 (Ce-GCN)，以从杂芳族/同芳族/脂肪族羰基化合物和 melononitriles 构建碳-碳双键。该催化剂采用共沉淀法制备，并通过红外光谱（IR）、扫描电子显微镜（SEM）和能量色散X射线（EDX）分析、X射线衍射（XRD）、电感耦合等离子体光发射等手段对其进行了表征。光谱法 (ICP-OES)、X 射线光电子能谱 (XPS) 和透射电子显微镜 (TEM)。使用如此制备的催化剂后，反应在环境温度下的绿色溶剂水中进行得很好。催化效率显示出良好的可重复使用性能。
• Pyridine and related aza heterocycle derivatives as cardiovascular agents
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0446604A2

  公开（公告）日：1991-09-18

  Novel pharmaceutical compounds and compositions having nitrogen containing ring systems which may be represented by the following structural formula: wherein R₁ or R₃ is a moiety of the formula: wherein R₆ is selected from either hydrogen or acetyl; R₇ is selected from 2, 3 or 4-pyridyl or 1-imidazolyl and Q is -(CH₂)n, where n is an integer from 1 to 5 and R₁ and R₂, R₂ and R₃, R₃ and R₄ or R₄ and R₅ taken together may be -CH=CH-CH=CH-. The compounds and compositions are useful as inhibitors of thromboxane synthetase and in the treatment of hypertension and arrythmia in mammals.

  具有含氮环系统的新型药物化合物和组合物，其结构式如下： 其中 R₁ 或 R₃ 是式中的分子： 其中 R₆ 选自氢或乙酰基； R₇选自2、3或4-吡啶基或1-咪唑基，Q为-(CH₂)n，其中n为1至5的整数，R₁和R₂、R₂和R₃、R₃和R₄或R₄和R₅合起来可以是-CH=CH-CH=CH-。 这些化合物和组合物可作为血栓素合成酶的抑制剂，用于治疗哺乳动物的高血压和心律失常。