2-(4-甲氧基亚苄基)丙二酸 | 21405-61-8

• 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
• 中文名称: 2-(4-甲氧基亚苄基)丙二酸
• 英文名称: 2-(4-methoxybenzylidene)malonic acid
• 英文别名: 3-(4-methoxyphenyl)-2-carboxy-2-propenoic acid；2-[(4-methoxyphenyl)methylidene]propanedioic acid
• CAS: 21405-61-8
• 化学式: C₁₁H₁₀O₅
• mdl: MFCD00749498
• 分子量: 222.197
• InChiKey: QYXHQRJWUMDWGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 沸点：
  436.1±35.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基亚苄基)丙二酸 以 乙醇 为溶剂， 反应 24.0h， 以94%的产率得到反式-4-甲氧基肉桂酸
  参考文献：
  名称：

  A one-pot synthesis of 3-amino-3-arylpropionic acids

  摘要：

  3-Aminopropionic acids (beta-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these beta-amino acids. The reaction mechanism of this one-pot synthesis of beta-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00824-4
• 作为产物：
  描述：

  4-甲氧基苯亚甲基丙二酸二甲酯 在 potassium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 以54%的产率得到2-(4-甲氧基亚苄基)丙二酸
  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

• Cinétique et mécanisme de la réaction de knoevenagel dans le benzène-2
  作者：J. Guyot、A. Kergomard

  DOI：10.1016/s0040-4020(01)91880-0

  日期：1983.1

  The kinetics of the reaction of ( + )-3-methyl cyclohexanone with malononitrile were studied in benzene at 25°, in the presence of hexylamine-acetic acid mixtures. Hexylamine gives an imine with cyclohexanone in an acid-catalysed step. This imine then reacts quickly with malononitrile. A rate law of zero order in malononitrile is observed. Separate kinetic results obtained for the formation of the

  在己胺-乙酸混合物的存在下，于25°在苯中研究了（+）-3-甲基环己酮与丙二腈的反应动力学。己胺在酸催化的步骤中生成带有环己酮的亚胺。然后，该亚胺与丙二腈快速反应。丙二腈中观察到零级速率定律。亚胺形成和亚胺-丙二腈反应获得的单独动力学结果支持了该机理。如果没有乙酸，则观察到复杂的速率定律。己胺主要起碱性催化剂的作用。伯胺羧酸在Knoevenagel反应中用作催化剂，与更常用的催化剂：哌啶，β-丙氨酸，AcOH-AcONH 4相比，通常可提高收率并缩短反应时间。
• Synthesis, Characterization and Antimicrobial Activity of Novel Pharmacophores Incorporating Imidazoline-Oxazoline Scaffold
  作者：Assem Barakat、Abdullah Mohammed Al-Majid、Faisal M. Al-Qahatany、Mohammad Shahidul Islam、Mohamed H.M. Al-Agamy

  DOI：10.5012/bkcs.2014.35.2.562

  日期：2014.2.20

  In this work, synthesis, characterization and antimicrobial activity of series of imidazolines-oxazolines scaffolds 5a-f and 10a-d have been investigated. All the imidazolines-oxazolines derivatives were prepared from acid derivatives 1 and 6a-c, and enantiomerically pure (S)-2-amino-3-methyl-1-butanol in four steps with excellent optical purity. The structures of all newly synthesized compounds have been elucidated by $^1H$, $^13}C$ NMR, GCMS, and IR spectrometry. Their purity was confirmed using elemental analysis. Some newly synthesized compounds were examined to in-vitro antimicrobial activity. Among the prepared products 10d was found to exhibits the most active against all tested bacteria and fungi with minimal inhibitory concentration (MIC) ranged between 21.9 and $42.6\mu}g/mL$.

  在本研究中，合成、表征及一系列咪唑啉-噁唑啉骨架5a-f和10a-d的抗微生物活性进行了探讨。所有咪唑啉-噁唑啉衍生物均由酸类衍生物1和6a-c以及对映体纯净的(S)-2-氨基-3-甲基-1-丁醇经过四步反应合成，且具有极好的光学纯度。所有新合成化合物的结构通过^1H NMR、^13C NMR、GCMS和IR光谱进行了解释。它们的纯度通过元素分析得到确认。部分新合成的化合物进行了体外抗微生物活性测试。在所制备的产品中，10d被发现对所有测试的细菌和真菌具有最高的活性，最小抑菌浓度（MIC）范围为21.9至42.6 μg/mL。
• Cu(I) catalysed cyclopropanation of olefins: Stereoselectivity studies with Arylid-Box and Isbut-Box ligands
  作者：Anthony J. Burke、Elisabete da Palma Carreiro、Serghei Chercheja、Nuno M.M. Moura、J.P. Prates Ramalho、Ana Isabel Rodrigues、Carla I.M. dos Santos

  DOI：10.1016/j.jorganchem.2007.06.068

  日期：2007.10

  bench stable solid that proved to be more efficient than the catalyst prepared in situ. Cu(I) pre-catalysts were used for the first time in the CAP reaction with the Isbut-Box ligands 13a and 13b and, although, the e.e.s were better for ligand 13a using these pre-catalysts, in the case of ligand 11b this was not the case. Spectroscopic studies (UV–Vis and 1H NMR) were carried out to gain an insight into

  在寻找用于高度立体选择性反应的新配体的过程中，我们测试了各种丙二酸衍生的手性非外消旋伪-C 2对称双-恶唑啉，在催化不对称反应中含有亚芳基桥单元（并适当称为Arylid-Box）苯乙烯和重氮乙酸乙酯的环丙烷化（CAP）反应仅使用1-2 mol％的Cu（I）预催化剂。获得了一些非常好的ee（高达86％）。可以分离出作为工作台稳定的固体存在的10a '-[Cu（CH 3 CN）4 ] PF 6，事实证明它比原位制备的催化剂更有效。铜（I）预催化剂用于与Isbut盒配体的CAP反应首次13A和13B，虽然，所述EES较好为配体13A使用这些预催化剂，配体的情况下，11B这事实并非如此。进行了光谱研究（UV-Vis和1 H NMR）以了解工作中催化物质的性质，以便可以优化条件以提供更好的结果。进行了一些理论研究，试图解释使用Evans的叔-Box-Cu（I）配合物获得的更好的对映选择性。
• Stabilization of iodine biocides
  申请人：Uhr Hermann

  公开号：US20090036555A1

  公开（公告）日：2009-02-05

  2-(2-Hydroxyphenyl)benzotriazoles are outstandingly suitable for stabilizing iodine-containing biocides in industrial materials, more particularly in paints based on alkyd resin.

  2-(2-羟基苯基)苯并三唑在工业材料中稳定含碘生物杀菌剂方面特别适用，尤其是在基于醇酸树脂的油性漆中。
• Microwave Enhanced Knoevenagel Condensation of Malonic Acid on Basic Alumina
  作者：Pan-Suk Kwon、Young-Mee Kim、Chul-Joong Kang、Tae-Woo Kwon、Sung-Kee Chung、Young-Tae Chang

  DOI：10.1080/00397919708005456

  日期：1997.12

  Abstract: An improved Knoevenagel condensation of malonic acid and aldehydes can be achieved by microwave irradiation over alumina. A number of diacids were prepared in good yields in very short reaction times.

  摘要：通过微波辐射氧化铝可以实现丙二酸和醛的改进的 Knoevenagel 缩合。在很短的反应时间内以良好的收率制备了许多二酸。