N-(4-carboxyphenyl)maleamic acid | 5432-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-carboxyphenyl)maleamic acid
• 英文别名: Mal-Pab；4-maleamidobenzoic acid；4'-carboxymaleanilic acid；N-(4-carboxyphenyl)maleimic acid；4–[(2Z)–3–carboxy–1–oxo–2–propen–1–yl]aminobenzoic acid；4-[[(2Z)-3-carboxy-1-oxo-2-propen-1-yl]amino]benzoic acid；(Z)-4-[(4-carboxyphenyl)amino]-4-oxobut-2-enoic acid；(Z)-3-(4-carboxy-phenylcarbamoyl)-acrylic acid；Maleinsaeure-mono-4-carboxy-anilid；p-CPMA；(Z)-4-(3-carboxyacrylamido)benzoic acid；4-[[(Z)-3-carboxyprop-2-enoyl]amino]benzoic acid
• CAS: 5432-04-2
• 化学式: C₁₁H₉NO₅
• 分子量: 235.196
• InChiKey: KDCFOKATFSLHQS-WAYWQWQTSA-N

物化性质

• 熔点：
  285 °C (decomp)
• 沸点：
  564.7±50.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-(4-carboxyphenyl)maleamic acid 在 sodium azide 、 sodium acetate 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 N-(4-(叠氮羰基)苯基)马来酰亚胺
  参考文献：
  名称：

  Selectivity Control by Chemical Modification of the Recognition Sites in Two-Point Binding Molecularly Imprinted Polymer

  摘要：

  We demonstrated the possibility of modifying the selectivity of a two-point binding imprinted polymer by chemical modification of the binding sites inside the cavities. We used a thermally reversible bond for the preparation of the monomer-template complex, which allowed us to remove the template easily by means of a simple thermal reaction and to simultaneously introduce various functional groups into the cavity. A phenylmaleimide having an azidocarbonyl group was reacted with diethylstilbestrol (DES, template) to yield a monomer, where the template was linked to two polymerizable maleimido groups via a thermally reversible urethane bond. The polymerization of the monomer was carried out in the presence of ethylene glycol dimethacrylate (EGDMA) by the initiation with 2,2-azobis(isobutyronitrile) (AIBN) at 54 degreesC in DMF. The polymers were refluxed in 1,4-dioxane in the presence of a nucleophile such as water, methanol, or aniline. In this extraction step, the template molecules were removed from the polymer matrix, and simultaneously the isocyanato groups, which were generated by the thermal cleavage of the urethane bond, were converted to amino, urethane, or urea groups through their reaction with water, methanol, or aniline, respectively. The specific recognition ability of the imprinted polymers for the template and its structural analogues was dependent on the space between the two binding points as well as on the nature of the functional group. This method is especially propitious for developing artificial receptors for molecules lacking strongly interactive groups.

  DOI：

  10.1021/ma0496089
• 作为产物：
  描述：

  马来酸酐 、 对氨基苯甲酸 以 甲苯 为溶剂， 反应 3.0h， 生成 N-(4-carboxyphenyl)maleamic acid
  参考文献：
  名称：

  使用酸性离子液体作为催化剂合成马来酰亚胺衍生物的简便且经济的方法

  摘要：

  使用布朗斯台德酸性室温离子液体（RTIL）作为催化剂，从相应的马来酰胺酸中以高收率和高纯度合成了七个马来酰亚胺衍生物。仅通过de析和除去溶剂即可获得产物，这表明该方法优于常规方法，在常规方法中，使用强有机/无机酸作为催化剂，并且对烃类进行了复杂的后处理程序。使用产物的分离和纯化。

  DOI：

  10.1016/j.tetlet.2012.06.025
• 作为试剂：
  描述：

  马来酸酐 、 对氨基苯甲酸 、 水 在 氮气 、 N-(4-carboxyphenyl)maleamic acid 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以to obtain pure N-(4-carboxyphenyl)maleamic acid的产率得到N-(4-carboxyphenyl)maleamic acid
  参考文献：
  名称：

  Compounds with electron donor and electron acceptor functionality

  摘要：

  同时含有电子供体和电子受体功能的化合物适用于粘合剂。电子供体基团是连接到芳香环上的碳到碳双键，并与环中的不饱和度共轭的基团。电子受体基团是马来酰亚胺，丙烯酸酯，富马酸或马来酸。

  公开号：

  US06300456B1

文献信息

• The synthesis of (<i>Z</i>)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes
  作者：Koray Oktay、Leyla Polat Köse、Kıvılcım Şendil、Mehmet Serdar Gültekin、İlhami Gülçin、Claudiu T. Supuran

  DOI：10.3109/14756366.2015.1071808

  日期：2016.11.1

  spectroscopy. Carbonic anhydrase is a metalloenzyme involved in many crucial physiologic processes as it catalyzes a simple but fundamental reaction, the reversible hydration of carbon dioxide to bicarbonate and protons. Significant results were obtained by evaluating the enzyme inhibitory activities of these derivatives against human carbonic anhydrase hCA I and II isoenzymes (hCA I and II). Butenoic

  提出了具有可用于合成多个活性分子的结构特征的（Z）-4-氧代-4-（芳基氨基）丁-2-烯酸（4）衍生物的合成。按照文献程序并在反应结束时合成一些丁烯酸衍生物（4a，4c，4e，4i，4j，4k）。另外，通过（1）H-NMR，（13）C-NMR和IR光谱确定所有合成衍生物（4a-4m）的结构。碳酸酐酶是一种涉及许多关键生理过程的金属酶，因为它催化一个简单但基本的反应，即二氧化碳可逆地水合成碳酸氢根和质子。通过评估这些衍生物对人碳酸酐酶hCA I和II同功酶（hCA I和II）的酶抑制活性，获得了重要的结果。
• Compounds containing a michael-acceptor, especially maleimide or maleic
  申请人：Vanguard Medica Limited

  公开号：US05877204A1

  公开（公告）日：1999-03-02

  The present invention relates to compounds which are useful as sunscreens. The compounds persist on the skin for much longer than conventional sunscreens because they comprise a Michael acceptor linked directly or indirectly to a chromophore. The Michael acceptor is capable of undergoing a conjugate addition reaction with thiol groups present in cysteine residues of keratin and thus the compound is chemically bound to the skin and will not be removed by immersion in water.

  本发明涉及作为防晒剂有用的化合物。这些化合物在皮肤上持续时间比传统防晒剂长得多，因为它们包含一个与色团直接或间接连接的迈克尔受体。迈克尔受体能够与角蛋白半胱氨酸残基中存在的巯基发生共轭加成反应，因此该化合物与皮肤化学结合，不会被水浸泡而去除。
• Synthesis of Diels–Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines
  作者：J. Alberto Guevara-Salazar、Delia Quintana-Zavala、Hugo A. Jiménez-Vázquez、José Trujillo-Ferrara

  DOI：10.1007/s00706-011-0515-5

  日期：2011.8

  AbstractWe have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the absence of catalysts. According to additional experiments, the MCR takes place by sequential formation of N-arylmaleamic acids from the aminobenzoic

  摘要我们在不存在催化剂的情况下，通过氨基苯甲酸或氨基苯甲酸酯，马来酸酐和异戊二烯之间的多组分反应（MCR），对一些六氢异吲哚基苯甲酸及其相应的乙酯进行了合成和表征。根据其他实验，MCR是通过依次从氨基苯甲酸或氨基苯甲酸酯和顺丁烯二酸酐，酸和异戊二烯的Diels–Alder加合物，最后是酰亚胺形成N-芳基马来酰胺酸而发生的。加合物的1 H NMR数据（耦合常数）表明，相应的环己烯环的优选构型是顺式-船，由密度泛函理论（DFT）构象分析和相应构象异构体自旋-自旋耦合常数的DFT计算所支持的事实。我们的MCR合成方法在其他加合物的合成中成功进行了测试，其中使用了环戊二烯和其他苯胺。 图形概要
• Novel Antimicrobial Organic Thermal Stabilizer and Co-Stabilizer for Rigid PVC
  作者：Mona M. Fahmy、Riham R. Mohamed、Nadia A. Mohamed

  DOI：10.3390/molecules17077927

  日期：——

  Biologically active N-benzoyl-4-(N-maleimido)-phenylhydrazide (BMPH) was synthesized and its structure was confirmed by elemental analysis and various spectral tools. It was examined as a thermal stabilizer and co-stabilizer for rigid poly (vinyl chloride) at 180 °C in air. Blending BMPH with reference samples in different ratios greatly lengthens the thermal stability value and improves the extent of discoloration of PVC. TGA confirmed the improved stability of PVC in presence of the investigated organic stabilizer. GPC measurements were done to investigate the changes occurred in the molecular masses of the degraded samples of blank PVC and PVC in presence of the novel stabilizer. BMPH showed good antimicrobial activity towards two kinds of bacteria and two kinds of fungi.

  生物活性N-苯甲酰-4-(N-马来酰亚胺)-苯基肼(BMPH)被合成，并通过元素分析和多种光谱工具确认其结构。在180°C的空气中，BMPH被检测为硬质聚氯乙烯的热稳定剂和共稳定剂。以不同比例将BMPH与参比样品混合，大大延长了热稳定性值，并改善了PVC的褪色程度。热重分析(TGA)证实了加入研究的有机稳定剂后PVC稳定性的提高。进行了凝胶渗透色谱(GPC)测量，以研究空白PVC和加入新型稳定剂的PVC的降解样品中分子质量的变化。BMPH对两种细菌和两种真菌表现出良好的抗菌活性。
• Solvent free preparation of N-substituted maleanilic acid
  作者：H. Saedi

  DOI：10.4314/bcse.v27i1.15

  日期：——

  Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4-bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) were prepared by solvent free reaction between maleic anhydride and a 4-carboxy, 4-bromo, 4-hydroxy, 3-hydroxy, 4-chloro and 4-methyl aniline derivatives in good to excellent yield. FT-IR, 1H-NMR and 13C-NMR spectra revealed the confirmation of these compounds in good agreement.

  六种N-马来酰胺酸，即N-(4-羧基)马来酰胺酸（CAMAA）、N-(4-溴基)马来酰胺酸（BMAA）、N-(4-羟基)马来酰胺酸（HMAA）、N-(3-羟基)马来酰胺酸（mHMAA）、N-(4-氯基)马来酰胺酸（CMAA）和N-(4-甲基)马来酰胺酸（MMAA），均通过无溶剂反应由马来酸酐和4-羧基、4-溴基、4-羟基、3-羟基、4-氯基及4-甲基苯胺衍生物制备，产率优良至极佳。FT-IR、1H-NMR和13C-NMR光谱分析证实了这些化合物的结构，数据良好一致。