N,N'-pyromelliticdiimido-di-L-alanine | 136458-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N'-pyromelliticdiimido-di-L-alanine
• 英文别名: N,N-(pyromellitoyl)-bis-L-alanine；N,N'-(pyromellitoyl)-bis-L-alanine diacid；(2S)-2-[2-[(1S)-1-carboxyethyl]-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-6-yl]propanoic acid
• CAS: 136458-21-4
• 化学式: C₁₆H₁₂N₂O₈
• 分子量: 360.28
• InChiKey: NZOYHSWKNKZJMQ-WDSKDSINSA-N

物化性质

• 熔点：
  291-293 °C
• 沸点：
  670.1±50.0 °C(Predicted)
• 密度：
  1.722±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-pyromelliticdiimido-di-L-alanine 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 2.0h， 以96%的产率得到N,N'-(pyromellitoyl)-bis-L-alanine diacyl chloride
  参考文献：
  名称：

  含l-丙氨酸的光学活性聚（酯酰亚胺）的微波辅助合成与表征

  摘要：

  均苯四甲酸二酐（1）与L-丙氨酸（2）反应，得到[ N，N' -（均苯四甲酰基）-双-1-丙氨酸二酸]（3）。通过与亚硫酰氯反应，将该化合物（3）转化为N，N' -（均苯四甲酰基）-双-1-丙氨酸二酰氯（4）。该二酰氯（4）与聚乙二醇二醇（PEG-200）和/或三种合成的芳香族二醇的微波辅助缩合反应可在实验室微波炉（里程碑）中提供一系列新的PEI和Co-PEI。所得的聚合物和共聚物的固有粘度为0.31-0.53 dl g -1。这些聚合物具有光学活性，热稳定性，可溶于极性非质子溶剂，例如DMF，DMSO，NMP，DMAc和硫酸。上述所有聚合物均通过IR光谱，1 H NMR光谱，元素分析，比旋光度和热分析进行了全面表征。已经报道了这些旋光性PEI和Co-PEI的一些结构特征和物理性质。

  DOI：

  10.1007/s00726-009-0336-6
• 作为产物：
  描述：

  均苯四甲酸二酐 在 溶剂黄146 作用下， 生成 N,N'-pyromelliticdiimido-di-L-alanine
  参考文献：
  名称：

  Novel nanostructure amino acid-based poly(amide–imide)s enclosing benzimidazole pendant group in green medium: fabrication and characterization

  摘要：

  In the present work, several novel optically active nanostructure poly(amide-imide)s (PAI)s were synthesized via step-growth polymerization reaction of chiral diacids based on pyromellitic dianhydride-derived dicarboxylic acids containing different natural amino acids such as l-alanine, S-valine, l-leucine, l-isoleucine, l-methionine, and l-phenylalanine with 2-(3,5-diaminophenyl)-benzimidazole under green conditions using molten tetrabutylammonium bromide. The new optically active PAIs were achieved in good yields and moderate inherent viscosity up to 0.41 dL/g. The synthesized polymers were characterized with FT-IR, H-1-NMR, X-ray diffraction, field emission scanning electron microscopy (FE-SEM), elemental and thermogravimetric analysis (TGA) techniques. These polymers show high solubility in organic polar solvents due to the presence of amino acid and benzimidazole pendant group at room temperature. FE-SEM results show that, these chiral nanostructured PAIs have spherical shapes and the particle size is around 20-80 nm. On the basis of TGA data, such PAIs are thermally stable and can be classified as self-extinguishing polymers. In addition due to the existence of amino acids in the polymer backbones, these macromolecules are not only optically active but also could be biodegradable and thus may well be classified under environmentally friendly materials.

  DOI：

  10.1007/s00726-012-1236-8

文献信息

• Synthesis, characterization and in vitro antimicrobial and biodegradability study of pseudo-poly(amino acid)s derived from N,N′-(pyromellitoyl)-bis-l-tyrosine dimethyl ester as a chiral bioactive diphenolic monomer
  作者：Shadpour Mallakpour、Farhang Tirgir、Mohammad R. Sabzalian

  DOI：10.1007/s00726-010-0686-0

  日期：2011.2

  N,N′-(pyromellitoyl)-bis-l-tyrosine dimethyl ester (7) as a chiral bioactive diphenolic monomer was prepared in three steps. The aim of this work was to obtain novel optically and biologically active pseudo-poly(amino acid)s (PAA)s that are more soluble in common organic solvents while maintaining their high thermal stability. Thus, several new, highly soluble, thermally stable, optically active and

  在该研究中N， ' - （pyromellitoyl） -双-升-酪氨酸甲酯（7），为手性的生物活性在三个步骤制备双酚单体。这项工作的目的是获得新型的光学和生物活性假聚（氨基酸）（PAA），它们在普通的有机溶剂中更易溶，同时保持其高的热稳定性。因此，通过使用甲苯磺酰氯，吡啶和N，N通过直接缩聚反应，制备了几种新的，高溶解性，热稳定，光学活性和可生物降解的主链中包含不同氨基酸部分的PAA，它们具有中等分子量。′-二甲基甲酰胺作为缩合剂。用FT-IR，1 H-NMR，元素和热重分析技术对所得的新型聚合物进行表征。此外，在培养基中对双酚单体7，不同的合成二酸（3a - 3e）和获得的PAA进行了体外毒性和生物降解性研究，结果表明合成的化合物和由其衍生的聚合物具有生物活性和可生物降解性。在自然环境下。
• Synthesis of novel nanostructured chiral poly(amide-imide)s containing dopamine and natural amino acids
  作者：Shadpour Mallakpour、Amin Zadehnazari

  DOI：10.1007/s12039-012-0351-0

  日期：2013.1

  Four new thermally stable and optically active poly(amide-imide)s (PAI)s with good inherent viscosities were synthesized from the direct polycondensation reaction of N,N′-(pyromellitoyl)-bis-L-α-amino acids with 3,5-diamino-N-(3,4-dihydroxy-phen-ethyl)benzamide in a medium consisting of a molten salt, tetrabutylammonium bromide, and triphenyl phosphite as the activator. The polymerization reactions

  通过N，N ' -（均苯四甲酰基）-双-L - α-氨基酸与3，N，N '的直接缩聚反应合成了四种具有良好固有粘度的新型热稳定且光学活性的聚（酰胺-酰亚胺）（PAI）。在由熔融盐，四丁基溴化铵和亚磷酸三苯酯作为活化剂组成的介质中的5-二氨基-N-（3,4-二羟基-苯乙基）苯甲酰胺 聚合反应以高收率生产了一系列新型PAI，PAA在侧链中包含多巴胺链段，固有粘度在0.33至0.49 dL / g之间。所得聚合物通常通过FT-IR 1表征。1 H NMR光谱，元素分析，粉末X射线衍射，场发射扫描电子显微镜，比浓对数粘度和溶解度测试。还使用热重分析（TGA和DTG）和极限氧指数（LOI）研究了PAI的热性能和阻燃性能。通过热分析获得的数据表明这些聚合物表现出良好的热稳定性。此外，TGA的高炭收率和良好的LOI值表明所获得的聚合物能够表现出良好的阻燃性能。 通过3,5-二氨基-N-（3,4-二羟基苯
• Ultrasonic-assisted synthesis and characterization of layered double hydroxides intercalated with bioactive N,N′-(pyromellitoyl)-bis-l-α-amino acids
  作者：Shadpour Mallakpour、Mohammad Dinari、Vajiheh Behranvand

  DOI：10.1039/c3ra43645d

  日期：——

  In this study Mg/Al layered double hydroxides (LDHs) and organo-modified chiral LDHs were synthesized in one step under green conditions. Co-precipitation reaction of the Al(NO3)3·9H2O, Mg(NO3)2·6H2O and different biocompatible N,N-(pyromellitoyl)-bis-L-amino acids was carried out in aqueous solution in a short time by an ultrasonic technique. Field emission scanning electron microscopy and transmission electron microscopy techniques showed that the resulting products have good crystallinity and uniform morphology. The presence of the bioactive surfactants in the interlayer space of LDH was confirmed by Fourier transform infrared spectroscopy, X-ray diffraction (XRD) and thermogravimetry analysis techniques. As expected, the positions of the basal reflections in the XRD patterns of modified samples are shifted to higher d value indicating the expansion of the interlayer distance. Thermal properties were investigated by the thermogravimetric analysis technique.

  在这项研究中，镁/铝层状双氢氧化物（LDHs）和有机改性手性LDHs在绿色条件下一步合成。通过超声波技术，在水溶液中快速进行铝硝酸盐（Al(NO3)3·9H2O）、镁硝酸盐（Mg( )2·6H2O）和不同生物相容性N,N-(丙烯酰基)双-L-氨基酸的共沉淀反应。场发射扫描电子显微镜和透射电子显微镜技术表明，所得到的产品具有良好的结晶性和均匀的形态。通过傅里叶变换红外光谱、X射线衍射（XRD）和热重分析技术确认生物活性表面活性剂存在于LDH的层间空间中。如预期，改性样品的XRD图谱中的基面反射位置向较高的d值移动，表明层间距的扩大。热性能通过热重分析技术进行了研究。
• Flexible amorphous metal–organic frameworks with π Lewis acidic pore surface for selective adsorptive separations
  作者：Javier Fonseca、Sunho Choi

  DOI：10.1039/d1dt00079a

  日期：——

  new porous, dynamic and amorphous metal–organic frameworks (MOFs), NEU-3 [= Zn(PMDA)(Py)2] and NEU-4 [= Fe(PMDA)(Py)2] are disclosed. These MOFs along with NEU-1c [= Zn(BPDI)(Py)2] and NEU-2 [= Fe(BPDI)(Py)2] display an electron-deficient pore surface due to predesigned π-electron-deficient ligands. They are unique smart guest-responsive materials owing to their π Lewis acidic pore surface and presumably

  在石化工业中，轻烃（LHs）的选择性分离和挥发性有机化合物（VOCs）的吸附仍然是昂贵且复杂的科学挑战。形状选择吸附材料可以经济高效地满足这些要求。公开了两种新的多孔，动态和非晶态金属-有机骨架（MOF），即NEU-3 [= Zn（PMDA）（Py）2 ]和NEU-4 [= Fe（PMDA）（Py）2 ]。这些MOF以及NEU-1c [= Zn（BPDI）（Py）2 ]和NEU-2 [= Fe（BPDI）（Py）2由于预先设计的π电子缺陷配体，其显示出电子缺陷的孔表面。由于它们的πLewis酸性孔表面以及大概的骨架柔韧性，它们是独特的智能宾客响应材料。通过使用NEU-1c，NEU-2，NEU-3和NEU-4床可实现多种有效的吸附和吸附分离。NEU-4有望用于石化行业的进一步研究，显示出超高的苯吸附能力，识别能力，相对于类似物的苯选择性以及高稳定性和可再生性。
• Guest-Responsive Function of a Dynamic Metal-Organic Framework with a π Lewis Acidic Pore Surface
  作者：Biplab Joarder、Soumya Mukherjee、Abhijeet K. Chaudhari、Aamod V. Desai、Biplab Manna、Sujit K. Ghosh

  DOI：10.1002/chem.201402855

  日期：2014.11.17

  A 3D dynamic coordination framework with an electron‐deficient pore surface has been synthesized by using ZnII (having a variable coordination number) and a predesigned flexible π‐electron‐deficient core‐based ligand, exhibiting chemical separations based on pore surface functionalization (π Lewis acidic pore surfaces and open metal sites) and framework flexibility, giving rise to a unique smart guest‐responsive

  通过使用Zn II（具有可变的配位数）和预先设计的基于π电子缺铁芯的柔性配体，合成了具有缺电子孔表面的3D动态配位框架，并基于孔表面功能化（π Lewis酸性孔表面和开放的金属部位）和框架的柔韧性，产生了一种独特的智能宾客响应材料。