N,N-(pyromellitoyl)-bis-L-phenylalanine | 144443-37-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: N,N-(pyromellitoyl)-bis-L-phenylalanine
• 英文别名: (2S)-2-[2-[(1S)-1-carboxy-2-phenylethyl]-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-6-yl]-3-phenylpropanoic acid
• CAS: 144443-37-8
• 化学式: C₂₈H₂₀N₂O₈
• 分子量: 512.475
• InChiKey: YCWVHQLWDWGSQU-VXKWHMMOSA-N

物化性质

• 熔点：
  292-294 °C
• 沸点：
  784.0±60.0 °C(Predicted)
• 密度：
  1.550±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 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-(pyromellitoyl)-bis-L-phenylalanine 在 氯化亚砜 作用下， 生成 (2S)-2-[2-[(2S)-1-chloro-1-oxo-3-phenylpropan-2-yl]-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-6-yl]-3-phenylpropanoyl chloride
  参考文献：
  名称：

  Insertion of novel optically active poly(amide-imide) chains containing pyromellitoyl-bis-l-phenylalanine linkages into the nanolayered silicates modified with l-tyrosine through solution intercalation

  摘要：

  In the present investigation, for the first time, functional optically active poly(amide-imide) (PAI)/organonanosilica bionanocomposite films were successfully fabricated through solution intercalation technique. At the start, Cloisite Na+ and protonated form of L-tyrosine amino acid were used for the preparation of the novel chiral organoclay via ion-exchange reaction. Then, PAI containing phenylalanine amino acid was synthesized via solution polycondensation of N,N'-(pyromellitoyl)-bis-phenylalanine diacid chloride (5) with 4,4'-diaminodiphenylsulfone (6). This polymer was end-capped with amine end groups near the completion of the reaction to interact chemically with organoclay. Finally, PAI/organ-nanosilica bionanocomposites films containing 5, 10 and 15% of organoclay were prepared via solution intercalation method through blending of organoclay with the PAI solution. The nanostructures and properties of the PAI/organoclay hybrids were investigated using Fourier transform infrared spectroscopy, X-ray diffraction (XRD), scanning electron microscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM) and thermogravimetry analysis (TGA) techniques. XRD, FE-SEM and TEM results revealed the formation of exfoliated and intercalated organoclay platelets in the PAI matrix. TGA results indicated that the addition of organoclay into the PAI matrix increases in the thermal decomposition temperatures of the resulted bionanocomposites. The transparency of the nanocomposite films decreased gradually by the addition of organoclay, and the films became semitransparent as well as brittle at high loading of organoclay. Mechanical data indicated improvement in the tensile strength and modulus with organoclay loading. The film containing a 10 wt.%. of organoclay had a tensile strength of the order of 85.24 MPa relative to the 67.52 MPa of the pure PAL (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.04.013
• 作为产物：
  描述：

  L-苯丙氨酸 在 溶剂黄146 作用下， 生成 N,N-(pyromellitoyl)-bis-L-phenylalanine
  参考文献：
  名称：

  Insertion of novel optically active poly(amide-imide) chains containing pyromellitoyl-bis-l-phenylalanine linkages into the nanolayered silicates modified with l-tyrosine through solution intercalation

  摘要：

  In the present investigation, for the first time, functional optically active poly(amide-imide) (PAI)/organonanosilica bionanocomposite films were successfully fabricated through solution intercalation technique. At the start, Cloisite Na+ and protonated form of L-tyrosine amino acid were used for the preparation of the novel chiral organoclay via ion-exchange reaction. Then, PAI containing phenylalanine amino acid was synthesized via solution polycondensation of N,N'-(pyromellitoyl)-bis-phenylalanine diacid chloride (5) with 4,4'-diaminodiphenylsulfone (6). This polymer was end-capped with amine end groups near the completion of the reaction to interact chemically with organoclay. Finally, PAI/organ-nanosilica bionanocomposites films containing 5, 10 and 15% of organoclay were prepared via solution intercalation method through blending of organoclay with the PAI solution. The nanostructures and properties of the PAI/organoclay hybrids were investigated using Fourier transform infrared spectroscopy, X-ray diffraction (XRD), scanning electron microscopy, field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM) and thermogravimetry analysis (TGA) techniques. XRD, FE-SEM and TEM results revealed the formation of exfoliated and intercalated organoclay platelets in the PAI matrix. TGA results indicated that the addition of organoclay into the PAI matrix increases in the thermal decomposition temperatures of the resulted bionanocomposites. The transparency of the nanocomposite films decreased gradually by the addition of organoclay, and the films became semitransparent as well as brittle at high loading of organoclay. Mechanical data indicated improvement in the tensile strength and modulus with organoclay loading. The film containing a 10 wt.%. of organoclay had a tensile strength of the order of 85.24 MPa relative to the 67.52 MPa of the pure PAL (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.04.013

文献信息

• Highly efficient one-step microwave-assisted synthesis of structurally diverse bis-substituted α-amino acid derived diimides
  作者：Marcin Konopka、Grzegorz Markiewicz、Artur R. Stefankiewicz

  DOI：10.1039/c8ra05835k

  日期：——

  We report herein a facile and widely applicable microwave-assisted protocol for the synthesis of symmetrical diimides based on three structurally distinct aromatic dianhydrides: pyromellitic (PMA), biphenyl-tetracarboxylic acid (BPDA) and benzophenone-tetracarboxylic (BTDA) and five natural amino acids (Phe, Tyr, Ile, Lys, Cys). Fifteen symmetrical diimides with different structural characteristics

  我们在此报告了一种简便且广泛适用的微波辅助方案，用于合成基于三种结构不同的芳族二酐的对称二酰亚胺：均苯四甲酸 (PMA)、联苯四羧酸 (BPDA) 和二苯甲酮四羧酸 (BTDA) 和五种天然氨基酸(Phe、Tyr、Ile、Lys、Cys)。十五种具有不同结构特征、含有多种官能团的对称二酰亚胺可以高产率和大规模生产。
• Studies on syntheses and morphology characteristic of chiral novel poly(ester-imide)/TiO2 bionanocomposites derived from l-phenylalanine based diacid
  作者：Shadpour Mallakpour、Samaneh Soltanian

  DOI：10.1016/j.polymer.2010.09.063

  日期：2010.10

  synthesized from the polymerization reaction of N,N′-(pyromellitoyl)-bis-l-phenylalanine diacid with 4,4′-thiobis(2-tert-butyl-5-methylphenol) using tosyl chloride, pyridine and N,N-dimethyl formamide as a condensing agent. The obtained polymer and inorganic metal oxide bionanocomposites composed of poly(ester-imide)/titanium dioxide were synthesized through ultrasonic irradiation. The formation of PEI was

  在这项研究中，由N，N'-（均苯四甲酰基）-双-1-苯丙氨酸二酸与4,4'-硫代双（2-叔丁基）的聚合反应合成了一种新型的旋光性聚（酯酰亚胺）（PEI）。-丁基-5-甲基苯酚），使用甲苯磺酰氯，吡啶和N，N-二甲基甲酰胺作为缩合剂。通过超声辐射合成了由聚（酯-酰亚胺）/二氧化钛组成的聚合物和无机金属氧化物的纳米复合材料。PEI的形成已由1确认1 H NMR，傅立叶变换红外光谱（FT-IR），比旋光度和元素分析。通过FT-IR，粉末X射线衍射（XRD），原子力显微镜（AFM），扫描电子显微镜（SEM），场发射扫描电子显微镜（FE-SEM），透射电子显微镜（TEM）对所得的纳米复合材料进行表征TEM，SEM和FE-SEM结果表明，纳米颗粒均匀地分散在PEI基体中，TGA证实了TiO 2纳米颗粒的存在提高了纳米复合材料的热稳定性。
• 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。
• 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。
• Dirhodium Coordination Polymers for Asymmetric Cyclopropanation of Diazooxindoles with Olefins: Synthesis and Spectroscopic Analysis
  作者：Zhenzhong Li、Lorenz Rösler、Kevin Herr、Martin Brodrecht、Hergen Breitzke、Kathrin Hofmann、Hans‐Heinrich Limbach、Torsten Gutmann、Gerd Buntkowsky

  DOI：10.1002/cplu.202000421

  日期：2020.8

  formation of the coordination polymers. 19F MAS NMR was utilized to investigate the remaining TFA groups in the obtained coordination polymers, and demonstrated near‐quantitative ligand exchange. DR‐UV‐vis and XPS confirm the oxidation state of the Rh center and that the Rh‐single bond in the dirhodium node is maintained in the synthesis of Rh2‐L1 and Rh2‐L2. Both coordination polymers exhibit excellent catalytic

  一种简便方法是报道了二铑配位聚合物的[Rh的制备2（L1）2 ] Ñ（铑2 -L 1）和铑[Rh 2（L2）2 ] Ñ（铑2 -L 2; L 1 = N，N” - （pyromellitoyl） -双-大号-苯丙氨酸二酸阴离子，L2 =双-N，N'-（L-通过配体交换从手性二羧酸苯丙）萘1,4,5,8-四羧酸二酰亚胺）。包括FTIR，XPS和1 H→ 13 C CP MAS NMR光谱在内的多种技术揭示了配位聚合物的形成。19F MAS NMR用于研究所得配位聚合物中的其余TFA基团，并证明了近定量的配体交换。DR-UV-vis和XPS证实了Rh中心的氧化状态，并且在Rh 2 -L1和Rh 2 -L2的合成过程中，保持了ho节点中的Rh单键。两种配位聚合物在苯乙烯和重氮恶唑之间的不对称环丙烷化反应中均表现出优异的催化性能。催化剂可以容易地再循环和再利用，而不会显着降低其催化效率。