2,5-piperazinedione-1,4-diacetic acid | 77752-64-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,5-piperazinedione-1,4-diacetic acid
• 英文别名: 1,4-di(carboxymethyl)-2,5-diketopiperazine；2,2'-(2,5-Dioxopiperazine-1,4-diyl)diacetic acid；2-[4-(carboxymethyl)-2,5-dioxopiperazin-1-yl]acetic acid
• CAS: 77752-64-8
• 化学式: C₈H₁₀N₂O₆
• 分子量: 230.177
• InChiKey: VRDOHMYPSMRJQK-UHFFFAOYSA-N

物化性质

• 沸点：
  688.0±55.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-piperazinedione-1,4-diacetic acid 在 phosphorus(III) oxide 、 三氟甲磺酸 、 水 作用下， 反应 18.0h， 以89.4%的产率得到草甘膦
  参考文献：
  名称：

  [EN] METHOD FOR THE SYNTHESIS OF N-(PHOSPHONOMETHYL)GLYCINE
  [FR] PROCÉDÉ DE SYNTHÈSE DE N- (PHOSPHONOMÉTHYL)GLYCINE

  摘要：

  本发明涉及一种合成N-(磷酸甲基)甘氨酸或其盐、磷酸酯或磷酸酯盐衍生物的新方法，包括以下步骤：a)形成反应混合物，其中包括酸催化剂、N,N'-双(羧甲基)-2,5-二酮哌嗪和含有一个或多个P-O-P酐基团的化合物，其中该酐基团包括一个P原子在氧化态(+111)，另一个P原子在氧化态(+111)或(+V)，以形成N,N'-双(磷酸甲基)-2,5-二酮哌嗪、其脱水形式或其磷酸酯；b)水解反应混合物，以形成N-(磷酸甲基)甘氨酸或其盐、磷酸酯或磷酸酯盐衍生物中的一种。

  公开号：

  WO2014012988A1
• 作为产物：
  描述：

  亚氨基二乙酸 在 草酸 作用下， 以 水 为溶剂， 反应 120.0h， 以50%的产率得到2,5-piperazinedione-1,4-diacetic acid
  参考文献：
  名称：

  Hydrothermal reactions: From the synthesis of ligand to new lanthanide 3D-coordination polymers

  摘要：

  The organic ligand 2,5-piperazinedione-1,4-diacetic acid (H2PDA) was synthesized under hydrothermal conditions starting from the iminodiacetic acid and catalyzed by oxalic acid. The X-ray powder diffraction data indicates that the compound crystallizes in the P2(1)/c monoclinic system as reported in the literature. The ligand was also characterized by elemental analysis, magnetic nuclear resonance, infrared spectroscopy and thermogravimetric analysis. Two new coordination networks based on lanthanide ions were obtained with this ligand using hydrothermal reaction. In addition to single-crystal X-ray diffraction, the compounds were characterized by infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy and elemental analysis. Single-crystal XRD showed that the compounds are isostructural, crystallizing in P21 in monoclinic system with chemical formula [Ln(PDA)(1.3)(H2O)(1) (H2O)(3) (Ln=Gd3+ (1) and Eu-3 (2)).The luminescence properties of both compounds were studied. In the compound (1), a broad emission band was observed at 479 nm, redshifted by 70 nm in comparison of the free ligand. In (2), the typical f-f transition was observed with a maximum peak at 618 nm, related with the red emission of the europium ions. Computational methods were performed to simulate the crystal structure of (2). The theoretical calculations of the intensity parameters are in good agreement with the experimental values. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jssc.2013.09.004

文献信息

• 2-Acylaminopropanamides as growth hormone secretagogues
  申请人：ELI LILLY AND COMPANY

  公开号：EP0761220A1

  公开（公告）日：1997-03-12

  This invention provides a series of substituted propanamides which are useful in the treatment of a physiological condition which may be modulated by an increase in growth hormone. This invention also provides methods for the treatment of such physiological conditions which comprise administering a growth hormone secretagogue as described in the present invention in combination with growth hormone releasing hormone.

  这项发明提供了一系列替代丙酰胺，可用于治疗可能通过增加生长激素而调节的生理状况。该发明还提供了治疗这种生理状况的方法，包括联合使用本发明中描述的生长激素分泌促进剂和生长激素释放激素。
• Method of preparing amino carboxylic acids
  申请人：Monsanto Company

  公开号：US06153753A1

  公开（公告）日：2000-11-28

  Process for the preparation of an N-acyl amino carboxylic acid by means of a carboxymethylation reaction. In this reaction, a reaction mixture is formed which contains a base pair, carbon monoxide, hydrogen and an aldehyde with the base pair comprising a carbamoyl compound and a carboxymethylation catalyst precursor. In a preferred embodiment, the carbamoyl compound and aldehyde are selected to yield an N-acyl amino carboxylic acid which is readily converted to N-(phosphonomethyl)glycine, or a salt or ester thereof.

  通过羧甲基化反应制备N-酰基氨基羧酸的过程。在这个反应中，形成了一个反应混合物，其中包含一个碱基对、一氧化碳、氢气和一个醛，其中碱基对包括一个氨基甲酰化合物和一个羧甲基化催化剂前体。在一个首选实施例中，选择氨基甲酰化合物和醛以产生一种容易转化为N-(磷酸甲基)甘氨酸或其盐或酯的N-酰基氨基羧酸。
• Preparation of N-acyl amino carboxylic acids, amino carboxylic acids and their derivatives by metal-catalyzed carboxymethylation in the presence of a promoter
  申请人：——

  公开号：US20020058834A1

  公开（公告）日：2002-05-16

  A process for the preparation of amino carboxylic acids, N-acyl amino carboxylic acids, or derivatives thereof by carboxymethylation of an amide, amide precursor or amide source compound in the presence of a carboxymethylation catalyst precursor and a promoter is provided. A carboxymethylation reaction mixture is formed by introducing a promoter, an amide, amide precursor or amide source compound, carbon monoxide, hydrogen, an aldehyde or aldehyde source compound, and a carboxymethylation catalyst precursor into a carboxymethylation reaction zone. In a preferred embodiment, the promoter is a supported noble metal promoter. In another preferred embodiment, the amide compound and aldehyde are selected to yield an N-acyl amino carboxylic acid which is readily converted to N-phosphonomethyl)glycine, or a salt or ester thereof.

  本发明提供了一种通过在存在羧甲基化催化剂前体和促进剂的情况下对酰胺、酰胺前体或酰胺源化合物进行羧甲基化制备氨基羧酸、N-酰基氨基羧酸或其衍生物的方法。通过将促进剂、酰胺、酰胺前体或酰胺源化合物、一氧化碳、氢、醛或醛源化合物和羧甲基化催化剂前体引入羧甲基化反应区域形成羧甲基化反应混合物。在一种优选实施方式中，促进剂是支持的贵金属促进剂。在另一种优选实施方式中，所选择的酰胺化合物和醛可产生易于转化为(N-磷酸甲基)甘氨酸或其盐或酯的N-酰基氨基羧酸。
• Method for the synthesis of N-(phosphonomethyl)glycine
  申请人：STRAITMARK HOLDING AG

  公开号：US09150599B2

  公开（公告）日：2015-10-06

  A method for the synthesis of N-(phosphonomethyl) glycine or one of its derivatives selected from the group of its salts, its phosphonate esters and its phosphonate ester salts, including the steps of: a) forming a reaction mixture having an acid catalyst, N,N′-bis(carboxymethyl)-2,5-diketopiperazine and a compound having one or more P—O—P anhydride moieties, wherein the moieties have one P atom at the oxidation state (+III) and the other P atom at the oxidation state (+III) or (+V), to form N,N′-bis(phosphonomethyl)-2,5-diketopiperazine, its dehydrated forms or their phosphonate esters; b) hydrolyzing the reaction mixture to form N-(phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.

  一种合成N-(磷酸甲基)甘氨酸或其盐类、磷酸酯或磷酸酯盐类衍生物的方法，包括以下步骤：a）形成反应混合物，其中包括酸催化剂、N,N′-双(羧甲基)-2,5-二酮哌嗪和具有一个或多个P—O—P酐基团的化合物，其中酐基团具有一个P原子在氧化态(+III)，另一个P原子在氧化态(+III)或(+V)，以形成N,N′-双(磷酸甲基)-2,5-二酮哌嗪、其脱水形式或其磷酸酯；b）水解反应混合物，以形成N-(磷酸甲基)甘氨酸或其盐类、磷酸酯或磷酸酯盐类衍生物之一。
• The effect of earth metal ion on the property of peptide-based metal–organic frameworks
  作者：Wu-lin Chen、Wen-Xian Chen、Gui-lin Zhuang、Jun Zheng、Li Tan、Xing Zhong、Jian-guo Wang

  DOI：10.1039/c3ce40587g

  日期：——

  A series of alkaline earth metal-based bio-analogous metal–organic frameworks (1–4) based on a cyclic dipeptide (2,5-piperazinedione-1,4-diacetic acid, H2PODC) were prepared under the same synthetic conditions and the effect of earth metal ion on the (geometrical and electronic) property of these MOFs was investigated. Crystal analysis demonstrates that the metal ion radii play an important role in coordination number, coordination modes of the ligand and bond length. The binding mode between metal ion and peptide can be divided into two groups: (1) Mg2+ and Sr2+; (2) Ca2+ and Ba2+ ions, where the difference is whether the carbonyl group participates in coordination. The result may be relevant to the different biophysical phenomena of protein between alkaline earth metal ions. UV-vis spectra show two adsorption peaks for compounds 1–4, while fluorescence spectra display one emission peak. Via first-principles density functional theory (DFT) calculation, we found that two adsorption peaks should be attributed to the transition of valence band (VB) → two empty bands and VB → conduction band (CB), while one emission peak may result from the transition of CB → VB.

  在相同的合成条件下，基于环状二肽（2,5-哌嗪二酮-1,4-二乙酸，H2PODC）制备了一系列碱土金属基生物类金属有机骨架（1-4），并研究了碱土金属离子对这些MOF（几何和电子）性质的影响。晶体分析表明，金属离子的半径在配位数、配体的配位方式和键长中起着重要作用。金属离子和肽之间的结合方式可分为两类：（1）Mg2+和Sr2+；（2）Ca2+和Ba2+离子，区别在于羰基是否参与配位。结果可能与碱土金属离子之间蛋白质的不同生物物理现象有关。紫外可见光谱显示化合物1-4有两个吸附峰，而荧光光谱显示一个发射峰。通过第一性原理密度泛函理论（DFT）计算，我们发现两个吸附峰应归因于价带（VB）→两个空带和VB→导带（CB）的跃迁，而一个发射峰可能是由CB→VB的跃迁引起的。