N,N'-bis(2-phthalimidoethyl)piperazine | 20541-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N,N'-bis(2-phthalimidoethyl)piperazine
• 英文别名: 1,4-bis(2-phthalimidoethyl)piperazine；N,N'-(2,2'-piperazine-1,4-diyl-diethyl)-bis-phthalimide；1,4-bis-(2-phthalimido-ethyl)-piperazine；1,4-Bis-(2-phthalimido-aethyl)-piperazin；N,N'-di-(2-phthalimidoethyl)-piperazine；2,2'-(piperazine-1,4-diyldiethane-2,1-diyl)bis(1H-isoindole-1,3(2H)-dione)；2-[2-[4-[2-(1,3-dioxoisoindol-2-yl)ethyl]piperazin-1-yl]ethyl]isoindole-1,3-dione
• CAS: 20541-87-1
• 化学式: C₂₄H₂₄N₄O₄
• mdl: MFCD00624391
• 分子量: 432.479
• InChiKey: REXXZWXXIILZEH-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C
• 沸点：
  618.4±50.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-phthalimidoethyl)piperazine 在 肼 作用下， 生成 1,4-哌嗪二乙胺
  参考文献：
  名称：

  含氮杂环衍生物的结构对其抗流感活性的影响

  摘要：

  建立了基于分子结构单纯形表示的适当QSAR模型，以优化对新抗流感药物的搜索。该模型的结构解释使我们能够鉴定出分子片段，这些分子片段决定了化合物对抗人类流感病毒的活性。进一步的虚拟筛选和靶向合成使我们能够选择一组潜在有效的化合物，其中最优选的是哌啶和异吲哚啉的衍生物中的三种。

  DOI：

  10.1007/s10593-019-02479-5
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 potassium carbonate 作用下， 反应 0.17h， 生成 N,N'-bis(2-phthalimidoethyl)piperazine
  参考文献：
  名称：

  Ganin, E.V.; Makarov, V.F.; Nikitin, V.I., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 330 - 332

  摘要：

  DOI：

文献信息

• The Reaction of Phthalic Anhydride with Diethylenetriamine and Triethylenetetramine. A Literature Correction
  作者：Anatoli Onopchenko、James J. Harrison、Carrie Y. Chan

  DOI：10.1246/bcsj.71.717

  日期：1998.3

  reported in the literature are attributed to branched and cyclic amines in their triethylenetetramine, and not to rearrangement reactions. Such possibility is supported by analysis of triethylenetetramine from the same supplier (ca. 65% linear), and our failure to duplicate the results with an authentic triethylenetetramine. Several reported compounds were prepared from pure ami...

  重新研究了邻苯二甲酸酐与二亚乙基三胺在乙酸中反应生成双(2-邻苯二甲酰亚胺乙基)胺邻苯二甲酸氢盐的报道。我们获得的主要产品是双（2-邻苯二甲酰亚胺乙基）胺、一些酰胺和很少的盐。使用线性三亚乙基四胺，我们没有得到 N,N'-双（2-邻苯二甲酰亚胺乙基）乙二胺，也没有报道重排的三（2-邻苯二甲酰亚胺乙基）胺或 1,4-双（2-邻苯二甲酰亚胺乙基）哌嗪。一种新型酰胺——2-N-2-邻苯二甲酰亚胺乙基-N-[2-(2-邻苯二甲酰亚胺乙基)氨基乙基]氨基甲酰基}苯甲酸——作为主要产物而形成。文献中报道的产物归因于其三亚乙基四胺中的支链和环状胺，而不是重排反应。这种可能性得到了来自同一供应商的三亚乙基四胺的分析（约 65% 线性）的支持，并且我们未能用真正的三亚乙基四胺复制结果。几个报道的化合物是由纯胺制备的...
• Use of 1,4-bis (3-aminoalkyl) piperazine derivatives in the treatment of neurodegenerative diseases
  申请人：Sergeant Nicolas

  公开号：US20090149464A1

  公开（公告）日：2009-06-11

  Use of 1,4-bis(3-aminoalkyl)piperazine derivatives as defined in formula I or II for the manufacture of a pharmaceutical composition intended for the treatment of neurodegenerative diseases, related neurodegenerative diseases, developmental diseases or cancer. The instant invention is also directed to some specific 1,4-bis(3-aminoalkyl)piperazine derivatives and pharmaceutical composition including them.

  使用公式I或II中定义的1,4-双(3-氨基烷基)哌嗪衍生物制造用于治疗神经退行性疾病、相关神经退行性疾病、发育性疾病或癌症的药物组合物。本发明还涉及一些特定的1,4-双(3-氨基烷基)哌嗪衍生物和包括它们的药物组合物。
• v. Braun; Goll; Metz, Chemische Berichte, 1926, vol. 59, p. 2423
  作者：v. Braun、Goll、Metz

  DOI：——

  日期：——
• CCCCXXVII.—Attempts to find new antimalarials. Part VII. Quinoline compounds having in the 4-position a side chain containing two or more nitrogen atoms
  作者：William Ogilvy Kermack、James Fergus Smith

  DOI：10.1039/jr9310003096

  日期：——
• Preparations, Crystal Structures, and Unusual Proton NMR Characteristics of Some Phthalimides
  作者：Dawn M. Y. Barrett、Ishenkumba A. Kahwa、Joel T. Mague、Gary L. McPherson

  DOI：10.1021/jo00123a035

  日期：1995.9

  Protection of NH2 groups as phthalimides using a mixture of acetic acid, phthalic anhydride, and the relevant polyamine can take unusual routes. For diethylenetriamine the major product is diphthalimidodiethylammonium-hydrogen phthalate (DPDAH-HP). For triethylenetetraamine, ethylene migration products N,N-bis(2-phthalimidoethyl)piperazine (2) and N,N',N''-(nitrilotriethylene)trisphthalimide (3) were obtained from room temperature and refluxing reaction mixtures, respectively. The crystal structures of 2, 3, and DPDAH-HP were determined and reveal a series of stabilizing complementary interactions for these favored products (i.e., offset pi-pi stacking and C-H...O and possibly C-H N hydrogen bonds (2), electrostatic interactions between the amine and pyrrolic functionalities (3), and offset pi-pi stacking and N-H...O hydrogen bonding (DPDAH-HP)). The DPDAH-HP units stack along a screw axis parallel to the b-direction to yield a striking [phthalimide-phthalimide-hydrogen phthalate](n) motif and are linked in the a and c directions by N-H...O bonds. Solution H-1 NMR studies of 3 reveal unusual temperature (178-420 K) evolution of sharp aromatic proton resonances in various solvents. Typically, the spectra exhibit a spectacular temperature evolution from a sharp doublet of quartets at high temperature to complex second-order behavior and then a singlet. As the temperature is further lowered, a complex second order spectrum reappears followed by a doublet of quartets. The phthalimide-amine interaction energy, determined from temperature dependent NMR studies, is ca. 20 kJ/mol. Solid state C-13 aromatic resonances are broadened by pi-pi interactions in 2 and DPDAH-HP while two sets of C-13 resonances are found for 3 as expected from the solid state structures. The hydrogen phthalate anion in DPDAH-HP exchanges rapidly with free phthalic acid (equilibrium constant, K similar or equal to 4 x 10(2) L/mol); this phthalate exchange exhibits almost temperature independent behavior indicating that it is predominantly entropy driven.