N,N',N''-(Nitrilotriethylene)trisphthalimide | 27160-19-6

• 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',N''-(Nitrilotriethylene)trisphthalimide
• 英文别名: tris(2-phthalimidoethyl)amine；tris-(2-phthalimido-ethyl)-amine；Tris-(2-phthalimido-aethyl)-amin；2,2',2''-Triphthalimidotriethylamin；2-[2-[Bis[2-(1,3-dioxoisoindol-2-yl)ethyl]amino]ethyl]isoindole-1,3-dione
• CAS: 27160-19-6
• 化学式: C₃₀H₂₄N₄O₆
• 分子量: 536.544
• InChiKey: NWQKMFGMPGVYCL-UHFFFAOYSA-N

物化性质

• 沸点：
  720.4±55.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 N,N',N''-(Nitrilotriethylene)trisphthalimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 Tris-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-methyl-ammonium; sulfate
  参考文献：
  名称：

  Synthesis and Structure of the Methylated Tren Derivative N,N,N-Tris(2-aminoethyl)-N-methylammonium Chloride Trihydrochloride

  摘要：

  详细介绍了新的趋势衍生物 N,N,N-三(2-氨基乙基)-N-甲基氯化铵三盐酸盐的合成和 X 射线晶体结构。该化合物是通过使用硫酸二甲酯将三(2-邻苯二甲酰亚胺基乙基)胺甲基化，然后进行酸脱保护而合成的。N,N,N-三(2-氨乙基)-N-甲基氯化铵三盐酸盐在六方空间群 P63 中结晶，X 射线晶体结构显示了阳离子与两种不同类型的氯离子广泛氢键结合的一维链，其中一种阳离子的配位数为 9。该阳离子对 CoIII 和 NiII 的配位性都很差。

  DOI：

  10.1071/ch02060
• 作为产物：
  描述：

  N-(2-溴乙基)邻苯二甲酰亚胺 在 氨 作用下， 生成 N,N',N''-(Nitrilotriethylene)trisphthalimide
  参考文献：
  名称：

  Ristenpart, Chemische Berichte, 1896, vol. 29, p. 2530

  摘要：

  DOI：

文献信息

• General method for the synthesis of trishydroxamic acids
  作者：V. Karunaratne、H.R. Hoveyda、C. Orvig

  DOI：10.1016/s0040-4039(00)74153-0

  日期：1992.3

  Triscarboxylic acids, when treated with hydroxylamines in the presence of water-soluble carbodiimide in THF-H2O, at pH≈4.8, yield the corresponding trishydroxamic acids in good yields.

  在水溶性碳二亚胺在THF-H 2 O中，pH≈4.8的条件下，用羟胺处理三羧酸时，可以得到相应的三异羟肟酸，收率很高。
• 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...
• Gupta, Shilpi; Jalal, Sarah; Kumar, Sumit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 9, p. 1376 - 1387
  作者：Gupta, Shilpi、Jalal, Sarah、Kumar, Sumit、Haag, Rainer、Sharma, Sunil K.

  DOI：——

  日期：——
• Mann; Pope, Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences, 1925, vol. 109, p. 447
  作者：Mann、Pope

  DOI：——

  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.