tetramethyl 5,5'-[terephthaloylbis(azanediyl)]diisophthalate | 349098-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tetramethyl 5,5'-[terephthaloylbis(azanediyl)]diisophthalate
• 英文别名: methyl 3-[(4-{[(3-(methoxycarbonyl)-5(methoxycarbonyl)phenyl)amino]carbonyl}benzoyl)amino]-5-(methoxycarbonyl)benzoate；Tetramethyl 5,5'-(terephthaloylbis(azanediyl))-diisophthalate；dimethyl 5-[[4-[[3,5-bis(methoxycarbonyl)phenyl]carbamoyl]benzoyl]amino]benzene-1,3-dicarboxylate
• CAS: 349098-14-2
• 化学式: C₂₈H₂₄N₂O₁₀
• 分子量: 548.506
• InChiKey: RLZQINXRCVKHGV-UHFFFAOYSA-N

物化性质

• 熔点：
  303-306 °C
• 沸点：
  603.3±55.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tetramethyl 5,5'-[terephthaloylbis(azanediyl)]diisophthalate 在 sodium hydroxide 作用下， 反应 2.0h， 以77%的产率得到5,5'-(对苯二甲酰基双(氮杂二基))二间苯二甲酸
  参考文献：
  名称：

  Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity

  摘要：

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.

  DOI：

  10.1021/jm049922t
• 作为产物：
  描述：

  5-氨基间苯二甲酸 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 tetramethyl 5,5'-[terephthaloylbis(azanediyl)]diisophthalate
  参考文献：
  名称：

  含有36和24倍酰胺基团的金属有机多面体，用于选择性发光识别天然二糖。

  摘要：

  获得了八核双冠co Ce基三棱柱和四核分子四面体，它们在主骨架中包含36和24倍的酰胺，并在结构上表征了乳糖和蔗糖相对于其他相关的天然单糖和蔗糖的选择性发光识别。二糖。

  DOI：

  10.1039/c2cc30497j

文献信息

• Synthesis, Characterization, Crystal Structure and Fluorescence Property of Tetramethyl 5,5′-(Terephthaloylbis(azanediyl))-Diisophthalate
  作者：Qingfu Zhang、Aijing Geng、Zhipeng Liu、Yang Shi、Dezhi Sun

  DOI：10.1007/s10870-012-0367-9

  日期：2012.11

  An aroyl acylamide compound, tetramethyl 5,5′-(terephthaloylbis(azanediyl))-diisophthalate (1), has been prepared by nucleophilic substitution reaction of dimethyl 5-aminoisophthalate and terephthaloyl chloride, and characterized by elemental analysis, FT-IR, 1H-NMR, ESI–MS and single-crystal X-ray diffraction. The crystal of 1·2DMF belongs to monoclinic space group P2/c with a = 21.609(2) Å, b = 4.060(1) Å, c = 21.606(2) Å, β = 112.805(1)°, V = 1747.4(3) Å3, Z = 2, D c  = 1.320 Mg m−3, μ = 0.101 mm−1, F(000) = 732, M r  = 694.68, the final R 1 = 0.0879 and wR 2 = 0.1872 for 8091 observed reflections with I > 2σ(I). The structural analysis reveals that compound 1·2DMF contains one tetramethyl 5,5′-(terephthaloylbis-(azanediyl))-diisophthalate and two N,N-dimethylformamide solvent molecules. A 3D supramolecular structure of 1·2DMF is constructed by multiply intermolecular C–H···O H-bonds and π–π stacking interactions. In addition, compound 1 exhibits a strong blue fluorescence at 413 nm in the solid state at room temperature. An aroyl acylamide compound, tetramethyl 5,5′-(terephthaloylbis(azanediyl))-diisophthalate (1), has been prepared and characterized by elemental analysis, FT-IR, 1H-NMR, ESI–MS, single-crystal X-ray diffraction and fluorescence spectra.

  通过 5-氨基间苯二甲酸二甲酯和对苯二甲酰氯的亲核取代反应，制备了一种芳基酰酰胺化合物--5,5′-(对苯二甲酰双(偶氮二基))-二间苯二甲酸四甲酯(1)，并通过元素分析、傅立叶变换红外光谱、1H-核磁共振、ESI-MS 和单晶 X 射线衍射进行了表征。1-2DMF 晶体属于单斜空间群 P2/c，a = 21.609(2)埃，b = 4.060(1) 埃，c = 21.606(2) Å, β = 112.805(1)°, V = 1747.4(3) Å3, Z = 2, D c  = 1.320 Mg m-3, μ = 0.101 mm-1, F(000) = 732, M r  = 694.68、最终 R 1 = 0.0879，wR 2 = 0.1872，观察到 8091 个与 I > 2σ(I) 的反射。结构分析表明，化合物 1-2DMF 含有一个 5,5′-(对苯二甲酰双偶氮二基)-二间苯二甲酸四甲基酯和两个 N,N-二甲基甲酰胺溶剂分子。1-2DMF 的三维超分子结构是由分子间多重 C-H-O H 键和π-π堆叠相互作用构建而成的。此外，化合物 1 在室温固态下于 413 nm 处显示出强烈的蓝色荧光。通过元素分析、傅立叶变换红外光谱、1H-NMR、ESI-MS、单晶 X 射线衍射和荧光光谱，制备了一种芳基酰酰胺化合物--5,5′-（对苯二甲酰基双（偶氮二基））-二间苯二甲酸四甲酯（1），并对其进行了表征。
• Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity
  作者：Shane Sellarajah、Tamuna Lekishvili、Claire Bowring、Andrew R. Thompsett、Helene Rudyk、Christopher R. Birkett、David R. Brown、Ian H. Gilbert

  DOI：10.1021/jm049922t

  日期：2004.10.1

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.
• Metal–organic polyhedra containing 36 and 24 folds of amide groups for selective luminescent recognition of natural disaccharides
  作者：Yang Jiao、Jing Zhang、Lejie Zhang、Zhihua Lin、Cheng He、Chunying Duan

  DOI：10.1039/c2cc30497j

  日期：——

  An octa-nuclear bicoronal Ce-based triangular prism and tetra-nuclear molecular tetrahedron containing 36 and 24 folds amides within their main backbones were achieved and structurally characterized for the selective luminescent recognition of lactose and sucrose, respectively, over other related natural mono- and disaccharides.

  获得了八核双冠co Ce基三棱柱和四核分子四面体，它们在主骨架中包含36和24倍的酰胺，并在结构上表征了乳糖和蔗糖相对于其他相关的天然单糖和蔗糖的选择性发光识别。二糖。