NCI 344032 | 72583-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: NCI 344032
• 英文别名: N,N,N',N'-tetrakis(1H-benzimidazol-2-ylmethyl)ethane-1,2-diamine
• CAS: 72583-85-8
• 化学式: C₃₄H₃₂N₁₀
• 分子量: 580.695
• InChiKey: WFVZBDCRUPTVOM-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  988.4±65.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  NCI 344032 在 高氯酸 、 水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以71%的产率得到
  参考文献：
  名称：

  Anion directed supramolecular architecture of benzimidazole-based receptor

  摘要：

  The reaction of N,N,N,N'-tetralds-(1H,benzimidazol-2ylmethyl)ethane-1,2-diamine (L) with different inorganic as well as organic acid afford salts viz., LH44+center dot 4ClO(4)(-)center dot 4H(2)O (1), LH44+center dot 4Br(-)center dot 4(CH3)(2)SO (2), 2LH(3)(3+)center dot 3SiF(6)(2-)center dot 14H(2)O (3), LH44+center dot 4H(2)PO(4)(-)center dot 2H(3)PO(4) (4) and L center dot 2CH(3)COOH (5) with different structures. The X-ray crystallographic studies revealed that these compounds are all ionic in nature due to proton transfer except 5 and are stabilized in the solid state by networks of hydrogen bonds between their respective components as well as solvent molecules. It also demonstrates that different types of hydrogen bond between protonated ligand and the anions are responsible for the extensive supramolecular frame work. The three dimensional packing is mainly guided by well-balanced primary N-H center dot center dot center dot O, O-H center dot center dot center dot N, O-H center dot center dot center dot O hydrogen bonds and secondary C-H center dot center dot center dot O interactions between benzimidazole and acids. Moreover, the hydrogen bonds, pi center dot center dot center dot pi it and C-H center dot center dot center dot pi stacking interactions appear to be effective in stabilizing the crystal structures. The colorimetric test showed color change upon the addition of acids in solution of the ligand. The photo-physical experiments suggest that the ligand shows fluorescence properties in the presence of acids. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.10.008
• 作为产物：
  描述：

  乙二胺四乙酸 、 邻苯二胺 以 乙二醇 为溶剂， 反应 8.0h， 以85%的产率得到NCI 344032
  参考文献：
  名称：

  具有两个醇盐-Fe(III) 中心的脂加氧酶模型：合成、结构和性质

  摘要：

  摘要 [Fe III (OMe)(Hedtb)](ClO 4 ) 3 ·6.5CH 3 OH ( 1 ) 和 [Fe III (O n- Bu)(Hedtb)](ClO 4 ) 3 ·3 n- BuOH ( 2 ) (edtb = N,N,N',N'-四[(2-苯并咪唑基)甲基]-1,2-乙二胺)并显示出脂氧合酶活性。X 射线晶体学显示配合物1和2中的 Fe III中心与 edtb 配体的三个苯并咪唑氮和两个烷基胺氮原子连接，末端烷氧基占据第六位。配合物1和2都具有 Fe III -O R中心 ( R  = Me, 1 ; n -Bu, 2 )，Fe-O 键距离分别为 1.799(3) Å 和 1.789(5) Å。记录了配合物的紫外-可见光谱和电化学性质。两种复合物在 375 nm 附近都有强吸收峰，并显示出脂氧合酶活性。

  DOI：

  10.1134/s0022476622040151

文献信息

• 一种多苯并咪唑类配合物及其制备方法和用 途
  申请人：华中师范大学

  公开号：CN106008561B

  公开（公告）日：2018-11-30

  本发明公开了一种多苯并咪唑类配合物，及其制备方法和用途。以多元胺羧酸或二羧酸与邻苯二胺为起始原料，合成所需配体多苯并咪唑类化合物；将配体多苯并咪唑类化合物与CuCl2，Cu(NO3)2或Cu(ClO4)2反应，合成多苯并咪唑类配合物。所述多苯并咪唑类配合物可以作为铜锌超氧化物氧化酶(SOD1)的模拟物，具有提高植物抗干旱胁迫能力的作用。
• Synthesis, Crystal Structure and Hirshfeld Surface Analysis of [Cu(EDTB)][CdBr4]·H2O (EDTB = N,N,N′,N′-tetrakis-[(2-benzimidazolyl)methyl]-1,2-ethanediamine)
  作者：Sisi Feng、Shidong Qin、Guoqin Feng、Xiuxiu Han、Miaoli Zhu

  DOI：10.1007/s10870-012-0292-y

  日期：2012.6

  N,N,N′,N′-tetrakis-[(2-benzimidazolyl)methyl]-1,2-ethanediamine (EDTB), a multidentate ligand, was synthesized by refluxing of EDTA and o-phenylenediamine in glycol with a molar ratio of 1:4. Reaction of the 2:1:1 stoichiometric proportion of EDTB with cadmium(II) bromide and copper(II) bromide in methanol and distilled water affords a mononuclear copper(II) complex, [Cu(EDTB)][CdBr4]·H2O (1), which

  N,N,N',N'-四-[(2-苯并咪唑基)甲基]-1,2-乙二胺(EDTB)，一种多齿配体，通过EDTA和邻苯二胺在乙二醇中以摩尔比回流合成1:4。化学计量比为 2:1:1 的 EDTB 与溴化镉 (II) 和溴化铜 (II) 在甲醇和蒸馏水中反应得到单核铜 (II) 络合物 [Cu(EDTB)][CdBr4]·H2O ( 1)，在单斜空间群 P21/c 中结晶，a = 12.226(3), b = 20.948(5), c = 19.330(3) Å, β = 116.597(11)°, V = 4426.7(17) Å3 和 Z = 4。[Cu(EDTB)]2+ 阳离子通过 N–H…Br 和 N–H…O 氢键连接到 [CdBr4]2- 阴离子和水分子。此外，C–H…Br、C–H…π 和 π…π 弱相互作用也将这些单元连接成二维结构。使用 Hirshfeld 表面分析对晶体堆积和分子间
• Benzimidazole and Related Ligands for Cu-Catalyzed Azide−Alkyne Cycloaddition
  作者：Valentin O. Rodionov、Stanislav I. Presolski、Sean Gardinier、Yeon-Hee Lim、M. G. Finn

  DOI：10.1021/ja072678l

  日期：2007.10.1

  Tris(2-benzimidazolylmethyl)amines have been found to be superior accelerating ligands for the copper(I)-catalyzed azide-alkyne cycloaddition reaction. Candidates bearing different benzimidazole N-substituents as well as benzothiazole and pyridyl ligand arms were evaluated by absolute rate measurements under relatively dilute conditions by aliquot quenching kinetics and by relative rate measurements

  已发现三（2-苯并咪唑基甲基）胺是铜（I）催化的叠氮化物-炔环加成反应的优异加速配体。带有不同苯并咪唑 N 取代基以及苯并噻唑和吡啶基配体臂的候选物通过在相对稀释条件下通过等分淬火动力学进行的绝对速率测量和在浓缩条件下通过反应量热法进行的相对速率测量进行评估。具有侧链烷基羧酸盐臂的苯并咪唑基配体被证明在后一种情况下是有利的。该催化剂系统显示出包含不止一种活性物质，对 pH 值和缓冲盐的变化提供复杂的响应，并在高浓度配位配体的存在下保持高催化速率。
• Functional heterometallic coordination polymers with metalloligands as tunable luminescent crystalline materials
  作者：Dong-Ying Du、Jun-Sheng Qin、Cheng-Xin Sun、Xin-Long Wang、Shu-Ran Zhang、Ping Shen、Shun-Li Li、Zhong-Min Su、Ya-Qian Lan

  DOI：10.1039/c2jm34661c

  日期：——

  Five heterometallic luminescent crystalline materials with the metalloligand, [Zn(HL)EuxTby(H2O)2][ZnBr4]·H2O (x = 1, y = 0, IFMC-21; x = 0.75, y = 0.25, IFMC-22; x = 0.5, y = 0.5, IFMC-23; x = 0.25, y = 0.75, IFMC-24; x = 0, y = 1, IFMC-25; H4L = 4,4′,4′′,4′′′-(2,2′,2′′,2′′′-(ethane-1,2-diylbis(azanetriyl))tetrakis(methylene)-tetrakis-(1H-benzo[d]imidazole-2,1-diyl))tetrakis(methylene)-tetrabenzoic acid; IFMC = Institute of Functional Material Chemistry), were prepared by the combination of hydrothermal and ionothermal methods for the first time. IFMC-21–25 can be obtained by introducing the desired Eu(III) and Tb(III) in the initial experiments. In these crystalline materials, the metalloligand Zn(HL) was connected by bi-lanthanide cores leading to a 2D sheet-structure and [ZnBr4]2− ions were distributed in the interspaces of the sheet. The luminescent properties of IFMC-21 to 25 were investigated and the results reveal that they exhibit characteristic Eu(III) and Tb(III) ion emissions, and the intensities of red and green arising from Eu(III) and Tb(III) emissions are shifted correspondingly by tuning the ratios of Eu(III) : Tb(III).

  含有金属配体[Zn(HL)EuxTby(H2O)2][ZnBr4]- 的五种异金属发光晶体材料（x = 1，y = 0，IFMC-21；x = 0.75，y = 0.25，IFMC-22；x = 0.5，y = 0.5，IFMC-23；x = 0.25，y = 0.75，IFMC-24；x = 0，y = 1，IFMC-25；H4L = 4,4′,4′′,4′′′-(2,2′,2′′,2′′′-(乙烷-1,2-二基双(氮杂环丁三基))四(亚甲基)-四(1H-苯并[d]咪唑-2,1-二基))四(亚甲基)-四苯甲酸；IFMC = 功能材料化学研究所），首次采用水热法和离子热法相结合的方法制备。在初始实验中引入所需的 Eu（III）和 Tb（III）即可得到 IFMC-21-25。在这些晶体材料中，金属配体 Zn(HL) 由双镧系元素核连接，形成二维片状结构，[ZnBr4]2- 离子分布在片状结构的间隙中。对 IFMC-21 至 25 的发光特性进行了研究，结果表明它们表现出特征性的 Eu（III）和 Tb（III）离子发射，并且通过调整 Eu（III）和 Tb（III）的比例，Eu（III）和 Tb（III）发射的红色和绿色的强度会发生相应的变化：锑（III）的比率，红色和绿色的强度也会相应地发生变化。
• Self-Assembly versus Stepwise Synthesis: Heterometal-Organic Frameworks Based on Metalloligands with Tunable Luminescence Properties
  作者：Shu-Ran Zhang、Dong-Ying Du、Ke Tan、Jun-Sheng Qin、Hui-Qing Dong、Shun-Li Li、Wen-Wen He、Ya-Qian Lan、Ping Shen、Zhong-Min Su

  DOI：10.1002/chem.201301536

  日期：2013.8.19

  A new family of heterometal–organic frameworks has been prepared by two synthesis strategies, in which IFMC‐26 and IFMC‐27 are constructed by self‐assembly and IFMC‐28 is obtained by stepwise synthesis based on the metalloligand (IFMC=Institute of Functional Material Chemistry). IFMC‐26 is a (3,6)‐connected net and IFMC‐27 is a (4,8)‐connected 3D framework. The metalloligands Ni(H4L)}(NO3)2 are connected

  通过两种合成策略制备了一个新的杂金属-有机骨架家族，其中IFMC-26和IFMC-27是通过自组装构建的，而IFMC-28是通过基于金属配体的逐步合成而获得的（IFMC =功能性研究所材料化学）。IFMC‐26是（3,6）连接的网络，而IFMC‐27是（4,8）连接的3D框架。金属配体Ni（H 4 L）}（NO 3）2通过双核镧系元素簇连接，从而在IFMC‐28中形成2D薄板结构。值得注意的是，IFMC‐26‐Eu x Tb y和IFMC‐28‐Eux Tb y是通过改变原料的摩尔比获得的。由于孔隙率IFMC-26，铽3+ @ IFMC-26铕和铕3+ @ IFMC-26-Tb的由铽postencapsulating得到III及EuIII，离子分别进气孔。金属有机骨架中的可调发光是通过两种掺杂方法实现的。特别是，LnIII离子的后封装明显提高了杂金属-有机骨架的量子产率。