4'-(diethylenetriamino-N,N',N'',N''-tetraacetate)-2,2':6,2''-terpyridine | 708986-68-9

• 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: 4'-(diethylenetriamino-N,N',N'',N''-tetraacetate)-2,2':6,2''-terpyridine
• 英文别名: H4(tpy-DTTA)；(2,2':6',2''-terpyridine)(diethylenetriamine-N,N,N'',N''-tetraacetic acid)；2-[2-[2-[Bis(carboxymethyl)amino]ethyl-(2,6-dipyridin-2-ylpyridin-4-yl)amino]ethyl-(carboxymethyl)amino]acetic acid；2-[2-[2-[bis(carboxymethyl)amino]ethyl-(2,6-dipyridin-2-ylpyridin-4-yl)amino]ethyl-(carboxymethyl)amino]acetic acid
• CAS: 708986-68-9
• 化学式: C₂₇H₃₀N₆O₈
• 分子量: 566.571
• InChiKey: VHHIOPVBTRDBLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  198
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  铁粉 、 4'-(diethylenetriamino-N,N',N'',N''-tetraacetate)-2,2':6,2''-terpyridine 以 水 为溶剂， 生成 [Fe(2,2':6',2''-terpyridine)(diethylenetriamine-N,N,N'',N''-tetraacetate)2](6-)
  参考文献：
  名称：

  Novel heteroditopic chelate for self-assembled gadolinium(iii) complex with high relaxivityElectronic Supplementary Information (ESI) available: synthesis and analytical data for tpy-DTTA4? and for the complexes. See http://www.rsc.org/suppdata/cc/b4/b400169a/

  摘要：

  [Fe(tpy-DTTA)2Gd2]是一种基于新型配体的自组装三核复合物，其中联苯吡啶和聚（氨基羧酸）部分相连；它具有明确的拓扑结构，有利于实现高磁化率，即刚性FeII(tpy)2核心，由于短连接子而降低了外围的灵活性，以及两个GdIII中心的有效分离。

  DOI：

  10.1039/b400169a
• 作为产物：
  描述：

  4'-氯-2,2':6',2''-三联吡啶 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 4'-(diethylenetriamino-N,N',N'',N''-tetraacetate)-2,2':6,2''-terpyridine
  参考文献：
  名称：

  Novel heteroditopic chelate for self-assembled gadolinium(iii) complex with high relaxivityElectronic Supplementary Information (ESI) available: synthesis and analytical data for tpy-DTTA4? and for the complexes. See http://www.rsc.org/suppdata/cc/b4/b400169a/

  摘要：

  [Fe(tpy-DTTA)2Gd2]是一种基于新型配体的自组装三核复合物，其中联苯吡啶和聚（氨基羧酸）部分相连；它具有明确的拓扑结构，有利于实现高磁化率，即刚性FeII(tpy)2核心，由于短连接子而降低了外围的灵活性，以及两个GdIII中心的有效分离。

  DOI：

  10.1039/b400169a

文献信息

• Rigid M^IIL₂Gd₂^III (M = Fe, Ru) Complexes of a Terpyridine-Based Heteroditopic Chelate:  A Class of Candidates for MRI Contrast Agents
  作者：Jérôme Costa、Robert Ruloff、László Burai、Lothar Helm、André E. Merbach

  DOI：10.1021/ja0424169

  日期：2005.4.1

  Rigid chelates of high-molecular weight, [M(tpy-DTTA)(2)](6-) (M = Fe, Ru), are obtained upon self-assembly around one M-II ion of two terpyridine-based molecules substituted in the 4'-position with the polyaminocarboxylate diethylenetriamine-N,N,N",N"-tetraacetate, tpy-DTTA(4-). The protonation constants of tpy-DTTA(4-) (log K-1 = 8.65(4), log K-2 = 7.63(4), log K-3 = 5.25(6), log K-4 = 3.30(7)) and [Fe(tpy-DTTA)(2)](6-) (log K-1 = 8.40(4), log K-2 = 7.26(4)) have been determined by potentiometry, H-1 NMR and UV-vis titrations. The thermodynamic stability constant log K-GdL of [Fe(tpy-DTTA)(2)Gd-2(H2O)(4)] measured at 25 degrees C by potentiometry is 10.87. This relatively low value is due to the direct linkage of the polyaminocarboxylate part to the electron-withdrawing terpyridine. UV-vis absorbance spectra of [M(tpy-DTTA)2Gd2(H2O)4] and H-1 NMR spectra of [M(tpy-DTTA)(2)Eu-2(H2O)(4)] revealed similar solution behavior of the Fe and Ru complexes. An Id water-exchange mechanism (Delta V-double dagger = +6.8 +/- 1 cm(3) mol(-1)) with a rate constant of k(ex)(298) = (5.1 +/- 0.3) x 10(6) s(-1) has been found for [Fe(tpy-DTTA)(2)Gd-2(H2O)(4)] by O-17 NMR. A slow rotational correlation time (tau(RO) = 410 +/- 10 ps) and the presence of two water molecules (q = 2) in the coordination inner-sphere of each Gd-III ion have also been determined for this complex. A remarkably high relaxivity has been observed for both [M(tpy-DTTA)(2)Gd-2(H2O)(4)] complexes (at 20 MHz and 37 degrees C, r(1) = 15.7 mM(-1) s(-1) for the Fe complex, and r(1) = 15.6 mM(-1) s(-1) for the Ru complex).
• Novel heteroditopic chelate for self-assembled gadolinium(iii) complex with high relaxivityElectronic Supplementary Information (ESI) available: synthesis and analytical data for tpy-DTTA4? and for the complexes. See http://www.rsc.org/suppdata/cc/b4/b400169a/
  作者：Robert Ruloff、Gerard van Koten、Andr� E. Merbach

  DOI：10.1039/b400169a

  日期：——

  [Fe(tpy-DTTA)2Gd2] is a self-assembled trinuclear complex based on a novel ligand in which a terpyridine and a poly(amino carboxylate) moiety are connected; it has a well-defined topology with favourable features to attain high relaxivities, i.e. a rigid FeII(tpy)2 core, reduced flexibility at the periphery thanks to a short linker, and efficient separation of the two GdIII centres.

  [Fe(tpy-DTTA)2Gd2]是一种基于新型配体的自组装三核复合物，其中联苯吡啶和聚（氨基羧酸）部分相连；它具有明确的拓扑结构，有利于实现高磁化率，即刚性FeII(tpy)2核心，由于短连接子而降低了外围的灵活性，以及两个GdIII中心的有效分离。