3,9-Bis(tert-butoxycarbonylmethyl)-6-benzyloxycarbonyl-3,6,9-triazaundecanedicarboxylic acid-di-tert-butyl ester | 178552-54-0

• 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: 3,9-Bis(tert-butoxycarbonylmethyl)-6-benzyloxycarbonyl-3,6,9-triazaundecanedicarboxylic acid-di-tert-butyl ester
• 英文别名: tert-butyl 2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl-phenylmethoxycarbonylamino]ethyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]acetate
• CAS: 178552-54-0
• 化学式: C₃₆H₅₉N₃O₁₀
• 分子量: 693.879
• InChiKey: CKZYDSBFGVYKIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3,9-Bis(tert-butoxycarbonylmethyl)-6-benzyloxycarbonyl-3,6,9-triazaundecanedicarboxylic acid-di-tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 DTTA
  参考文献：
  名称：

  苯核三核GdIII配合物：朝着在高磁场下MRI造影剂应用的松弛度优化的方向发展。

  摘要：

  基于带有三个亚甲基二亚乙基三胺-N，N，N''，N''-四乙酸酯部分（-CH（2）DTTA（4-））的Gd（3+）的三甲苯基的新型配体H（12）L ）螯合物已经合成，其三核Gd（3+）配合物[Gd（3）L（H（2）O）（6）]（3-）就MRI造影剂的应用进行了研究。在[Gd（3）L（H（2）O）（6）]（3-）上进行的多场可变温度（17）O NMR和质子弛豫研究得出了表征水交换和旋转动力学的参数。基于（17）O化学位移，可以证明Gd（3+）的二水合。水交换率k（ex）（298）= 9.0 +/- 3.0 s（-1）大约是商品[Gd（DTPA）（H（2）O）的k（ex）（298）的两倍）]（2-），与类似的Gd（3 +）-DTTA螯合物相当。尽管综合体的规模相对较小，旋转动力学必须用Lipari-Szabo方法描述，将整体运动与局部运动分开。局部和全局旋转相关时间之间的差异分别为tau（10）（298）=

  DOI：

  10.1039/b717390c
• 作为产物：
  描述：

  1,7-Bis(trifluoroacetyl)-4-benzyloxycarbonyl-1,4,7-triazaheptane 在 乙醇 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,9-Bis(tert-butoxycarbonylmethyl)-6-benzyloxycarbonyl-3,6,9-triazaundecanedicarboxylic acid-di-tert-butyl ester
  参考文献：
  名称：

  Dynamic aggregation of the mid-sized gadolinium complex {Ph4[Gd(DTTA)(H2O)2]− 3}

  摘要：

  A compound binding three Gd3+ ions, {Ph-4[Gd(DTTA)(H2O)(2)](-) (3)} (where H(5)DTTA is diethylenetriaminetetraacetic acid), has been synthesized around a hydrophobic center made up of four phenyl rings. In aqueous solution the molecules start to self-aggregate at concentrations well below 1 mM as shown by the increase of rotational correlation times and by the decrease of the translational self-diffusion constant. NMR spectra recorded in aqueous solution of the diamagnetic analogue {Ph-4[Y(DTTA)(H2O)(2)](-) (3)} show that the aggregation is dynamic and due to intermolecular pi-stacking interactions between the hydrophobic aromatic centers. From estimations of effective radii, it can be concluded that the aggregates are composed of two to three monomers. The paramagnetic {Ph-4[Gd(DTTA)(H2O)(2)](-) (3)} exhibits concentration-dependent H-1 NMR relaxivities with high values of approximately 50 mM(-1) s(-1) (30 MHz, 25 A degrees C) at gadolinium concentrations above 20 mM. A combined analysis of H-1 NMR dispersion profiles measured at different concentrations of the compound and O-17 NMR data measured at various temperatures was performed using different theoretical approaches. The fitted parameters showed that the increase in relaxivity with increasing concentration of the compound is due to slower global rotational motion and an increase of the Lipari-Szabo order parameter S-2.

  DOI：

  10.1007/s00775-013-1036-y

文献信息

• A benzene-core trinuclear Gd^IIIcomplex: towards the optimization of relaxivity for MRI contrast agent applications at high magnetic field
  作者：João Bruno Livramento、Lothar Helm、Angélique Sour、Conlin O'Neil、André E. Merbach、Éva Tóth

  DOI：10.1039/b717390c

  日期：——

  A novel ligand, H(12)L, based on a trimethylbenzene core bearing three methylenediethylenetriamine-N,N,N'',N''-tetraacetate moieties (-CH(2)DTTA(4-)) for Gd(3+) chelation has been synthesized, and its trinuclear Gd(3+) complex [Gd(3)L(H(2)O)(6)](3-) investigated with respect to MRI contrast agent applications. A multiple-field, variable-temperature (17)O NMR and proton relaxivity study on [Gd(3)L(H(2)O)(6)](3-)

  基于带有三个亚甲基二亚乙基三胺-N，N，N''，N''-四乙酸酯部分（-CH（2）DTTA（4-））的Gd（3+）的三甲苯基的新型配体H（12）L ）螯合物已经合成，其三核Gd（3+）配合物[Gd（3）L（H（2）O）（6）]（3-）就MRI造影剂的应用进行了研究。在[Gd（3）L（H（2）O）（6）]（3-）上进行的多场可变温度（17）O NMR和质子弛豫研究得出了表征水交换和旋转动力学的参数。基于（17）O化学位移，可以证明Gd（3+）的二水合。水交换率k（ex）（298）= 9.0 +/- 3.0 s（-1）大约是商品[Gd（DTPA）（H（2）O）的k（ex）（298）的两倍）]（2-），与类似的Gd（3 +）-DTTA螯合物相当。尽管综合体的规模相对较小，旋转动力学必须用Lipari-Szabo方法描述，将整体运动与局部运动分开。局部和全局旋转相关时间之间的差异分别为tau（10）（298）=
• Cu²⁺-Responsive Bimodal (Optical/MRI) Contrast Agent for Cellular Imaging
  作者：Joo Hee Jang、Sankarprasad Bhuniya、Jongeun Kang、Areum Yeom、Kwan Soo Hong、Jong Seung Kim

  DOI：10.1021/ol4025293

  日期：2013.9.20

  A water-soluble T-1 magnetic resonance imaging contrast agent (1) has been synthesized. The bimodal contrast agent 1 responds to the Cu2+ ion in living cells by enhancing the MRI modality signal whereas the optical signal gradually drops. This dual modality probe response depends on the cellular free copper ions in RAW 264.7 cells even at the micromolar level.
• Dynamic aggregation of the mid-sized gadolinium complex {Ph4[Gd(DTTA)(H2O)2]− 3}
  作者：Hugues Jaccard、Pascal Miéville、Caroline Cannizzo、Cédric R. Mayer、Lothar Helm

  DOI：10.1007/s00775-013-1036-y

  日期：2014.2

  A compound binding three Gd3+ ions, Ph-4[Gd(DTTA)(H2O)(2)](-) (3)} (where H(5)DTTA is diethylenetriaminetetraacetic acid), has been synthesized around a hydrophobic center made up of four phenyl rings. In aqueous solution the molecules start to self-aggregate at concentrations well below 1 mM as shown by the increase of rotational correlation times and by the decrease of the translational self-diffusion constant. NMR spectra recorded in aqueous solution of the diamagnetic analogue Ph-4[Y(DTTA)(H2O)(2)](-) (3)} show that the aggregation is dynamic and due to intermolecular pi-stacking interactions between the hydrophobic aromatic centers. From estimations of effective radii, it can be concluded that the aggregates are composed of two to three monomers. The paramagnetic Ph-4[Gd(DTTA)(H2O)(2)](-) (3)} exhibits concentration-dependent H-1 NMR relaxivities with high values of approximately 50 mM(-1) s(-1) (30 MHz, 25 A degrees C) at gadolinium concentrations above 20 mM. A combined analysis of H-1 NMR dispersion profiles measured at different concentrations of the compound and O-17 NMR data measured at various temperatures was performed using different theoretical approaches. The fitted parameters showed that the increase in relaxivity with increasing concentration of the compound is due to slower global rotational motion and an increase of the Lipari-Szabo order parameter S-2.