1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane | 136599-72-9

• 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: 1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane
• 英文别名: N,N-diethyl-2-[4,7,10-tris[2-(diethylamino)-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide
• CAS: 136599-72-9
• 化学式: C₃₂H₆₄N₈O₄
• 分子量: 624.911
• InChiKey: ILLSOVLAHOCJHO-UHFFFAOYSA-N

物化性质

• 沸点：
  738.1±60.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane 、 terbium(III) trifluoromethanesulfonate 以 乙腈 为溶剂， 生成 [Tb(1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane)](CF₃SO₃)3
  参考文献：
  名称：

  Analyzing Lanthanide-Induced Shifts in the NMR Spectra of Lanthanide(III) Complexes Derived from 1,4,7,10-Tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane

  摘要：

  Variable-temperature H-1 and C-13 NMR spectra have been obtained for solutions of lanthanide(III) complexes derived from 1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane in deuterated acetonitrile. The lanthanide-induced shifts (LIS) observed in the spectra of the paramagnetic complexes (Ln = Pr, Nd, Sm, Eu, Tb, Dy, Ho, Er, Tm, and Yb) are analyzed using a linear least-squares procedure involving the five componenents of the traceless part of the magnetic susceptibility tenser as fitting parameters (C-13 data is limited to Ln = Pr, Nd, Sm, and Eu). No assumptions are made regarding the orientation of the molecular coordinate system and principal magnetic axis system in this method of analysis. Furthermore, by using a linear least-squares fitting of the data, we establish that it is possible to allow a computer program to permute LIS values over any number of nuclei and determine which particular assignment gives the best fit of the LIS data. A new method of evaluating the contact component of the LIS in the proton spectra is introduced. Molecular mechanics calculations are combined with analyses of LIS data to determine structures of the complexes in solution. Through such an approach, we establish that the eight-coordinate lanthanide ions are encapsulated by the octadentate macrocyclic ligand, with the four nitrogen atoms and four oxygen atoms situated at the vertices of a distorted square antiprism having C-4 symmetry (the rotational angle between the two square pyramids is 47 degrees). The lanthanide ions lie above the plane of nitrogen atoms of the macrocycle, with the distance decreasing from 1.74 to 1.41 Angstrom across the lanthanide series. The distance to the mean plane of donor oxygen atoms increases from 0.63 to 0.83 Angstrom across the series. The Ln(3+)-N and Ln(3+)-O bond distances range from 2.82 to 2.54 Angstrom and 2.47 to 2.21 Angstrom, respectively. The NMR data establish that each complex exists in solution as a single pair of enantiomers. Analysis of the LIS data establishes that the isomer with each ethylenediamine ring of the macrocycle in the lambda conformation with clockwise rotation of the pendant arms, or its enantiomer, is favored in solution.

  DOI：

  10.1021/ic00118a018
• 作为产物：
  描述：

  1,4,7,10-tetraazacyclododecane tetrahydrochloride 、 N,N-二乙基-2-氯乙酰胺 以40%的产率得到1,4,7,10-tetrakis(N,N-diethylacetamido)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Multiarmed macrocyclic polyamines exhibiting unique cation-binding and cation-transport properties toward alkali-metal and alkaline-earth-metal cations

  摘要：

  A variety of multiarmed macrocyclic polyamines were prepared as a new type of metal carrier, in which amide-, ester-, nitrile-, and ketone-functionalized arms were attached as secondary donor sites. Extraction and C-13 NMR binding experiments revealed that their cation-binding behavior was largely dependent on the nature of the arm donor group as well as the size of the parent polyamine ring. In particular, introduction of an amide-functionalized arm into a suitable polyamine ring significantly enhanced binding ability toward "hard" metal cations, while the parent polyamine ring weakly bound these metal cations. Their unique cation-binding properties offered an effective membrane transport of hard metal cations. Since the cation-binding and -transport profiles of the new multiarmed macrocyclic polyamines differed greatly from those observed with conventional polyamines and related macrocycles, the present study provides a new possibility for designing a novel, macrocyclic polyamine type of synthetic carrier.

  DOI：

  10.1021/jo00025a028