NPS 383 | 87955-89-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: NPS 383
• 英文别名: N,N′,N″,N'''-tetrakis(2-cyanoethyl)-1,4,8,11-tetraazacyclotetradecane；N,N',N'',N'''-tetra(3-aminopropyl)-1,4,8,11-tetra-azacyclotetradecane；1,4,8,11-(3-aminopropyl)-1,4,8,11-tetraazacyclotetradecane；3-[4,8,11-Tris(3-aminopropyl)-1,4,8,11-tetrazacyclotetradec-1-yl]propan-1-amine
• CAS: 87955-89-3
• 化学式: C₂₂H₅₂N₈
• 分子量: 428.708
• InChiKey: ASQWRCDZJRABBG-UHFFFAOYSA-N

物化性质

• 沸点：
  576.6±50.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  水杨醛 、 NPS 383 以 甲苯 为溶剂， 反应 72.0h， 以78%的产率得到2-[3-[4,8,11-Tris[3-[(2-hydroxyphenyl)methylideneamino]propyl]-1,4,8,11-tetrazacyclotetradec-1-yl]propyliminomethyl]phenol
  参考文献：
  名称：

  A novel nickel (II) complex based on a cyclam-cored generation-one dendrimeric salicylaldimine ligand and its application as a catalyst precursor in norbornene polymerization: Comparative study with some other first generation DAB-polypropyleneimine metallodendrimers

  摘要：

  A new cyclam based first generation metallodendrimer with nickel centres on the periphery as well as at the core was synthesized by reacting a novel tetrakis(salicylaldimine) cyclam ligand with nickel acetate. The trinuclear complex was evaluated as a catalyst precursor in the vinyl polymerization of norbornene using methylaluminoxane as co-catalyst. The activity of this cyclam-based complex was compared with that of first generation DAB-PPI-salicylaldimine and DAB-PPI-pyridine-imine complexes (DAB = diaminobutane, PPI = polypropyleneimine). The cyclam based complex was found to have superior activity than both the DAB-PPI analogues as well as analogous mononuclear complexes. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.015
• 作为产物：
  描述：

  NN^,N^,,N^,,,-tetra(2-cyanoethyl)-1,4,8,11-tetra-azacyclo-tetradecane 在 sodium hydroxide 、 氢气 、 镍 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以58%的产率得到NPS 383
  参考文献：
  名称：

  迈克尔加成法合成 N,N',N",N"'-Tetra-(2-carboxyethyl)-和 N,N',N",N"'-Tetra-(3-aminopropyl)-tetraazacycloalkanes多氮杂环烷烃制备丙烯酸和丙烯腈

  摘要：

  摘要 报道了一种顺利、方便地一步合成 N,N',N",N"'-四-(2-羧乙基)-四氮杂环烷烃的方法。这些化合物是通过四氮杂环烷烃与丙烯酸的迈克尔加成合成的。四氮杂环烷烃与过量丙烯腈的相同迈克尔加成也产生相应的四氰乙基化衍生物。此类四氰乙基化化合物的还原是制备相应伯胺的新途径。

  DOI：

  10.1080/00397919608003860

文献信息

• Chemistry of structurally developed macrocycles. Part 2. Synthesis and complexing properties of N,N′,N″,N‴-tetra(3-aminopropyl)-1,4,8,11-tetra-azacyclotetradecane with nickel(<scp>II</scp>)
  作者：Kevin P. Wainwright

  DOI：10.1039/dt9830001149

  日期：——

  11-tetraazacyclotetradecane in high yield. Complexation of this ligand with nickel(II) under neutral conditions leads to high-spin five-co-ordinate species in which the co-ordination occurs via the four tertiary amine nitrogen atoms and one of the pendant primary amine nitrogen atoms, irrespective of the nature of the anion. Further nickel may also be co-ordinated by the other three primary amine nitrogen

  的还原Ñ，Ñ '，Ñ “，Ñ ''' -四（2-氰基乙基）-1,4,8,11-四azacyclotetradecane在甲苯钠和乙醇生成辛胺Ñ，Ñ '，Ñ ”，N ‴-四（3-氨基丙基）-1,4,8,11-四氮杂环十四烷高产率。在中性条件下该配体与镍（II）的络合导致高纺丝五配位物质，其中配位通过不论阴离子的性质如何，四个叔胺氮原子和一个悬垂的伯胺氮原子之一。另外的镍也可以被其他三个伯胺氮原子配位，从而产生聚合物产物。四个侧基胺基团的选择性质子化反应可在乙醇中可逆地完成，而不会破坏络合物。该质子化的伯胺基团用于稳定弱供体的阴离子如CLO的协调4 -，BF 4 - ，和HSO 4 -在轴向协调位置，导致各种五坐标复合体。镍的自旋态取决于轴向基团的配体场强，在从溴化物变为氯化物时观察到从低自旋到高自旋的交叉。就轴向配体场强度而言，交叉的方向表示这些化合物的正方形-锥体结构，而不是三角形-双锥体结构。
• A New Versatile Synthesis of N,N′,N″,N″′-Tetra-(2-carboxyethyl)-and N,N′,N″,N″′-Tetra-(3-aminopropyl)-tetraazacycloalkanes by Michael Addition of Polyazacycloalkanes to Acrylic Acid and Acrylonitrile
  作者：C. Gros、H. Chollet、A. K. Mishra、R. Guilard

  DOI：10.1080/00397919608003860

  日期：1996.1

  convenient one step synthesis of N,N′,N″,N″′-tetra-(2-carboxyethyl)-tetraazacycloalkanes is reported. These compounds are synthesized by Michael addition of tetraazacycloalkanes to acrylic acid. The same Michael addition of tetraazacycloalkanes to an excess of acrylonitrile also leads to the corresponding tetracyanoethylated derivatives. The reduction of such tetracyanoethylated compounds is a new way of preparation

  摘要 报道了一种顺利、方便地一步合成 N,N',N",N"'-四-(2-羧乙基)-四氮杂环烷烃的方法。这些化合物是通过四氮杂环烷烃与丙烯酸的迈克尔加成合成的。四氮杂环烷烃与过量丙烯腈的相同迈克尔加成也产生相应的四氰乙基化衍生物。此类四氰乙基化化合物的还原是制备相应伯胺的新途径。
• A novel nickel (II) complex based on a cyclam-cored generation-one dendrimeric salicylaldimine ligand and its application as a catalyst precursor in norbornene polymerization: Comparative study with some other first generation DAB-polypropyleneimine metallodendrimers
  作者：Rehana Malgas-Enus、Selwyn F. Mapolie

  DOI：10.1016/j.poly.2012.08.015

  日期：2012.10

  A new cyclam based first generation metallodendrimer with nickel centres on the periphery as well as at the core was synthesized by reacting a novel tetrakis(salicylaldimine) cyclam ligand with nickel acetate. The trinuclear complex was evaluated as a catalyst precursor in the vinyl polymerization of norbornene using methylaluminoxane as co-catalyst. The activity of this cyclam-based complex was compared with that of first generation DAB-PPI-salicylaldimine and DAB-PPI-pyridine-imine complexes (DAB = diaminobutane, PPI = polypropyleneimine). The cyclam based complex was found to have superior activity than both the DAB-PPI analogues as well as analogous mononuclear complexes. (c) 2012 Elsevier Ltd. All rights reserved.