1,4,7,10-(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane | 174813-27-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,4,7,10-(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane
• 英文别名: 1,4,7,10-tetrakis(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane；1,4,7,10-tetra(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane；1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetrapropanenitrile；3-[4,7,10-tris(2-cyanoethyl)-1,4,7,10-tetrazacyclododec-1-yl]propanenitrile
• CAS: 174813-27-5
• 化学式: C₂₀H₃₂N₈
• 分子量: 384.528
• InChiKey: VABICLLBWZQBBK-UHFFFAOYSA-N

物化性质

• 沸点：
  655.0±55.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  108
• 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-(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane 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1,4,7,10-tetrakis(3-aminopropyl)-1,4,7,10-tetraazacyclododecane
  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
• 作为产物：
  描述：

  丙烯腈 、 轮环藤宁 以91%的产率得到1,4,7,10-(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane
  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

• Efficient Reduction of<i>tetrakis</i>(2‐Cyanoethyl)cyclen with Sodium–Toluene and Synthesis of Carboxymethyl‐ and Hydroxyethyl Functionalized Second Generation Pendant Arms Appended Cyclens
  作者：B. Jebasingh、V. Alexander

  DOI：10.1081/scc-200026243

  日期：2004.1

  1,4,7,10-tetrakis(2-Cyanoethyl)-1,4,7,10-tetraazacyclododecane (1) is efficiently reduced with sodium-toluene to give 1,4,7, 10-tetrakis(3-aminopropyl)-1,4,7,10-tetraazacyclododecane (2), which on alkylation affords carboxymethyl- and hydroxyethyl-functionalized second generation pendant ann appended cyclens, 1,4,7,10-tetrakis[N,N-bis (carboxymethyl)-3-propylamino]-1,4,7,10-tetraazacyclododecane (3), and 1,4,7,10-tetrakis[N,N-bis(2-hydroxyethyl)-3-propylamino]-1,4,7,10-tetraazacyclododecane (4).
• Synthesis, structural characterization of tetraazamacrocyclic ligand, five-coordinated zinc(II) complex
  作者：Deyuan Kong、Yuyuan Xie

  DOI：10.1016/s0020-1693(02)01025-3

  日期：2002.10

  1,4,7,10-tetrakis(2-cyanoethyl-)-1,4,7,10-tetraazacyclododecane(L) and Zn(1), Y(2), Er(3), Pr(4), Gd(5) complexes with L was synthesized and characterized. All metal complexes are in the general formula: [M(L)(H2O)](NO3)(2) (M = Zn, n = 1); and [M(L)(NO3)(2)]NO3.mH(2)O.nCH(3)CN (M = Y, Er, m = 5, n = 0; M = Pr, Gd, m = 0, n = 1, 1.5). Both ionic nitrate ion and bidentate coordinated nitrate ions are existed in complex 2-5. Structures of diprotonated L and zinc complexes were determined by X-ray diffraction. L was crystallized in diprotonated nitrate salt. In zinc complex, the central metal ion was coordinated with four nitrogen atoms of macrocyclic ligand and oxygen atom of water molecule, which defined a tetragonal pyramidal polyhedron. The bond lengths of Zn-N are in the range of 2.160(5)-2.177(6) Angstrom and the bond length of Zn-O is 1.918(4) Angstrom. (C) 2002 Elsevier Science B.V. All rights reserved.
• New tetraazamacrocyclic ligand with neutral pendent groups 1,4,7,10-tetrakis(2-cyanoethyl)-1,4,7,10-tetraazacyclododecane (L) and its cobalt(II), nickel(II) and copper(II) complexes: synthesis, structural characterization and antitumor activity
  作者：De-Yuan Kong*、Lin-Hua Meng、Jian Ding、Yu-Yuan Xie*、Xiao-Ying Huang

  DOI：10.1016/s0277-5387(99)00369-1

  日期：2000.1

  A new tetraazamacrocyclic ligand (L) with four neutral 2-cyanoethyl pendent groups, and its divalent transition-metal complexes [Co(L) (NO3)]NO3 . H2O (1), [Ni(L) (NO3)]NO3 . 3H(2)O (2) and [Cu(L) (H2O)] (NO3)(2) (3) have been synthesized. The crystal structures of 1 and 3 have been determined by X-ray analysis. In complex 1 the cobalt atom is coordinated by four nitrogen atoms and two oxygen atoms of a nitrate anion, which define a distorted octahedron. The other nitrate ion lies in the lattice as a counter ion. Complex 3 is five-coordinated by four nitrogen atoms and an axial aqua ligand, which form a tetragonal pyramid. In complex 3 the two nitrate anions exist as counter ions. Pharmaceutical tests showed that all three metal complexes exhibit antitumor activity against HL-60 and BEL-7404 tumor cell lines in vitro, even at a concentration of 10(-8) mol l(-1). Complex 1 can partially cleave supercoiled pBR 322 DNA to form nicked DNA in aerobic solution, and complex 3 can convert double strand DNA into nicked DNA completely in the presence of MPA. Complex 3 causes perturbation to K562 tumor cell lines in the G(1) phase. (C) 2000 Elsevier Science Ltd All rights reserved.