N,N'-bis(cyanomethyl)-4,13-diaza-18-crown-6 | 120129-34-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(cyanomethyl)-4,13-diaza-18-crown-6
• 英文别名: 2-[16-(Cyanomethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]acetonitrile
• CAS: 120129-34-2
• 化学式: C₁₆H₂₈N₄O₄
• 分子量: 340.423
• InChiKey: ATOJSDFYKAFFNY-UHFFFAOYSA-N

物化性质

• 沸点：
  519.6±50.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis(cyanomethyl)-4,13-diaza-18-crown-6 在 sodium 作用下， 以 甲醇 为溶剂， 生成 C₁₆H₂₈N₄O₄*Na⁽¹⁺⁾
  参考文献：
  名称：

  ，具有pi-donor-group-sidearms的'，（-被取代）-4,13-diaza-18-crown-6衍生物：热力学与固态结构的相关性

  摘要：

  溶液热力学数据和固态结构信息用于显示一系列，“ - （取代的）-4,13二氮杂-18-冠醚-6（圣经）缺乏氧或氮供体基团在腰佩不衍生物利用侧臂进行结合，但结合常数显示出相当大的变化。

  DOI：

  10.1016/0040-4039(88)85076-7
• 作为产物：
  描述：

  C₁₆H₂₈N₄O₄*Na⁽¹⁺⁾ 以 甲醇 为溶剂， 生成 N,N'-bis(cyanomethyl)-4,13-diaza-18-crown-6
  参考文献：
  名称：

  ，具有pi-donor-group-sidearms的'，（-被取代）-4,13-diaza-18-crown-6衍生物：热力学与固态结构的相关性

  摘要：

  溶液热力学数据和固态结构信息用于显示一系列，“ - （取代的）-4,13二氮杂-18-冠醚-6（圣经）缺乏氧或氮供体基团在腰佩不衍生物利用侧臂进行结合，但结合常数显示出相当大的变化。

  DOI：

  10.1016/0040-4039(88)85076-7

文献信息

• Influence of pendant cyanoalkyl side-arms on the stabilities of metal ion complexes of monoaza- and diaza-18-crown-6 ethers in methanol
  作者：J. Stroka、T. Ossowski、B.G. Cox、A. Thaler、H. Schneider

  DOI：10.1016/0020-1693(94)03811-2

  日期：1994.5

  Abstract Pendant cyanomethyl and 2-cyanoethyl arms attached to the nitrogen atoms of aza-crown ligands can influence complex stabilities with metal ions in methanol in two distinct ways: by reducing the basicities of the ring nitrogen atoms, and by disrupting the solvation of the ligands and complexes. In Ag + complexes, and probably also in Zn 2+ , Cd 2+ and Pb 2+ complexes, the dominant effect is

  摘要连接在氮杂冠配体氮原子上的侧基氰甲基和2-氰乙基臂可通过两种不同的方式影响金属离子在甲醇中的复杂稳定性：降低环氮原子的碱度和破坏配体的溶剂化和复合体。在Ag +络合物中，也可能在Zn 2+，Cd 2+和Pb 2+络合物中，主要作用是氮碱性的降低，导致在氰基烷基臂存在下稳定性的净降低。然而，碱金属离子络合物的稳定性常数增加，主要因素是未络合的取代大环化合物相对于专利配体A18C6和A 2 18C6在甲醇中的溶剂化较差。对于碱土配合物，金属配合物减少的溶剂化对游离配体溶剂化的影响被过度补偿；侧臂可防止甲醇分子对络合的阳离子进行配位，从而降低络合物的稳定性。在任何情况下，都没有任何证据表明金属离子与氰基烷基侧链之间存在直接相互作用。
• Molecular Boxes Derived from Crown Ethers and Nucleotide Bases: Probes for Hoogsteen vs Watson-Crick H-Bonding and Other Base-Base Interactions in Self-Assembly Processes
  作者：Otto F. Schall、George W. Gokel

  DOI：10.1021/ja00093a005

  日期：1994.7

  Bibracchial lariat ethers based upon 4, 13-diaza-18-crown-6 having -(CH2)(3)-sidearms terminated in adenine or thymine have been prepared and characterized. The three structures are as follows: adenine-(CH2)(3)-(N18N)(CH2)(3)-adenine (A-O-A), thymine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (T-O-T), and adenine-(CH2)(3)-(N18N)-(CH2)(3)-thymine (A-O-T). Association of the nucleotide bases was expected to afford molecular boxes or other aggregates that would be stabilized by interactions between or among the nucleotide bases. These compounds have been studied in solution by H-1-NMR spectroscopy and by vapor pressure osmometry to determine the extent of association as well as what interactions occur between the bases. The H-1-NMR solution studies involved both temperature and concentration dependence and NOE studies. Several lines of evidence make clear that association does occur in CDCl3 with an association constant for A-O-A with T-O-T of 855 M(-1). Both intra- and intermolecular H-bonding interactions are detected. Hoogsteen binding modes appear to play a very important role in these flexible systems. The A-O-A.T-O-T box may also comprise a ditopic receptor system in which the sides of the box are Ade::Thy pairs and the ends are crown ethers. We have studied such systems in the presence of decanediyldiammonium and dodecanediyldiammonium salts and report evidence for a ternary induced-fit receptor complex.
• The crystal structure of N,N′-bis(cyanomethyl)- 1,10-diaza-4,7,13,16-tetraoxa-cyclooctadecane rubidium iodide hydrate
  作者：Gabriela Weber、Wolfram Saenger、Klaus Müller、Winfried Wehner、Fritz Vögtle

  DOI：10.1016/s0020-1693(00)82613-4

  日期：1983.1
• ,'-(subst1tuted)-4,13-diaza-18-crown-6 derivatives having pi-donor-group-sidearms: correlation of thermodynamics and solid state structures
  作者：Kristin A Arnold、Anthony M Viscariello、MinSook Kim、Richard D Gandour、Frank R Fronczek、George W Gokel

  DOI：10.1016/0040-4039(88)85076-7

  日期：1988.1

  Solution thermodynamic data and solid state structure information are used to show that a series of ,'-(substituted)-4,13-diaza-18-crown-6 (BiBLE) derivatives which lack oxygen or nitrogen donor groups in the sidearms do not utilize the sidearms for binding but show considerable variation in their binding constants.

  溶液热力学数据和固态结构信息用于显示一系列，“ - （取代的）-4,13二氮杂-18-冠醚-6（圣经）缺乏氧或氮供体基团在腰佩不衍生物利用侧臂进行结合，但结合常数显示出相当大的变化。