N,N'-bis(4-pyridylmethyl)diaza-18-crown-6 | 130985-62-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(4-pyridylmethyl)diaza-18-crown-6
• 英文别名: N,N'-bis(4-pyridylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclododecane；7,16-Bis(pyridin-4-ylmethyl)-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
• CAS: 130985-62-5
• 化学式: C₂₄H₃₆N₄O₄
• 分子量: 444.574
• InChiKey: NFIUTPMTFOYIEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  63.0-64.0 °C(Solv: heptane (142-82-5))
• 沸点：
  597.0±45.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氯甲基吡啶盐酸盐 、 二氮杂18-冠醚-6 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以72%的产率得到N,N'-bis(4-pyridylmethyl)diaza-18-crown-6
  参考文献：
  名称：

  Pyridine-armed diaza-crown ethers: molecular design of effective synthetic ionophores

  摘要：

  A variety of double-armed diaza-crown ethers were examined as synthetic ionophores in which pyridine- and quinoline-functionalized arms were attached as secondary donor sites. Binding constant determinations and C-13 NMR titration experiments revealed that introduction of a pyridine-functionalized arm, if in the proper geometrical arrangement, significantly enhanced complex stabilities for divalent metal cations via three-dimensional encapsulation. In a CH2Cl2 liquid membrane transport system, some pyridine-armed diaza-crown ethers exhibited unique and excellent transport abilities for transition-metal cations as well as for alkali and alkaline earth cations. Since these transport profiles differed greatly from those observed with conventional crown ethers, the present study offers new possibilities for designing novel types of synthetic ionophores.

  DOI：

  10.1021/jo00001a051

文献信息

• Pyridino-armed diaza-crown ethers for specific transport of “transition metal cations”
  作者：Hiroshi Tsukube、Kouichi Yamashita、Tadashi Iwachido、Michio Zenki

  DOI：10.1016/s0040-4039(00)80152-5

  日期：——

  A new series of double armed diaza-crown ethers, bearing pyridino- and quinolino-arm groups, were first shown to effectivelybind and transport some “transition metal cations” via three-dimensional complexations, which were not attained by common crown ethers.

  一系列新的带有吡啶基和喹啉基-臂基团的重氮二氮杂-冠醚首先被证明可以通过三维络合物有效地结合和运输一些“过渡金属阳离子”，而这是普通冠醚无法达到的。
• Syntheses of armed-macrocycles by reductive amination using NaBH(OAc)₃under 1 MPa
  作者：Yoichi Habata、Futoshi Osaka、Sachiko Yamada

  DOI：10.1002/jhet.5570430123

  日期：2006.1

  monoaza-15-crown-5, diaza-12-crown-4, diaza-18-crown-6 ethers, and 1,4,7,10-tetraazacyclododecane having aromatic pendants were prepared by the reductive amination of the corresponding macrocycles with aromatic carboxyaldehydes in the presence of NaBH(OAc)3. Reductive amination under 1 MPa conditions provided significant shortening of the reaction time and yield enhancements.

  制备了具有芳香族侧基的武装单氮杂12-冠-4，单氮杂15-冠-5，二氮杂12-冠-4，二氮杂18-冠-6醚和1,4,7,10-四氮杂环十二烷通过在NaBH（OAc）3存在下用芳族羧醛对相应的大环化合物进行还原胺化来实现。在1 MPa条件下进行还原胺化可显着缩短反应时间并提高收率。