2,8,14,20,25,26,27,28-Octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene | 1195970-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,8,14,20,25,26,27,28-Octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 1195970-74-1
• 化学式: C₂₀H₁₆N₈
• 分子量: 368.401
• InChiKey: MZBUZIAULLUCME-UHFFFAOYSA-N

物化性质

• 熔点：
  297-298 °C(Solv: acetone (67-64-1))
• 沸点：
  908.5±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,8,14,20,25,26,27,28-Octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene 、 3,4,5-tristetradecyloxybenzyl bromide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以54%的产率得到2,8,14,20-Tetrakis[[3,4,5-tri(tetradecoxy)phenyl]methyl]-2,8,14,20,25,26,27,28-octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
  参考文献：
  名称：

  液晶大环azacalix [4]吡啶及其与锌离子的络合物：从鞍形到扁平形的构象变化。

  摘要：

  具有马鞍形核的azacalix [4]吡啶（1）取代了四个3,4,5-三（烷氧基）苄基迷你树枝状结构，是杂芳烃的第一个液晶（LC）。通过与锌离子络合，构象调节氮杂杯[4]吡啶导致LC特性发生重大变化。

  DOI：

  10.1039/c5cc01018g
• 作为产物：
  描述：

  2,8,14,20-Tetrakis(prop-2-enyl)-2,8,14,20,25,26,27,28-octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene 在 potassium tert-butylate 、 盐酸 作用下， 以 二甲基亚砜 、 水 、 丙酮 为溶剂， 反应 2.0h， 以98%的产率得到2,8,14,20,25,26,27,28-Octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
  参考文献：
  名称：

  Synthesis of (NH)_m(NMe)_4−m-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties

  摘要：

  The (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.

  DOI：

  10.1021/jo901609u

文献信息

• Proton-Assisted Reduction of CO₂ by Cobalt Aminopyridine Macrocycles
  作者：Alon Chapovetsky、Thomas H. Do、Ralf Haiges、Michael K. Takase、Smaranda C. Marinescu

  DOI：10.1021/jacs.6b01980

  日期：2016.5.11

  efficient reduction of CO2 to CO by cobalt aminopyridine macrocycles. The effect of the pendant amines on catalysis was investigated. Several cobalt complexes based on the azacalix[4](2,6)pyridine framework with different substitutions on the pendant amine groups have been synthesized (R = H (1), Me (2), and allyl (3)), and their electrocatalytic properties were explored. Under an atmosphere of CO2 and in

  我们在这里报告了钴氨基吡啶大环化合物将 CO2 有效还原为 CO。研究了侧链胺对催化的影响。已经合成了几种基于氮杂杯[4](2,6)吡啶骨架在侧胺基上具有不同取代基的钴配合物(R = H(1)、Me(2)和烯丙基(3))，及其电催化性能进行了探索。在 CO2 气氛和弱布朗斯台德酸存在下，观察到大催化电流 1，对应于 CO2 还原为 CO，法拉第效率 (98 ± 2%)。相比之下，配合物 2 和 3 产生的 CO 的 TON 至少比 1 低 300 倍，这表明仲胺的侧链 NH 部分的存在对催化至关重要。而且，
• Synthesis of (NH)_<i>m</i>(NMe)_4−<i>m</i>-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties
  作者：En-Xuan Zhang、De-Xian Wang、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo901609u

  日期：2009.11.20

  The (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.
• Liquid crystalline macrocyclic azacalix[4]pyridine and its complexes with the zinc ion: conformational change from the saddle to flattened shape
  作者：Shi-Xin Fa、Xiao-Fang Chen、Shuang Yang、De-Xian Wang、Liang Zhao、Er-Qiang Chen、Mei-Xiang Wang

  DOI：10.1039/c5cc01018g

  日期：——

  Substituted with four 3,4,5-tris(alkoxy)benzyl mini-dendrons, azacalix[4]pyridine (1) with the saddle-shaped core is the first liquid crystal (LC) of heteracalixaromatics. Conformational regulation of azacalix[4]pyridine by complexing with the zinc ion leads to a significant change in LC properties.

  具有马鞍形核的azacalix [4]吡啶（1）取代了四个3,4,5-三（烷氧基）苄基迷你树枝状结构，是杂芳烃的第一个液晶（LC）。通过与锌离子络合，构象调节氮杂杯[4]吡啶导致LC特性发生重大变化。