2,14-Dimethyl-8,20-bis(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),4,6,9,11,13(27),15(26),16,18,21,23-dodecaene | 1195970-66-1

• 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: 2,14-Dimethyl-8,20-bis(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),4,6,9,11,13(27),15(26),16,18,21,23-dodecaene
• CAS: 1195970-66-1
• 化学式: C₂₈H₂₈N₈
• 分子量: 476.584
• InChiKey: AUZYFZKAALYPRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,14-Dimethyl-8,20-bis(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),4,6,9,11,13(27),15(26),16,18,21,23-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100%的产率得到2,14-Dimethyl-2,8,14,20,25,26,27,28-octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9(27),10,12,15,17,19(26),21(25),22-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
• 作为产物：
  描述：

  N-allyl-bis(6-bromopyridin-2-yl)amine 、 N2,N2'-(pyridine-2,6-diyl)-bis(N2,N6-dimethylpyridine-2,6-diamine) 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,3-双(二苯基膦)丙烷 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以36%的产率得到2,14-Dimethyl-8,20-bis(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),4,6,9,11,13(27),15(26),16,18,21,23-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

• Synthesis and structure of N-methylated azacalix[4]pyridines and azacalix[1]arene[3]pyridines
  作者：Jiang-Tao Li、Yu-Fei Ao、Qi-Qiang Wang、De-Xian Wang、Mei-Xiang Wang

  DOI：10.1016/j.tetlet.2017.08.024

  日期：2017.9

  Reaction of azacalix[4]pyridine and azacalix[1]arene[3]pyridine with methyl iodide afforded N-methylated products selectively and highly efficiently. Crystal structures revealed that the modified electronic nature of the pyridines could change the conjugation between the bridging nitrogen and the neighbouring aromatics.

  氮杂杯[4]吡啶和氮杂杯[1]芳烃[3]吡啶与碘代甲烷的反应选择性地和高效地提供了N-甲基化产物。晶体结构表明，吡啶的修饰电子性质可以改变桥联氮与相邻芳族化合物之间的共轭。
• 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.