2,8-Dimethyl-14,20-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(27),10,12,15,17,19(26),21,23-dodecaene | 1195970-67-2

• 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-Dimethyl-14,20-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(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 1195970-67-2
• 化学式: C₂₈H₂₈N₈
• 分子量: 476.584
• InChiKey: ZZTXQPRWLXXTQM-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：

  2,8-Dimethyl-14,20-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(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100%的产率得到14,20-Dimethyl-2,8,14,20,25,26,27,28-octazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),2,4,6,8,10,12,15(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
• 作为产物：
  描述：

  N2，N6-二（6-溴代吡啶-2-基）-N2，N6-二甲基吡啶-2,6-二胺 、 2,6-bis(allylamino)pyridine 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2,8-Dimethyl-14,20-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(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