10,22-Bis-(4-bromo-phenyl)-1,4,7,13,16,19-hexaoxa-10,22-diaza-cyclotetracosane | 667419-56-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 10,22-Bis-(4-bromo-phenyl)-1,4,7,13,16,19-hexaoxa-10,22-diaza-cyclotetracosane
• 英文别名: 10,22-Bis(4-bromophenyl)-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane；10,22-bis(4-bromophenyl)-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane
• CAS: 667419-56-9
• 化学式: C₂₈H₄₀Br₂N₂O₆
• 分子量: 660.443
• InChiKey: DXASSUWPUINRSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  吗啉 、 10,22-Bis-(4-bromo-phenyl)-1,4,7,13,16,19-hexaoxa-10,22-diaza-cyclotetracosane 在 palladium diacetate 三叔丁基膦 、 sodium t-butanolate 作用下， 以78%的产率得到10,22-Bis-(4-morpholin-4-yl-phenyl)-1,4,7,13,16,19-hexaoxa-10,22-diaza-cyclotetracosane
  参考文献：
  名称：

  Substituent effects in the binding of bis(4-fluorobenzyl)ammonium ions by dianilino[24]crown-8

  摘要：

  A series of para-substituted dianilino[24]crown-8 (DA24C8) macrocycles were synthesized and their ability to form host-guest complexes with bis(4-fluorobenzyl)ammonium ions (DFA(+)) were investigated. Although these crown ethers contain weakly hydrogen bonding aniline motifs, they do bind DFA(+) in CDCl3/CD3NO2 solution, presumably in a pseudo rotaxane-like manner. A plot of the values of the relative binding strengths (log[K-a(R)/K-a(H)]) versus the Hammett substituent constants sigma(+) of the groups at the para-position of the aniline units suggests that a linear free energy correlation exists for this self-assembly process. The strength of the binding between the crown ether and the thread-like ion can be fine-tuned over a narrow range by judicious choice of the substituting groups. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.132
• 作为产物：
  描述：

  2,2'-[氧基二(乙烯氧基)]二乙酰二氯 在 硼烷四氢呋喃络合物 作用下， 以 甲苯 为溶剂， 生成 10,22-Bis-(4-bromo-phenyl)-1,4,7,13,16,19-hexaoxa-10,22-diaza-cyclotetracosane
  参考文献：
  名称：

  Substituent effects in the binding of bis(4-fluorobenzyl)ammonium ions by dianilino[24]crown-8

  摘要：

  A series of para-substituted dianilino[24]crown-8 (DA24C8) macrocycles were synthesized and their ability to form host-guest complexes with bis(4-fluorobenzyl)ammonium ions (DFA(+)) were investigated. Although these crown ethers contain weakly hydrogen bonding aniline motifs, they do bind DFA(+) in CDCl3/CD3NO2 solution, presumably in a pseudo rotaxane-like manner. A plot of the values of the relative binding strengths (log[K-a(R)/K-a(H)]) versus the Hammett substituent constants sigma(+) of the groups at the para-position of the aniline units suggests that a linear free energy correlation exists for this self-assembly process. The strength of the binding between the crown ether and the thread-like ion can be fine-tuned over a narrow range by judicious choice of the substituting groups. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.132

文献信息

• Substituent effects in the binding of bis(4-fluorobenzyl)ammonium ions by dianilino[24]crown-8
  作者：Sheng-Hsien Chiu、Kang-Shyang Liao、Jen-Kuan Su

  DOI：10.1016/j.tetlet.2003.10.132

  日期：2004.1

  A series of para-substituted dianilino[24]crown-8 (DA24C8) macrocycles were synthesized and their ability to form host-guest complexes with bis(4-fluorobenzyl)ammonium ions (DFA(+)) were investigated. Although these crown ethers contain weakly hydrogen bonding aniline motifs, they do bind DFA(+) in CDCl3/CD3NO2 solution, presumably in a pseudo rotaxane-like manner. A plot of the values of the relative binding strengths (log[K-a(R)/K-a(H)]) versus the Hammett substituent constants sigma(+) of the groups at the para-position of the aniline units suggests that a linear free energy correlation exists for this self-assembly process. The strength of the binding between the crown ether and the thread-like ion can be fine-tuned over a narrow range by judicious choice of the substituting groups. (C) 2003 Elsevier Ltd. All rights reserved.