10,22-Diphenyl-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane-9,23-dione | 257890-38-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 10,22-Diphenyl-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane-9,23-dione
• 英文别名: 10,22-diphenyl-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane-9,23-dione
• CAS: 257890-38-3
• 化学式: C₂₈H₃₈N₂O₈
• 分子量: 530.618
• InChiKey: KJMDTNKVFLRHDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  10,22-Diphenyl-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane-9,23-dione 在 硼烷四氢呋喃络合物 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 1-(4-formylphenyl)-13-phenyl-4,7,10,16,19,22-hexaoxa-1,13-diazacyclotetraeicosane
  参考文献：
  名称：

  Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams

  摘要：

  An unexpected reaction of 1,5-bis(arylamino)-3-oxapentanes 4, 21 and 22 with diglycolyl dichloride gave 24-membered macrocyclic tetralactams 18, 23 and 24 respectively, in a reaction involving two molecules of each reactant (2:2 process). This was in contrast to closely related reactions of alpha,omega-bis(arylamino)alkylethers 5 and 6 with diglycolyl, triglycolyl and tetraglycolyl dichlorides which yielded the macrocycles 9-14 by reaction of one molecule of each reactant (1:1 process). The phenyl nuclei in 14 and 18 were formylated to give 34, 35 and 36. The aldehydes, 35 and 36 were condensed with a quinoxaline fluorophore to yield the diene 37 and the tetraene 38 respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00892-3
• 作为产物：
  描述：

  N,N'-bisphenyl-3,6,9-trioxaundecanedicarboxamide 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 10,22-Diphenyl-1,4,7,13,16,19-hexaoxa-10,22-diazacyclotetracosane-9,23-dione
  参考文献：
  名称：

  Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams

  摘要：

  An unexpected reaction of 1,5-bis(arylamino)-3-oxapentanes 4, 21 and 22 with diglycolyl dichloride gave 24-membered macrocyclic tetralactams 18, 23 and 24 respectively, in a reaction involving two molecules of each reactant (2:2 process). This was in contrast to closely related reactions of alpha,omega-bis(arylamino)alkylethers 5 and 6 with diglycolyl, triglycolyl and tetraglycolyl dichlorides which yielded the macrocycles 9-14 by reaction of one molecule of each reactant (1:1 process). The phenyl nuclei in 14 and 18 were formylated to give 34, 35 and 36. The aldehydes, 35 and 36 were condensed with a quinoxaline fluorophore to yield the diene 37 and the tetraene 38 respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00892-3

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.
• Synthesis of some 24-membered tetralactam derivatives by an unexpectedly simple route, and some macrocyclic polyether dilactams
  作者：Shohreh Ghorbanian、Lina K. Mehta、John Parrick、Craig H. Robson

  DOI：10.1016/s0040-4020(99)00892-3

  日期：1999.12

  An unexpected reaction of 1,5-bis(arylamino)-3-oxapentanes 4, 21 and 22 with diglycolyl dichloride gave 24-membered macrocyclic tetralactams 18, 23 and 24 respectively, in a reaction involving two molecules of each reactant (2:2 process). This was in contrast to closely related reactions of alpha,omega-bis(arylamino)alkylethers 5 and 6 with diglycolyl, triglycolyl and tetraglycolyl dichlorides which yielded the macrocycles 9-14 by reaction of one molecule of each reactant (1:1 process). The phenyl nuclei in 14 and 18 were formylated to give 34, 35 and 36. The aldehydes, 35 and 36 were condensed with a quinoxaline fluorophore to yield the diene 37 and the tetraene 38 respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.