di-tert-butyl 12,15,18,52,55,58-hexaoxa-1,8,22,29,36,39,42,65-octaazaheptacyclo[27.19.13.5^36,42.1^3,7.1^23,27.1^30,34.1^44,48]heptaconta-3(70),4,6,23(69),24,26,30(68),31,33,44(62),45,47-dodecaene-39,65-dicarboxylate | 1352942-45-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: di-tert-butyl 12,15,18,52,55,58-hexaoxa-1,8,22,29,36,39,42,65-octaazaheptacyclo[27.19.13.5^36,42.1^3,7.1^23,27.1^30,34.1^44,48]heptaconta-3(70),4,6,23(69),24,26,30(68),31,33,44(62),45,47-dodecaene-39,65-dicarboxylate
• 英文别名: Ditert-butyl 11,14,47,50,53-pentaoxa-1,8,17,24,31,34,37,60-octazaheptacyclo[22.19.13.531,37.13,7.118,22.125,29.139,43]pentahexaconta-3(65),4,6,18,20,22(64),25,27,29(63),39(57),40,42-dodecaene-34,60-dicarboxylate；ditert-butyl 11,14,47,50,53-pentaoxa-1,8,17,24,31,34,37,60-octazaheptacyclo[22.19.13.531,37.13,7.118,22.125,29.139,43]pentahexaconta-3(65),4,6,18,20,22(64),25,27,29(63),39(57),40,42-dodecaene-34,60-dicarboxylate
• CAS: 1352942-45-0
• 化学式: C₆₂H₉₂N₈O₉
• 分子量: 1093.46
• InChiKey: LVEJROHFDXMEQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  79
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1,7-di(3-bromobenzyl)cyclen 在 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 di-tert-butyl 12,15,18,52,55,58-hexaoxa-1,8,22,29,36,39,42,65-octaazaheptacyclo[27.19.13.5^36,42.1^3,7.1^23,27.1^30,34.1^44,48]heptaconta-3(70),4,6,23(69),24,26,30(68),31,33,44(62),45,47-dodecaene-39,65-dicarboxylate
  参考文献：
  名称：

  Macrobicyclic and Macrotricyclic Derivatives of N,N’,N’’,N’’’-Tetrasubstituted Cyclen and Cyclam

  摘要：

  N,N',N '',N'''-Tetrabenzyl derivatives of cyclen and cyclam possessing two bromine atoms in trans-positioned phenyl rings were introduced in the Pd-catalyzed amination reactions with oxadiamines and polyamines to provide a wide series of macrobicyclic compounds with tetrabenzyl substituted cyclen and cyclam central moieties in yields up to 31%. Macrocycles based on 1,7-dibenzylcyclen were modified with two 3-bromobenzyl substituents and introduced in the Pd-catalyzed macrocyclization with di- and trioxadiamines to afford spherically shaped macrotricyclic cryptands in yields up to 33%. An alternative approach to isomeric macrotricyclic cryptands employed Pd-catalyzed amination of di(Boc)-di(3-bromobenzyl)cyclen followed by the dialkylation of the resulting bicycle with two bromobenzyl groups and final catalytic macrocyclization step (yields up to 24%).

  DOI：

  10.3987/com-14-s(k)71

文献信息

• Pd-catalyzed amination in the synthesis of cyclen-based macrotricycles
  作者：Sergei M. Kobelev、Alexei D. Averin、Alexei K. Buryak、Franck Denat、Roger Guilard、Irina P. Beletskaya

  DOI：10.1016/j.tetlet.2011.11.024

  日期：2012.1

  Three approaches to three types of cyclen-based macrotricycles have been elaborated starting from trans-bis(3-bromobenzyl)cyclen. The macrotricycles were synthesized via Pd-catalyzed amination. The first approach employed consecutive macrocyclization and benzylation steps giving a cage-like tricycle. In the second, cyclen amino groups were Boc-protected prior to formation of the second and the third rings. In the third method, macrotricycles were synthesized according to a one-step procedure using diazacrown ethers. (C) 2011 Elsevier Ltd. All rights reserved.
• Macrobicyclic and Macrotricyclic Derivatives of N,N’,N’’,N’’’-Tetrasubstituted Cyclen and Cyclam
  作者：Irina P. Beletskaya、Alexei D. Averin、Sergei M. Kobelev、Alexei K. Buryak、Andrei I. Vovk、Valerii P. Kukhar、Franck Denat、Roger Guilard

  DOI：10.3987/com-14-s(k)71

  日期：——

  N,N',N '',N'''-Tetrabenzyl derivatives of cyclen and cyclam possessing two bromine atoms in trans-positioned phenyl rings were introduced in the Pd-catalyzed amination reactions with oxadiamines and polyamines to provide a wide series of macrobicyclic compounds with tetrabenzyl substituted cyclen and cyclam central moieties in yields up to 31%. Macrocycles based on 1,7-dibenzylcyclen were modified with two 3-bromobenzyl substituents and introduced in the Pd-catalyzed macrocyclization with di- and trioxadiamines to afford spherically shaped macrotricyclic cryptands in yields up to 33%. An alternative approach to isomeric macrotricyclic cryptands employed Pd-catalyzed amination of di(Boc)-di(3-bromobenzyl)cyclen followed by the dialkylation of the resulting bicycle with two bromobenzyl groups and final catalytic macrocyclization step (yields up to 24%).