di-tert-butyl 4,10-bis(3-bromobenzyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate | 1352942-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: di-tert-butyl 4,10-bis(3-bromobenzyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate
• CAS: 1352942-38-1
• 化学式: C₃₂H₄₆Br₂N₄O₄
• 分子量: 710.55
• InChiKey: NKPKIMYUDBDCNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  65.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 4,10-bis(3-bromobenzyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate 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 24.0h， 生成 di-tert-butyl 8,17-bis(3-bromobenzyl)-11,14-dioxa-1,8,17,24,27,32-hexaazatetracyclo[22.5.5.1^3,7.1^18,22]hexatriaconta-3(36),4,6,18(35),19,21-hexaene-27,32-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
• 作为产物：
  描述：

  1,7-di(3-bromobenzyl)cyclen 、 二碳酸二叔丁酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到di-tert-butyl 4,10-bis(3-bromobenzyl)-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate
  参考文献：
  名称：

  Pd-catalyzed amination in the synthesis of cyclen-based macrotricycles

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.11.024