11-[(2-benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester | 957829-85-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 11-[(2-benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
• 英文别名: Tritert-butyl 11-[2-oxo-2-[2-(phenylmethoxycarbonylamino)ethylamino]ethyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate
• CAS: 957829-85-5
• 化学式: C₃₇H₆₂N₆O₉
• 分子量: 734.934
• InChiKey: DHJXEUHKNXFYPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  11-[(2-benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 11-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
  参考文献：
  名称：

  Effective Methods for the Biotinylation of Azamacrocycles

  摘要：

  The biotin-(strept)avidin interaction remains a gold standard of model biological recognition events. The biotinylation of azarnacrocycles permits the investigation of signal transduction between this recognition event and the metal center of an azamacrocycle complex, of wide potential interest in biosensing. There are no generally applicable procedures in the literature for such functionalizations. We report here a comprehensive investigation into the attachment of biotin to TACN, cyclen, and cyclam.. Effective methods have been found for each ring. The efficacy of the functionalization is critically dependent on the nature of the azarnacrocycle.

  DOI：

  10.1021/jo071175v
• 作为产物：
  描述：

  1,4,8-三(叔丁氧碳酰)-1,4,8,11-四氮杂环十四烷 在 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 11-[(2-benzyloxycarbonylamino-ethylcarbamoyl)-methyl]-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
  参考文献：
  名称：

  Effective Methods for the Biotinylation of Azamacrocycles

  摘要：

  The biotin-(strept)avidin interaction remains a gold standard of model biological recognition events. The biotinylation of azarnacrocycles permits the investigation of signal transduction between this recognition event and the metal center of an azamacrocycle complex, of wide potential interest in biosensing. There are no generally applicable procedures in the literature for such functionalizations. We report here a comprehensive investigation into the attachment of biotin to TACN, cyclen, and cyclam.. Effective methods have been found for each ring. The efficacy of the functionalization is critically dependent on the nature of the azarnacrocycle.

  DOI：

  10.1021/jo071175v