N1-(3-(benzyloxycarbonylamino)propyl)-1,2-diaminoethane | 142038-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N1-(3-(benzyloxycarbonylamino)propyl)-1,2-diaminoethane
• 英文别名: benzyl N-[3-(2-aminoethylamino)propyl]carbamate
• CAS: 142038-97-9
• 化学式: C₁₃H₂₁N₃O₂
• 分子量: 251.329
• InChiKey: TXPXJMLBLARBPX-UHFFFAOYSA-N

物化性质

• 沸点：
  431.9±35.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N1-(3-(benzyloxycarbonylamino)propyl)-1,2-diaminoethane 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 tert-butyl N-[3-[(9-chloroacridine-4-carbonyl)amino]propyl]-N-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]carbamate
  参考文献：
  名称：

  DNA-directed alkylating agents. 5. Acridinecarboxamide derivatives of (1,2-diaminoethane)dichloroplatinum(II)

  摘要：

  A series of acridine-2- and -4-carboxamide-linked analogues of PtenCl2 has been prepared and evaluated for biological activity against several tumor cell lines in vitro and in vivo. The platinum complexes were generally more cytotoxic than the corresponding ligands against wild-type P388 leukemia cells in vitro, with acridine-4-carboxamide complexes being the more effective. In contrast to cisplatin and PtenCl2, the complexes were equally active in vitro against both wild-type and cisplatin-resistant P388 lines. The 4-carboxamide complexes showed high levels of in vivo activity (ILS >100%) against wild-type P388 using a single-dose protocol, and one compound was also significantly active in vivo in a cisplatin-resistant line, against which cisplatin and PtenCl2 are inactive.

  DOI：

  10.1021/jm00094a008
• 作为产物：
  描述：

  3-(苄氧羰基氨基)-1-丙醇 在 吡啶 作用下， 以 吡啶 为溶剂， 反应 23.0h， 生成 N1-(3-(benzyloxycarbonylamino)propyl)-1,2-diaminoethane
  参考文献：
  名称：

  DNA-directed alkylating agents. 5. Acridinecarboxamide derivatives of (1,2-diaminoethane)dichloroplatinum(II)

  摘要：

  A series of acridine-2- and -4-carboxamide-linked analogues of PtenCl2 has been prepared and evaluated for biological activity against several tumor cell lines in vitro and in vivo. The platinum complexes were generally more cytotoxic than the corresponding ligands against wild-type P388 leukemia cells in vitro, with acridine-4-carboxamide complexes being the more effective. In contrast to cisplatin and PtenCl2, the complexes were equally active in vitro against both wild-type and cisplatin-resistant P388 lines. The 4-carboxamide complexes showed high levels of in vivo activity (ILS >100%) against wild-type P388 using a single-dose protocol, and one compound was also significantly active in vivo in a cisplatin-resistant line, against which cisplatin and PtenCl2 are inactive.

  DOI：

  10.1021/jm00094a008

文献信息

• Monoprotection of Triamines with Alkyl Phenyl Carbonates
  作者：Amanda B. Sølvhøj、Christian Tortzen、Jørn B. Christensen

  DOI：10.1080/00304948.2012.697748

  日期：2012.1

  the monoprotection of N1-(2-aminoethyl)-1,2-diaminoethane (1), N1-(3-aminopropyl)-1,3-diaminopropane (6) and N1-(2-aminoethyl)-1,3-diaminopropane (9), which are commercially available, inexpensive and interesting as building blocks for a new family of dendrimers. The regioselective acylation of polyamines has been the subject of considerable interest and is undoubtly related to the versatility of the

  从历史上看，我们一直对使用化学计量的试剂开发用于部分保护多胺并避免使用色谱纯化的简单程序感兴趣。我们之前描述了使用烷基苯基碳酸酯以一般到良好的产率对二胺和三胺进行单保护和双保护。1,2 烷基苯基碳酸酯易于大规模合成并且保质期长。 1 我们感兴趣在N1-(2-氨基乙基)-1,2-二氨基乙烷(1)、N1-(3-氨基丙基)-1,3-二氨基丙烷(6)和N1-(2-氨基乙基)-1,3-的单保护中二氨基丙烷 (9)，它们是可商购的、廉价且有趣的，可作为新的树枝状聚合物家族的构建单元。多胺的区域选择性酰化一直是人们相当感兴趣的主题，无疑与产品的多功能性以及化学家对分子对称性破坏的迷恋有关。由于多胺是多元胺，这表明部分质子化是为某些氨基提供临时保护的策略之一。然而，这种策略需要严格的 pH 控制和对单个 pKb 值的先验知识。Bruice 和 Willis 研究了无环脂肪族 α,ω-二胺与乙酸苯酯的单乙酰化反应，3