19-bromo-9-(4-methoxybenzyl)-1,9,17-triazatetracyclo[15.3.1.1(3,7).1(11,15)]tricosa-3(4),5,7(22),11(12),13,15(23),19-heptaene-18,21-dione | 1072195-97-1

• 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: 19-bromo-9-(4-methoxybenzyl)-1,9,17-triazatetracyclo[15.3.1.1(3,7).1(11,15)]tricosa-3(4),5,7(22),11(12),13,15(23),19-heptaene-18,21-dione
• 英文别名: 5-Bromo-15-[(4-methoxyphenyl)methyl]-3,7,15-triazatetracyclo[15.3.1.13,7.19,13]tricosa-1(21),5,9(22),10,12,17,19-heptaene-4,23-dione
• CAS: 1072195-97-1
• 化学式: C₂₈H₂₆BrN₃O₃
• 分子量: 532.437
• InChiKey: YZXMQWKXAZAQBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-bis[(3-bromomethylphenyl)methyl]-5-bromouracil 、 4-甲氧基苄胺 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 正丁醇 为溶剂， 以4%的产率得到19-bromo-9-(4-methoxybenzyl)-1,9,17-triazatetracyclo[15.3.1.1(3,7).1(11,15)]tricosa-3(4),5,7(22),11(12),13,15(23),19-heptaene-18,21-dione
  参考文献：
  名称：

  Synthesis of pyrimidinocyclophanes having a bridging nitrogen atom

  摘要：

  Reactions of 1,3-bis(omega-bromoalkyl)-substituted uracils, quinazoline-2,4-dione, and 5-methyl-1,3,5-triazine-2,4,6-trione and 1,3-bis(m-bromomethylbenzyl)-5-bromouracil with amines (aliphatic amines, benzylamines, naphthylmethanamine, and anisidine) gave a series of macrocyclic compounds having one pyrimidine or triazine fragment and an azapolymethylene bridge connecting the N-1 and N-3 atoms of the heteroring. The bridging nitrogen atom in some macrocyclic compounds was subjected to quaternization with methyl p-toluenesulfonate.

  DOI：

  10.1134/s1070428008060183

文献信息

• Macrocyclic 5-bromouracil derivatives: synthesis and transformation of a uracil ring
  作者：Anton E. Nikolaev、Vyacheslav E. Semenov、Dilyara R. Sharafutdinova、Yurii Ya. Efremov、Vladimir S. Reznik

  DOI：10.1016/j.tetlet.2008.07.164

  日期：2008.10

  Cyclization of 1,3-bis(ω-bromoalkyl)-5-bromouracil with p-methoxybenzylamine or sodium sulfide led to a series of pyrimidinophanes containing heteroatoms in bridges. An unusual behaviour of the 5-bromouracil ring, namely its contraction into hydantoin units during the cyclization reactions with p-methoxybenzylamine was observed. Sodium sulfide does not affect the 5-bromouracil ring, and no transformation

  1,3-双（ω-溴烷基）-5-溴尿嘧啶与对-甲氧基苄胺或硫化钠的环化反应导致一系列在桥中含有杂原子的嘧啶二甲基吡啶。观察到5-溴尿嘧啶环的异常行为，即在与对甲氧基苄胺的环化反应中，其收缩成乙内酰脲单位。硫化钠不影响5-溴尿嘧啶环，并且在具有硫桥的嘧啶并噻吩的合成中未观察到转化产物。给出了可能的反应机理。