3-(ω-bromopentyl)-6-methyluracil | 68808-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-(ω-bromopentyl)-6-methyluracil
• 英文别名: 3-(5-bromopentyl-1)-6-methyluracil；3-(5-bromopentyl)-6-methyluracil；3-(5-bromopentyl)-6-methyl-1H-pyrimidine-2,4-dione
• CAS: 68808-04-8
• 化学式: C₁₀H₁₅BrN₂O₂
• 分子量: 275.145
• InChiKey: SSUZTBPYULDFRM-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C(Solv: benzene (71-43-2))
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(ω-bromopentyl)-6-methyluracil 生成 3-(ω-bromopentyl)-6-methyluracil sodium salt
  参考文献：
  名称：

  SALIXOV, I. SH.;REZNIK, V. S.;SHVETSOV, YU. S.;PETROVA, V. V.;SHAGIDULLIN+, IZV. AN CCCP. CEP. XIM., 1986, N 5, 1173-1177

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-二溴戊烷 、 6-methyl-2,4-bis(trimethylsiloxy)pyrimidine 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以20%的产率得到1-(5-bromopentyl)-6-methyluracil
  参考文献：
  名称：

  Synthesis of acyclic and macrocyclic analogs of Di-, Tri-, and tetranucleotides

  摘要：

  Compounds consisting of two or three uracil fragments were synthesized by reaction of methyl-substituted uracil sodium salts with 1-(6-bromohexyl)-3,6-dimethyluracil or 1,6-dibromohexane. Treatment of these compounds with paraformaldehyde gave the corresponding pyrimidinophanes and acyclic compounds in which the uracil fragments are linked through methylene bridges. Uracil derivatives having no substituent on N-3 were synthesized by reactions of silylated uracils with 1,3-bis(6-bromohexyl)uracil or 4,4'-(6-bromohexyloxy)diphenylmethane. The acyclic compound was converted into pyrimidinophane containing uracil fragments with (NH)-H-3 groups. A trinucleotide analog including uracil and two adenine fragments was synthesized from 1,3-bis(6-bromohexyl)uracil.

  DOI：

  10.1134/s1070363207080233

文献信息

• Synthesis of some polycyclic noncondensed pyrimidine structures
  作者：V. S. Reznik、I. Sh. Salikhov、Yu. S. Shvetsov、Yu. Ya. Efremov、I. Kh. Rizvanov

  DOI：10.1007/bf00702146

  日期：1995.2

  Methods for the synthesis of compounds containing two or more pyrimidine rings linked through aliphatic chains with different numbers of carbon atoms are described.

  描述了合成含有通过具有不同碳原子数的脂肪链连接的两个或多个嘧啶环的化合物的方法。
• Supramolecular systems based on dicationic pyrimidine-containing surfactants and polyethyleneimine
  作者：D. R. Gabdrakhmanov、D. A. Samarkina、F. G. Valeeva、L. F. Saifina、V. E. Semenov、V. S. Reznik、L. Ya. Zakharova、A. I. Konovalov

  DOI：10.1007/s11172-015-0902-x

  日期：2015.3

  Aggregates based on a novel pyrimidine-containing amphiphile containing three uracil fragments were quantitatively characterized. The critical micelle concentration (CMC) is 2 mmol L–1 and the degree of binding of counterions is β = 0.95, which is consistent with the low zeta potential of the micelles equal to +5 mV. Aggregates with a diameter of 45 nm are formed in the CMC region, and in the region of higher concentrations the aggregates are rearranged to micelle-like particles. In the presence of hydrophilic polymer polyethyleneimine, the CMC significantly decreases (to 0.2 mmol L–1), the degree of binding of counterions decreases, and the electrokinetic potential increases. The size of the aggregates in the binary system is 6—7 nm.

  对一种新型含嘧啶双亲化合物（含三个尿嘧啶片段）的聚集体进行了定量表征。临界胶束浓度（CMC）为 2 mmol L-1，反离子结合度为 β = 0.95，这与胶束的低 ZETA 电位（+5 mV）相一致。在 CMC 区域形成了直径为 45 nm 的聚集体，在浓度较高的区域，聚集体重新排列成胶束状颗粒。在亲水性聚合物聚乙烯亚胺的存在下，CMC 明显降低（降至 0.2 mmol L-1），反离子结合度降低，电动势增加。二元体系中的聚合体大小为 6-7 nm。
• Reaction of Na salts of some hydroxypyrimidines with ?, ?-dibromoalkanes
  作者：V. S. Reznik、I. Sh. Salikhov、Yu. S. Shvetsov、B. E. Ivanov

  DOI：10.1007/bf00949232

  日期：1980.11
• SHVETSOV YU. S.; SHIRSHOV A. N.; REZNIK V. S., IZV. AN CCCP. CEP. XIM., 1978, HO 9, 2079-2084
  作者：SHVETSOV YU. S.、 SHIRSHOV A. N.、 REZNIK V. S.

  DOI：——

  日期：——
• Synthesis of acyclic and macrocyclic analogs of Di-, Tri-, and tetranucleotides
  作者：V. E. Semenov、V. D. Akamsin、V. S. Reznik

  DOI：10.1134/s1070363207080233

  日期：2007.8

  Compounds consisting of two or three uracil fragments were synthesized by reaction of methyl-substituted uracil sodium salts with 1-(6-bromohexyl)-3,6-dimethyluracil or 1,6-dibromohexane. Treatment of these compounds with paraformaldehyde gave the corresponding pyrimidinophanes and acyclic compounds in which the uracil fragments are linked through methylene bridges. Uracil derivatives having no substituent on N-3 were synthesized by reactions of silylated uracils with 1,3-bis(6-bromohexyl)uracil or 4,4'-(6-bromohexyloxy)diphenylmethane. The acyclic compound was converted into pyrimidinophane containing uracil fragments with (NH)-H-3 groups. A trinucleotide analog including uracil and two adenine fragments was synthesized from 1,3-bis(6-bromohexyl)uracil.