1,6-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)hexane | 1020072-81-4

• 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: 1,6-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)hexane
• 英文别名: 1,1'-(hexane-1,6-diyl)bis(3,6-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione)；1-[6-(3,6-dimethyl-2,4-dioxopyrimidin-1-yl)hexyl]-3,6-dimethylpyrimidine-2,4-dione
• CAS: 1020072-81-4
• 化学式: C₁₈H₂₆N₄O₄
• 分子量: 362.429
• InChiKey: JSXUAABAXQHBOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)hexane 、 聚合甲醛 在 盐酸 作用下， 反应 6.0h， 以60%的产率得到bis[3,6-dimethyl-1-[6-(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)hexyl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]methane
  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
• 作为产物：
  描述：

  1,6-二溴己烷 、 3,6-dimethyluracil sodium salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以48%的产率得到1,6-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)hexane
  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

• α,ω-Bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)alkanes and products of their cyclization, pyrimidinophanes: intra- and intermolecular interaction in crystals and in solutions
  作者：V. E. Semenov、O. A. Lodochnikova、A. T. Gubaidullin、O. N. Kataeva、A. V. Chernova、Y. Ya. Efremov、S. V. Kharlamov、Sh. K. Latypov、V. S. Reznik

  DOI：10.1007/s11172-008-0019-6

  日期：2008.1

  the presence of intramolecular interactions in chloroform solutions of α,ω-bis(3,6-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)alkanes and pyrimidinophanes were made based on the UV spectra, which were interpreted in terms of hypo- and hyperchromic effects relatively to the model uracil derivative. These conclusions correlate with the X-ray data: there are no intramolecular π-π contacts between

  α,ω-双（3,6-二甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-1-基）烷烃与多聚甲醛反应生成嘧啶烷，其中包含四个 3,6-二甲基尿嘧啶片段，通过亚甲基链相互连接。对晶体状态和溶液中“开放”和大环尿嘧啶衍生物的分子内和分子间相互作用进行了比较研究。根据核磁共振谱数据，氯仿溶液中没有“开放”和大环化合物的自缔合，而 X 射线数据揭示了这些晶体中 3,6-二甲基尿嘧啶碎片之间的分子间 π-π 接触。化合物。关于 α,ω-双(3,6-二甲基-2,4-二氧-1,2,3, 4-四氢嘧啶-1-基）烷烃和嘧啶并烷是基于紫外光谱制备的，根据相对于模型尿嘧啶衍生物的减色和增色效应进行解释。这些结论与 X 射线数据相关：晶体和“开放”化合物溶液中的 3,6-二甲基尿嘧啶片段之间没有分子内 π-π 接触，这些片段在分子中的相对位置嘧啶并烷的数量由聚亚甲基桥的长度定义。对于具有三亚甲基和六亚甲基链的大环，观