1,3-bis(1-uracilmethyl)benzene | 251653-94-8

• 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: 1,3-bis(1-uracilmethyl)benzene
• 英文别名: 1-[[3-[(2,4-Dioxopyrimidin-1-yl)methyl]phenyl]methyl]pyrimidine-2,4-dione
• CAS: 251653-94-8
• 化学式: C₁₆H₁₄N₄O₄
• 分子量: 326.312
• InChiKey: FOHFDQFGNKKOJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(1-uracilmethyl)benzene 、 间二溴苄 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以24%的产率得到1,9,13,21-Tetrazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-3(28),4,6,11,15,17,19(26),22-octaene-10,24,25,27-tetrone
  参考文献：
  名称：

  Heterocalixarenes. 1. Calix[2]uracil[2]arene:  Synthesis, X-ray Structure, Conformational Analysis, and Binding Character

  摘要：

  1,3-Bis[(1-uracilyl)methyl)]benzene derivatives 3, formed by selective N-1 alkylation of 1,3-bis(trimethylsilyloxy)pyrimidine with 1,3-bis(bromomethyl)benzene derivatives 2, on cyclization with the same or different derivative of 2, provide calix[2]uracil[2]arenes 4. Their conformations, investigated through X-ray, variable temperature H-1 NMR, and molecular modeling MM2 calculations, are found to depend on the nature of substituent(s) on the position 2 of 1,3-phenylene rings. 4a exists in equilibrium between various conformations, and 4b, 4d-4i adopt an inward flattened partial cone conformation. In 4j, the equilibrium is restricted to two conformations at -60 degrees C, but the 4j ethanol complex (2:1), in the solid state, has a cone conformation with ethanol being a H-bond donor through H of OH and CH2 and an acceptor through O of OH. 4d, 4j, and 4k exhibit significant preferences toward alkaline earth metal ions over alkali metal ions though overall bindings are poor.

  DOI：

  10.1021/jo990085q
• 作为产物：
  描述：

  2,4-二(三甲硅氧基)嘧啶 、 间二溴苄 在 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以60%的产率得到1,3-bis(1-uracilmethyl)benzene
  参考文献：
  名称：

  Heterocalixarenes. 1. Calix[2]uracil[2]arene:  Synthesis, X-ray Structure, Conformational Analysis, and Binding Character

  摘要：

  1,3-Bis[(1-uracilyl)methyl)]benzene derivatives 3, formed by selective N-1 alkylation of 1,3-bis(trimethylsilyloxy)pyrimidine with 1,3-bis(bromomethyl)benzene derivatives 2, on cyclization with the same or different derivative of 2, provide calix[2]uracil[2]arenes 4. Their conformations, investigated through X-ray, variable temperature H-1 NMR, and molecular modeling MM2 calculations, are found to depend on the nature of substituent(s) on the position 2 of 1,3-phenylene rings. 4a exists in equilibrium between various conformations, and 4b, 4d-4i adopt an inward flattened partial cone conformation. In 4j, the equilibrium is restricted to two conformations at -60 degrees C, but the 4j ethanol complex (2:1), in the solid state, has a cone conformation with ethanol being a H-bond donor through H of OH and CH2 and an acceptor through O of OH. 4d, 4j, and 4k exhibit significant preferences toward alkaline earth metal ions over alkali metal ions though overall bindings are poor.

  DOI：

  10.1021/jo990085q

文献信息

• Heterocalixarenes. 1. Calix[2]uracil[2]arene:  Synthesis, X-ray Structure, Conformational Analysis, and Binding Character
  作者：Subodh Kumar、Geeta Hundal、Dharam Paul、Maninder Singh Hundal、Harjit Singh

  DOI：10.1021/jo990085q

  日期：1999.10.1

  1,3-Bis[(1-uracilyl)methyl)]benzene derivatives 3, formed by selective N-1 alkylation of 1,3-bis(trimethylsilyloxy)pyrimidine with 1,3-bis(bromomethyl)benzene derivatives 2, on cyclization with the same or different derivative of 2, provide calix[2]uracil[2]arenes 4. Their conformations, investigated through X-ray, variable temperature H-1 NMR, and molecular modeling MM2 calculations, are found to depend on the nature of substituent(s) on the position 2 of 1,3-phenylene rings. 4a exists in equilibrium between various conformations, and 4b, 4d-4i adopt an inward flattened partial cone conformation. In 4j, the equilibrium is restricted to two conformations at -60 degrees C, but the 4j ethanol complex (2:1), in the solid state, has a cone conformation with ethanol being a H-bond donor through H of OH and CH2 and an acceptor through O of OH. 4d, 4j, and 4k exhibit significant preferences toward alkaline earth metal ions over alkali metal ions though overall bindings are poor.