1,3-二甲基-5,6-二苯基嘧啶-2,4-二酮 | 55625-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1,3-二甲基-5,6-二苯基嘧啶-2,4-二酮
• 英文名称: 1,3-dimethyl-5,6-diphenylpyrimidin-2,4-dion
• 英文别名: 5,6-diphenyl-1,3-dimethyluracil；1,3-dimethyl-5,6-diphenyl-1H-pyrimidine-2,4-dione；1,3-Dimethyl-5,6-diphenyluracil；2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-5,6-diphenyl-；1,3-dimethyl-5,6-diphenylpyrimidine-2,4-dione
• CAS: 55625-99-5
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: BGCSFDKAHCRVDN-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  442.3±55.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  碘苯 、 1,3-dimethyl-5-phenyluracil 在 copper(I) bromide 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以47%的产率得到1,3-二甲基-5,6-二苯基嘧啶-2,4-二酮
  参考文献：
  名称：

  Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C–H bond activation

  摘要：

  A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.001

文献信息

• Nickelaverbindungen als zwischenkomplexe der [2+2+2′]-cycloaddition von alkinen mit isocyanaten zu 2-pyridonen
  作者：Heinz Hoberg、Benno W. Oster

  DOI：10.1016/s0022-328x(00)99836-x

  日期：1983.8

  Diphenylacetylene and phenylisocyanate react with TMEDA/Ni0 to give an azanickela-5-ring (IVa) which yields the azanickela-7-ring (IIb) with an activated alkyne.

  二苯乙炔和苯基异氰酸酯与TMEDA / Ni 0反应，生成氮杂尼克5环（IVa），生成带有活化炔烃的氮杂尼克7环（IIb）。
• HOBERG, H.;OSTER, B. W., J. ORGANOMET. CHEM., 1983, 252, N 3, 359-364
  作者：HOBERG, H.、OSTER, B. W.

  DOI：——

  日期：——
• CAPUANO L.; FISCHER W.; SCHEIDT H.; SCHNEIDER M., CHEM. BER., 1978, 111, NO 7, 2497-2509
  作者：CAPUANO L.、 FISCHER W.、 SCHEIDT H.、 SCHNEIDER M.

  DOI：——

  日期：——
• Regioselective arylation of uracil and 4-pyridone derivatives via copper(I) bromide mediated C–H bond activation
  作者：Chien Cheng、Yu-Chiao Shih、Hui-Ting Chen、Tun-Cheng Chien

  DOI：10.1016/j.tet.2012.11.001

  日期：2013.1

  A facile and effective synthesis of 6-aryluracil derivatives was accomplished by the direct C H bond activation for arylation. A series of 6-aryl-1,3-dimethyluracils were synthesized from the reaction of 1,3-dimethyluracil with various phenyl iodides in DMF, in the presence of copper(I) bromide as the catalyst and lithium tert-butoxide as the base. This methodology is applicable to a variety of 5-substituted uracils as well as 4-pyridone to provide direct accesses to versatile uracil and 4-pyridone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.