5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H)-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H)-dione
• 英文别名: 2-oxa-4,6,12,14-tetrazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,13-tetraene-7,11-dione
• 化学式: C₉H₆N₄O₃
• mdl: MFCD02925220
• 分子量: 218.172
• InChiKey: WUWRBEZQVJRRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H)-dione 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 4.0h， 以46%的产率得到4,6-dichloro-5H-pyrano[2,3-d:6,5-d']dipyrimidine
  参考文献：
  名称：

  Moskvin; Petrova; Krasnov, Russian Journal of General Chemistry, 1996, vol. 66, # 5, p. 803 - 810

  摘要：

  DOI：

文献信息

• Azines and azoles: CXXVII. Glycosylation of 5,7-dihydro-4H-pyrano-[2,3-d:6,5-d′]dipyrimidine-4,6(3H)-dione and its 5-phenyl-substituted analog
  作者：E. V. Fedorova、V. V. Kvasha、E. P. Studentsov、A. V. Moskvin、B. A. Ivin

  DOI：10.1134/s1070363207040159

  日期：2007.4

  Glycosylation of 5-phenylpyrano[2,3-d:6,5-d']dipyrimidine-4,6-diones through the corresponding di-O-trimethylsilyl derivative with excess 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose gives a mixture of 3-mono-and 3,7-bis(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-5-phenylpyrano[2,3-d:6,5-d]dipyrimidines; in the reaction with equimolar amounts of the reactants, only the monoriboside is formed. Isomeric N,N'-disubstituted pyranodipyrimidines, as well as mixtures of their mono- and disubstituted derivatives can be separated by fractional crystallization. The alkylation of pyrano[2,3-d: 6,5-d'] dipyrimidine-4,6-di one and its 5-phenyl-substituted derivative with 2-oxabutane-1,4-diyl diacetate provides an efficient procedure for the synthesis of acyclic analogs of glycosides based on pyrano[2,3-d:6,5-d']dipyrimidines.
• Azines and Azoles: CXXI. Alkylation of 5,7-Dihydro-4H-pyrano[2,3-d:6,5-d']- dipyrimidine-4,6(3H)-dione and Its 5-Phenyl Derivative
  作者：V. V. Kvasha、E. V. Fedorova、E. P. Studentsov、A. V. Moskvin、B. A. Ivin

  DOI：10.1023/b:rugc.0000042434.24683.c2

  日期：2004.6

  Methylation of 5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H)-dione and its 5-phenyl analog with dimethyl sulfate in the presence of LiOH in aqueous solution gives rise to the corresponding 3,7-dimethyl derivatives. The same isomers are formed by methylation of 5-phenyl-5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H)-dione with methyl iodide in the presence of K2CO3 in N,N-dimethylacetamide. However, with ethyl bromide, propyl iodide, or butyl bromide instead of methyl iodide, mixtures of 3,7- and 1,7-dialkyl-5-phenyl-5,7-dihydro-4H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6-diones were obtained.