1,8-dihydroxy-9-phenyl-9H-2,4,5,7-tetraazaxanthene | 155375-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,8-dihydroxy-9-phenyl-9H-2,4,5,7-tetraazaxanthene
• 英文别名: 5-phenylpyrano[2,3-d:6,5-d']dipyrimidine-4,6-dione；9-phenyl-2-oxa-4,6,12,14-tetrazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8),4,13-tetraene-7,11-dione
• CAS: 155375-99-8
• 化学式: C₁₅H₁₀N₄O₃
• 分子量: 294.269
• InChiKey: UDZRRRRTMBRJHA-UHFFFAOYSA-N

物化性质

• 密度：
  1.63±0.1 g/cm3(Predicted)
• 溶解度：
  >44.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1,8-dihydroxy-9-phenyl-9H-2,4,5,7-tetraazaxanthene 在 硫酸氢铵 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 15.25h， 生成 3,7-bis(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1134/s1070363207040159
• 作为产物：
  描述：

  5,5'-benzylidenebis(4,6-dihydroxypyrimidine) 在 乙酸酐 、 溶剂黄146 作用下， 以80%的产率得到1,8-dihydroxy-9-phenyl-9H-2,4,5,7-tetraazaxanthene
  参考文献：
  名称：

  Moskvin, A. V.; Petrova, N. M.; Semenova, E. A., Russian Journal of General Chemistry, 1993, vol. 63, # 9.2, p. 1454 - 1459

  摘要：

  DOI：

文献信息

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

  DOI：——

  日期：——
• 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.
• 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.
• Moskvin, A. V.; Petrova, N. M.; Semenova, E. A., Russian Journal of General Chemistry, 1993, vol. 63, # 9.2, p. 1454 - 1459
  作者：Moskvin, A. V.、Petrova, N. M.、Semenova, E. A.、Shopova, M.、Gindin, V. A.、Ivin, B. A.

  DOI：——

  日期：——